MiMeDB: Showing metabocard for PA(16:1(9Z)/0:0) (MMDBc0033263)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:41:30 UTC

Update Date

2022-08-31 22:33:33 UTC

Metabolite ID

MMDBc0033263

Metabolite Identification

Common Name

PA(16:1(9Z)/0:0)

Description

1-(9Z-hexadecenoyl)-glycero-3-phosphate is also known as LPA(16:1(9Z)/0:0). 1-(9Z-hexadecenoyl)-glycero-3-phosphate is considered to be practically insoluble (in water) and acidic. 1-(9Z-hexadecenoyl)-glycero-3-phosphate is a glycerophosphate lipid molecule

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241223002D          

 27 26  0  0  1  0            999 V2000
    7.6164    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3322    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0631    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
M  END

HMDB0062323
     RDKit          3D
1-(9Z-hexadecenoyl)-glycero-3-phosphate
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.7079   -1.4890    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3465   -1.7753   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6784   -0.4471   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3367   -0.7090   -1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5575    0.5428   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3095    1.3824   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    0.6577    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    1.0162    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.2122    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.8175    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031    1.1101    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405    0.7450    0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082   -0.1543   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -0.5397   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197   -1.2605   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -1.6006   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -1.2798   -1.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -2.2633   -0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -2.6671   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653   -1.5423   -0.8644 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8634   -0.8017   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5744   -0.7153    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4884    0.2955    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7940    1.2854    1.3928 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.4748    1.5655    2.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4998    2.7113    0.8750 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8669    0.4668    2.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2067   -0.7005   -0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3140   -2.4127    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5185   -1.0730    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7460   -2.4305    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5471   -2.2694   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5479    0.0439    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3499    0.1237   -1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7769   -1.3942   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489   -1.2565   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728    0.2290   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0505    1.1616   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2825    1.6879    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188    2.3149   -0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168   -0.2791    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226    0.3530    2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481    2.8505    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476    2.8248    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    2.6969   -0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    1.1829   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878    0.1862    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    1.7830    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570    1.7021    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    0.1816    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962   -1.0845   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    0.2906   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    0.3550   -1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -1.2168   -1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040   -2.1984    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964   -0.6822    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9145   -3.2510    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -3.4078   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3316   -1.9745   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0929    0.1677   -1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418   -0.1846    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9655   -1.3738    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8823    2.6675   -0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9420   -0.4951    2.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  6
 21 60  1  0
 22 61  1  0
 22 62  1  0
 26 63  1  0
 27 64  1  0
M  END


  Mrv0541 02241223002D          

 27 26  0  0  1  0            999 V2000
    7.6164    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3322    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0631    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033263

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/b8-7-/t18-/m1/s1

> <INCHI_KEY>
GLGQZYWTNAOWHT-JTHGQSKGSA-N

> <FORMULA>
C19H37O7P

> <MOLECULAR_WEIGHT>
408.4666

> <EXACT_MASS>
408.22769005

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.69680925237235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.5965521916666665

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
106.09699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062323
     RDKit          3D
1-(9Z-hexadecenoyl)-glycero-3-phosphate
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.7079   -1.4890    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3465   -1.7753   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6784   -0.4471   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3367   -0.7090   -1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5575    0.5428   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3095    1.3824   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    0.6577    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    1.0162    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.2122    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.8175    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031    1.1101    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405    0.7450    0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082   -0.1543   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -0.5397   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197   -1.2605   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -1.6006   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -1.2798   -1.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -2.2633   -0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -2.6671   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653   -1.5423   -0.8644 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8634   -0.8017   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5744   -0.7153    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4884    0.2955    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7940    1.2854    1.3928 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.4748    1.5655    2.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4998    2.7113    0.8750 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8669    0.4668    2.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2067   -0.7005   -0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3140   -2.4127    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5185   -1.0730    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7460   -2.4305    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5471   -2.2694   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5479    0.0439    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3499    0.1237   -1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7769   -1.3942   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489   -1.2565   -2.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728    0.2290   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0505    1.1616   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2825    1.6879    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188    2.3149   -0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168   -0.2791    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226    0.3530    2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481    2.8505    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476    2.8248    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    2.6969   -0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    1.1829   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878    0.1862    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    1.7830    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570    1.7021    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    0.1816    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962   -1.0845   -0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    0.2906   -1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    0.3550   -1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -1.2168   -1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040   -2.1984    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964   -0.6822    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9145   -3.2510    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -3.4078   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3316   -1.9745   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0929    0.1677   -1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418   -0.1846    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9655   -1.3738    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8823    2.6675   -0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9420   -0.4951    2.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  6
 21 60  1  0
 22 61  1  0
 22 62  1  0
 26 63  1  0
 27 64  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      14.217  15.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.217  14.368   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.884  13.598   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.884  12.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.550  11.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.550   9.748   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.216   8.978   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      20.886   8.978   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.219   6.668   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      24.887   5.128   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      27.554   6.668   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      28.888   7.438   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      30.222   8.208   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      29.658   6.105   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      28.118   8.772   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0062323
HETATM    1  C1  UNL     1      -9.708  -1.489   0.305  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.346  -1.775  -0.297  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.678  -0.447  -0.563  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.337  -0.709  -1.156  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.558   0.543  -1.472  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.310   1.382  -0.231  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.549   0.658   0.785  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.381   1.016   1.263  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.665   2.212   0.836  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.313   1.817   0.239  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.503   1.110   1.272  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.840   0.745   0.690  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.708  -0.154  -0.489  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.049  -0.540  -1.083  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.920  -1.261  -0.102  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.208  -1.601  -0.767  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.399  -1.280  -1.948  1.00  0.00           O  
HETATM   18  O2  UNL     1       5.180  -2.263  -0.086  1.00  0.00           O  
HETATM   19  C17 UNL     1       6.445  -2.667  -0.509  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.365  -1.542  -0.864  1.00  0.00           C  
HETATM   21  O3  UNL     1       6.863  -0.802  -1.896  1.00  0.00           O  
HETATM   22  C19 UNL     1       7.574  -0.715   0.398  1.00  0.00           C  
HETATM   23  O4  UNL     1       8.488   0.296   0.041  1.00  0.00           O  
HETATM   24  P1  UNL     1       8.794   1.285   1.393  1.00  0.00           P  
HETATM   25  O5  UNL     1       7.475   1.566   2.106  1.00  0.00           O  
HETATM   26  O6  UNL     1       9.500   2.711   0.875  1.00  0.00           O  
HETATM   27  O7  UNL     1       9.867   0.467   2.414  1.00  0.00           O  
HETATM   28  H1  UNL     1     -10.207  -0.701  -0.275  1.00  0.00           H  
HETATM   29  H2  UNL     1     -10.314  -2.413   0.406  1.00  0.00           H  
HETATM   30  H3  UNL     1      -9.518  -1.073   1.328  1.00  0.00           H  
HETATM   31  H4  UNL     1      -7.746  -2.431   0.353  1.00  0.00           H  
HETATM   32  H5  UNL     1      -8.547  -2.269  -1.282  1.00  0.00           H  
HETATM   33  H6  UNL     1      -7.548   0.044   0.429  1.00  0.00           H  
HETATM   34  H7  UNL     1      -8.350   0.124  -1.228  1.00  0.00           H  
HETATM   35  H8  UNL     1      -5.777  -1.394  -0.492  1.00  0.00           H  
HETATM   36  H9  UNL     1      -6.449  -1.256  -2.126  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.573   0.229  -1.872  1.00  0.00           H  
HETATM   38  H11 UNL     1      -6.050   1.162  -2.245  1.00  0.00           H  
HETATM   39  H12 UNL     1      -6.283   1.688   0.236  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.819   2.315  -0.510  1.00  0.00           H  
HETATM   41  H14 UNL     1      -5.017  -0.279   1.177  1.00  0.00           H  
HETATM   42  H15 UNL     1      -2.923   0.353   2.054  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.448   2.851   1.753  1.00  0.00           H  
HETATM   44  H17 UNL     1      -3.148   2.825   0.077  1.00  0.00           H  
HETATM   45  H18 UNL     1      -0.750   2.697  -0.106  1.00  0.00           H  
HETATM   46  H19 UNL     1      -1.563   1.183  -0.641  1.00  0.00           H  
HETATM   47  H20 UNL     1      -0.988   0.186   1.654  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.401   1.783   2.149  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.357   1.702   0.462  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.378   0.182   1.485  1.00  0.00           H  
HETATM   51  H24 UNL     1       0.196  -1.085  -0.185  1.00  0.00           H  
HETATM   52  H25 UNL     1       0.093   0.291  -1.313  1.00  0.00           H  
HETATM   53  H26 UNL     1       2.561   0.355  -1.481  1.00  0.00           H  
HETATM   54  H27 UNL     1       1.860  -1.217  -1.941  1.00  0.00           H  
HETATM   55  H28 UNL     1       2.404  -2.198   0.228  1.00  0.00           H  
HETATM   56  H29 UNL     1       3.096  -0.682   0.829  1.00  0.00           H  
HETATM   57  H30 UNL     1       6.915  -3.251   0.344  1.00  0.00           H  
HETATM   58  H31 UNL     1       6.373  -3.408  -1.359  1.00  0.00           H  
HETATM   59  H32 UNL     1       8.332  -1.974  -1.209  1.00  0.00           H  
HETATM   60  H33 UNL     1       7.093   0.168  -1.855  1.00  0.00           H  
HETATM   61  H34 UNL     1       6.642  -0.185   0.671  1.00  0.00           H  
HETATM   62  H35 UNL     1       7.965  -1.374   1.182  1.00  0.00           H  
HETATM   63  H36 UNL     1       9.882   2.667  -0.036  1.00  0.00           H  
HETATM   64  H37 UNL     1       9.942  -0.495   2.186  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8    8   41
CONECT    8    9   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   49   50
CONECT   13   14   51   52
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   57   58
CONECT   20   21   22   59
CONECT   21   60
CONECT   22   23   61   62
CONECT   23   24
CONECT   24   25   25   26   27
CONECT   26   63
CONECT   27   64
END

HMDB0062323
     RDKit          3D
1-(9Z-hexadecenoyl)-glycero-3-phosphate
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.7079   -1.4890    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3465   -1.7753   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6784   -0.4471   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3367   -0.7090   -1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5575    0.5428   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3095    1.3824   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    0.6577    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    1.0162    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653    2.2122    0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.8175    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5031    1.1101    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405    0.7450    0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082   -0.1543   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -0.5397   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197   -1.2605   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -1.6006   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -1.2798   -1.9483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -2.2633   -0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -2.6671   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653   -1.5423   -0.8644 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8634   -0.8017   -1.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Synonyms

Value	Source
1-(9Z)-Hexadecenoyl-sn-glycerol 3-phosphate	ChEBI
LPA(16:1(9Z)/0:0)	ChEBI
PA(16:1(9Z)/0:0)	ChEBI
1-(9Z)-Hexadecenoyl-sn-glycerol 3-phosphoric acid	Generator
1-(9Z-Hexadecenoyl)-glycero-3-phosphoric acid	Generator
1-(9Z-Hexadecenoyl)-glycero-3-phosphate	ChEBI

Molecular Formula

C₁₉H₃₇O₇P

Average Mass

408.4666

Monoisotopic Mass

408.22769005

IUPAC Name

[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/b8-7-/t18-/m1/s1

InChI Key

GLGQZYWTNAOWHT-JTHGQSKGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate (CHEBI:75070 )
Monoacylglycerophosphates (LMGP10050016 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	3.74	ALOGPS
logP	4.6	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	106.1 m³·mol⁻¹	ChemAxon
Polarizability	45.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0062323

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29368482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52929751

PDB ID

Not Available

ChEBI ID

75070

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. doi: 10.1038/323171a0. [PubMed:3748188 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.

Showing metabocard for PA(16:1(9Z)/0:0) (MMDBc0033263)

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Structure for #<Metabolite:0x00007f12406afa00>

3D Structure for #<Metabolite:0x00007f12406afa00>