MiMeDB: Showing metabocard for NAD (MMDBc0029513)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:25 UTC

Update Date

2022-12-15 22:51:46 UTC

Metabolite ID

MMDBc0029513

Metabolite Identification

Common Name

NAD

Description

NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900232D          

 44 48  0  0  1  0            999 V2000
    5.1419    0.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -0.7835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6127    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.4144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1306    1.9060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -0.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8536   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1720   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.6462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351    2.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3828   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -0.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -1.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0382   -0.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6974   -0.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4186   -1.6123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0851   -2.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5073   -0.0263    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.8820   -2.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8782    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2908    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8745    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    1.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    2.4410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4580    1.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 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
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  6  0  0  0
 33 36  1  1  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
 37 39  2  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 40 41  2  0  0  0  0
M  CHG  1  35   1
M  END


  Mrv1652305271900232D          

 44 48  0  0  1  0            999 V2000
    5.1419    0.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -0.7835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6127    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.4144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1306    1.9060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -0.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8536   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1720   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.6462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351    2.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3828   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -0.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -1.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0382   -0.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6974   -0.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4186   -1.6123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0851   -2.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5073   -0.0263    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.8820   -2.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8782    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2908    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8745    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    1.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    2.4410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4580    1.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 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
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  6  0  0  0
 33 36  1  1  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
 37 39  2  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 40 41  2  0  0  0  0
M  CHG  1  35   1
M  END
> <DATABASE_ID>
MMDBc0029513

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
BAWFJGJZGIEFAR-NNYOXOHSSA-O

> <FORMULA>
C21H28N7O14P2

> <MOLECULAR_WEIGHT>
664.433

> <EXACT_MASS>
664.116946663

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.833807292893255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-9.866487273821402

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1873599316560752

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536300079335266

> <JCHEM_PKA_STRONGEST_BASIC>
4.009031974187107

> <JCHEM_POLAR_SURFACE_AREA>
318.2599999999999

> <JCHEM_REFRACTIVITY>
141.99689999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       9.598   1.097   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.143   1.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.211  -1.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.477   2.342   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.129   3.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.807   0.774   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       7.946  -0.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.747  -2.897   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.577   3.558   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.792   3.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.464   1.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.708  -1.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.193  -2.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.654  -4.135   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       5.457   3.073   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       6.786   5.379   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.267  -0.984   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.315  -4.135   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.036  -0.928   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       2.384  -0.921   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0       0.316  -0.928   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.384  -2.707   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.384   0.788   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      -1.596  -0.921   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      -3.242  -0.935   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.589  -2.630   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.596   0.795   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.838  -0.914   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.265  -1.413   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.538  -0.570   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.666  -2.974   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.768  -1.526   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.248  -3.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.759  -4.099   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0     -10.280  -0.049   0.000  0.00  0.00           N+1
HETATM   36  O   UNK     0      -9.113  -4.212   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -9.106   0.816   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -11.743   0.752   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.099   2.356   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -11.764   2.194   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.470   3.038   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.826   3.199   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -7.826   4.557   0.000  0.00  0.00           N+0
HETATM   44  O   UNK     0      -6.455   2.510   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   15                                                       
CONECT   12    7   17   13                                                  
CONECT   13    8   18   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10                                                            
CONECT   17   12   19                                                       
CONECT   18   13                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   24                                                       
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   21   25   26   27                                             
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29   33   34                                                  
CONECT   32   30   35   33                                                  
CONECT   33   31   36   32                                                  
CONECT   34   31                                                            
CONECT   35   32   37   38                                                  
CONECT   36   33                                                            
CONECT   37   35   39                                                       
CONECT   38   35   40                                                       
CONECT   39   37   41   42                                                  
CONECT   40   38   41                                                       
CONECT   41   39   40                                                       
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

Synonyms

Value	Source
beta-NAD	ChEBI
Diphosphopyridine nucleotide	ChEBI
DPN	ChEBI
NAD+	ChEBI
Nadide	ChEBI
Nicotinamide adenine dinucleotide	ChEBI
beta-NAD+	Kegg
b-NAD	Generator
Β-nad	Generator
b-NAD+	Generator
Β-nad+	Generator
3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt	HMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt	HMDB
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate	HMDB
3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate	HMDB
Adenine-nicotinamide dinucleotide	HMDB
beta-Diphosphopyridine nucleotide	HMDB
beta-Nicotinamide adenine dinucleotide	HMDB
beta-Nicotinamide adenine dinucleotide trihydrate	HMDB
CO-I	HMDB
Codehydrase I	HMDB
Codehydrogenase I	HMDB
Coenzyme I	HMDB
Cozymase	HMDB
Cozymase I	HMDB
Diphosphopyridine nucleotide oxidized	HMDB
Endopride	HMDB
NAD trihydrate	HMDB
NAD-oxidized	HMDB
Nicotinamide adenine dinucleotide oxidized	HMDB
Nicotinamide dinucleotide	HMDB
Nicotineamide adenine dinucleotide	HMDB
Oxidized diphosphopyridine nucleotide	HMDB
Pyridine nucleotide diphosphate	HMDB
[(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate	HMDB
[Adenylate-32-p]-NAD	HMDB
Dihydronicotinamide adenine dinucleotide	HMDB
NADH	HMDB
Nucleotide, diphosphopyridine	HMDB
Adenine dinucleotide, dihydronicotinamide	HMDB
Dinucleotide, dihydronicotinamide adenine	HMDB
Dinucleotide, nicotinamide-adenine	HMDB
Nicotinamide-adenine dinucleotide	HMDB

Molecular Formula

C₂₁H₂₈N₇O₁₄P₂

Average Mass

664.433

Monoisotopic Mass

664.116946663

IUPAC Name

1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

Traditional Name

1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

CAS Registry Number

53-84-9

SMILES

NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

BAWFJGJZGIEFAR-NNYOXOHSSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pyridine nucleotide
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Purine
Imidazopyrimidine
Nicotinamide
Monoalkyl phosphate
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Imidolactam
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Pyridinium
Pyridine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Carboximidic acid derivative
Carboximidic acid
Organoheterocyclic compound
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NAD(P)(+) (CHEBI:15846 )
NAD (CHEBI:15846 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-9.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	318.26 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142 m³·mol⁻¹	ChemAxon
Polarizability	55.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Endoplasmic reticulum
Extracellular
Mitochondria
Nucleus
Peroxisome

Biospecimen Locations

Adrenal Gland
Blood
Brain
Cellular Cytoplasm
Epidermis
Feces
Fibroblasts
Liver
Placenta
Platelet
Prostate
Skeletal Muscle

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
Pellagra	Slight Increase	Association	Human Blood	HMDB	17709435

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	727	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Goat feces; Sheep feces; River trout ; Cattle ; Rat ; Turkey ; Sheep ; Dog ; Lion ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	563	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle ; Catfish ; Goat feces; Sheep feces	Metabolic reconstruction
Bacteria	Actinobacteria	228	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	138	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	19	Human feces; Human ; Pig ; Relapsing fever tick	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	12	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Candidatus Melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	24	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	120	Human feces	Unknown
Archaea/Archaea	Crenarchaeota	22	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	19	Human feces
Bacteria	Aquificae	5
Archaea/Archaea	Euryarchaeota	44	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Archaea/Archaea	nah	11
Bacteria/NULL	Proteobacteria	15	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Goat feces; Sheep feces; River trout ; Cattle ; Rat ; Turkey ; Sheep ; Dog ; Lion ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Eukaryota/Fungi	Mucoromycota	4
Bacteria	Deinococcus-Thermus	8
Bacteria	Thermotogae	10
Bacteria	Cyanobacteria	24
Bacteria	nah	4	Human
Bacteria	Acidobacteria	3
Bacteria	Chlorobi	12
Bacteria	Chloroflexi	9
Bacteria	Dictyoglomi	2
Bacteria/NULL	Tenericutes	1	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Archaea/Archaea	Korarchaeota	1
Archaea/Archaea	Thaumarchaeota	2	Human feces	Metabolic reconstruction
Bacteria/NULL	Actinobacteria	7	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Elusimicrobia	1
Bacteria	Nitrospirae	1
Bacteria/NULL	Firmicutes	2	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle ; Catfish ; Goat feces; Sheep feces	Metabolic reconstruction
Archaea	nah	2
Bacteria	Gemmatimonadetes	1
Bacteria/NULL	nah	1	Human
Bacteria/NULL	Bacteroidetes	1	Human feces; Human appendix biopsy; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human	Detected and Quantified	0.0036			Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	HMDB	28792876
Human	Detected and Quantified	29.1	25.0	33.2	Adult (>18 years old)	Both	Pellagra	HMDB	17709435
Human	Detected and Quantified	88.7			Adult (>18 years old)	Both	Normal	HMDB	15882454
Human	Detected and Quantified	24.3	23.0	25.6	Adult (>18 years old)	Both	Normal	HMDB	17709435
Human Adrenal Gland	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal Muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000902

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15846

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Kunsman GW, Manno JE, Cockerham KR, Manno BR: A modification and validation of two urine ethanol procedures for use with the Monarch 2000 Chemistry System. J Anal Toxicol. 1991 May-Jun;15(3):130-5. doi: 10.1093/jat/15.3.130. [PubMed:1943056 ]
Krotz F, Sohn HY, Gloe T, Zahler S, Riexinger T, Schiele TM, Becker BF, Theisen K, Klauss V, Pohl U: NAD(P)H oxidase-dependent platelet superoxide anion release increases platelet recruitment. Blood. 2002 Aug 1;100(3):917-24. doi: 10.1182/blood.v100.3.917. [PubMed:12130503 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Hamza A, Cho H, Tai HH, Zhan CG: Understanding human 15-hydroxyprostaglandin dehydrogenase binding with NAD+ and PGE2 by homology modeling, docking and molecular dynamics simulation. Bioorg Med Chem. 2005 Jul 15;13(14):4544-51. doi: 10.1016/j.bmc.2005.04.053. [PubMed:15908215 ]
Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. doi: 10.1016/j.jmb.2005.05.014. [PubMed:15946682 ]
Begonja AJ, Gambaryan S, Geiger J, Aktas B, Pozgajova M, Nieswandt B, Walter U: Platelet NAD(P)H-oxidase-generated ROS production regulates alphaIIbbeta3-integrin activation independent of the NO/cGMP pathway. Blood. 2005 Oct 15;106(8):2757-60. doi: 10.1182/blood-2005-03-1047. Epub 2005 Jun 23. [PubMed:15976180 ]
Orczyk J, Morre DM, Morre DJ: Periodic fluctuations in oxygen consumption comparing HeLa (cancer) and CHO (non-cancer) cells and response to external NAD(P)+/NAD(P)H. Mol Cell Biochem. 2005 May;273(1-2):161-7. doi: 10.1007/s11010-005-0326-2. [PubMed:16013451 ]
Kim MY, Zhang T, Kraus WL: Poly(ADP-ribosyl)ation by PARP-1: 'PAR-laying' NAD+ into a nuclear signal. Genes Dev. 2005 Sep 1;19(17):1951-67. doi: 10.1101/gad.1331805. [PubMed:16140981 ]
Bruzzone S, Moreschi I, Guida L, Usai C, Zocchi E, De Flora A: Extracellular NAD+ regulates intracellular calcium levels and induces activation of human granulocytes. Biochem J. 2006 Feb 1;393(Pt 3):697-704. doi: 10.1042/BJ20051302. [PubMed:16225456 ]
Ying W: NAD+ and NADH in cellular functions and cell death. Front Biosci. 2006 Sep 1;11:3129-48. doi: 10.2741/2038. [PubMed:16720381 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for NAD (MMDBc0029513)

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