MiMeDB: Showing metabocard for ÃŸ,ÃŸ-ergoannam (MMDBc0008613)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:24:40 UTC

Update Date

2022-08-31 06:28:52 UTC

MiMeDB ID

MMDBc0008613

Metabolite Identification

Common Name

ÃŸ,ÃŸ-ergoannam

Description

ss,ss-ergoannam belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam. Based on a literature review very few articles have been published on ss,ss-ergoannam.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103242D          

 49 54  0  0  1  0            999 V2000
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -1.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6798   -2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2802    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3831   -0.9019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 18  3  1  1  0  0  0
 18  6  1  0  0  0  0
 19  4  1  1  0  0  0
 19  7  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  1  0  0  0  0
 23 14  2  0  0  0  0
 23 22  1  0  0  0  0
 24 11  2  0  0  0  0
 25 12  1  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 20  1  0  0  0  0
 27 22  2  0  0  0  0
 27 24  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  1  0  0  0
 21 30  1  1  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 16  1  0  0  0  0
 34 24  1  0  0  0  0
 28 35  1  1  0  0  0
 35 30  2  0  0  0  0
 36  5  1  0  0  0  0
 36 17  1  0  0  0  0
 36 26  1  0  0  0  0
 37 13  1  0  0  0  0
 37 25  1  0  0  0  0
 37 33  1  0  0  0  0
 38 29  1  0  0  0  0
 38 31  1  0  0  0  0
 38 32  1  0  0  0  0
 30 39  1  4  0  0  0
 40 31  2  0  0  0  0
 41 32  2  0  0  0  0
 42 33  2  0  0  0  0
 18 43  1  6  0  0  0
 19 44  1  6  0  0  0
 21 45  1  6  0  0  0
 25 46  1  1  0  0  0
 47 26  1  0  0  0  0
 28 48  1  1  0  0  0
 29 49  1  6  0  0  0
M  END


  Mrv1652305152103242D          

 49 54  0  0  1  0            999 V2000
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -1.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6798   -2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2802    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3831   -0.9019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 18  3  1  1  0  0  0
 18  6  1  0  0  0  0
 19  4  1  1  0  0  0
 19  7  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  1  0  0  0  0
 23 14  2  0  0  0  0
 23 22  1  0  0  0  0
 24 11  2  0  0  0  0
 25 12  1  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 20  1  0  0  0  0
 27 22  2  0  0  0  0
 27 24  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  1  0  0  0
 21 30  1  1  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 16  1  0  0  0  0
 34 24  1  0  0  0  0
 28 35  1  1  0  0  0
 35 30  2  0  0  0  0
 36  5  1  0  0  0  0
 36 17  1  0  0  0  0
 36 26  1  0  0  0  0
 37 13  1  0  0  0  0
 37 25  1  0  0  0  0
 37 33  1  0  0  0  0
 38 29  1  0  0  0  0
 38 31  1  0  0  0  0
 38 32  1  0  0  0  0
 30 39  1  4  0  0  0
 40 31  2  0  0  0  0
 41 32  2  0  0  0  0
 42 33  2  0  0  0  0
 18 43  1  6  0  0  0
 19 44  1  6  0  0  0
 21 45  1  6  0  0  0
 25 46  1  1  0  0  0
 47 26  1  0  0  0  0
 28 48  1  1  0  0  0
 29 49  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008613

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(CC)[C@@]([H])(N=C(O)[C@@]1([H])CN(C)C2([H])CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1C(=O)[C@@]2([H])CCCN2C(=O)[C@]1([H])[C@@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C33H43N5O4/c1-6-18(3)28(32(41)38-29(19(4)7-2)33(42)37-13-9-12-25(37)31(38)40)35-30(39)21-14-23-22-10-8-11-24-27(22)20(16-34-24)15-26(23)36(5)17-21/h8,10-11,14,16,18-19,21,25-26,28-29,34H,6-7,9,12-13,15,17H2,1-5H3,(H,35,39)/t18-,19+,21-,25-,26?,28-,29+/m1/s1

> <INCHI_KEY>
IHDIXBZKTTXKMY-ADKHCRFMSA-N

> <FORMULA>
C33H43N5O4

> <MOLECULAR_WEIGHT>
573.738

> <EXACT_MASS>
573.331504885

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
63.731122608999726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
1.7076960499693252

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.241245983350613

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.723090082542765

> <JCHEM_PKA_STRONGEST_BASIC>
8.271776992237074

> <JCHEM_POLAR_SURFACE_AREA>
109.31

> <JCHEM_REFRACTIVITY>
161.84030000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.124   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.789   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.456   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.790  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.937  -4.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.311  -3.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.469  -4.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.456   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.123  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.123  -2.310   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      10.122   1.540   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      12.789  -3.080   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      12.789   0.000   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.123   2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      15.456  -3.080   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0      11.455   5.390   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      16.790   0.770   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.788   0.770   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      10.049  -1.684   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.787  -1.540   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      12.789   3.080   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      14.123   0.770   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5   36                                                            
CONECT    6    1   18                                                       
CONECT    7    2   19                                                       
CONECT    8   10   11                                                       
CONECT    9   12   13                                                       
CONECT   10    8   22                                                       
CONECT   11    8   24                                                       
CONECT   12    9   25                                                       
CONECT   13    9   37                                                       
CONECT   14   21   23                                                       
CONECT   15   20   26                                                       
CONECT   16   20   34                                                       
CONECT   17   21   36                                                       
CONECT   18    3    6   28   43                                             
CONECT   19    4    7   29   44                                             
CONECT   20   15   16   27                                                  
CONECT   21   14   17   30   45                                             
CONECT   22   10   23   27                                                  
CONECT   23   14   22   26                                                  
CONECT   24   11   27   34                                                  
CONECT   25   12   31   37   46                                             
CONECT   26   15   23   36   47                                             
CONECT   27   20   22   24                                                  
CONECT   28   18   32   35   48                                             
CONECT   29   19   33   38   49                                             
CONECT   30   21   35   39                                                  
CONECT   31   25   38   40                                                  
CONECT   32   28   38   41                                                  
CONECT   33   29   37   42                                                  
CONECT   34   16   24                                                       
CONECT   35   28   30                                                       
CONECT   36    5   17   26                                                  
CONECT   37   13   25   33                                                  
CONECT   38   29   31   32                                                  
CONECT   39   30                                                            
CONECT   40   31                                                            
CONECT   41   32                                                            
CONECT   42   33                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   21                                                            
CONECT   46   25                                                            
CONECT   47   26                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

Synonyms

Value	Source
(4R)-N-[(2R,3R)-1-[(3S,8AR)-3-[(2S)-butan-2-yl]-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0,.0,]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidate	Generator

Chemical Formula

C₃₃H₄₃N₅O₄

Average Molecular Weight

573.738

Monoisotopic Molecular Weight

573.331504885

IUPAC Name

(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

Traditional Name

(4R)-N-[(2R,3R)-1-[(3S,8aR)-3-[(2S)-butan-2-yl]-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-3-methyl-1-oxopentan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CC)[C@@]([H])(N=C(O)[C@@]1([H])CN(C)C2([H])CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1C(=O)[C@@]2([H])CCCN2C(=O)[C@]1([H])[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C33H43N5O4/c1-6-18(3)28(32(41)38-29(19(4)7-2)33(42)37-13-9-12-25(37)31(38)40)35-30(39)21-14-23-22-10-8-11-24-27(22)20(16-34-24)15-26(23)36(5)17-21/h8,10-11,14,16,18-19,21,25-26,28-29,34H,6-7,9,12-13,15,17H2,1-5H3,(H,35,39)/t18-,19+,21-,25-,26?,28-,29+/m1/s1

InChI Key

IHDIXBZKTTXKMY-ADKHCRFMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergopeptams. These are tripeptidic noncyclol ergot alkaloids. The structure of ergopeptams is similar to ergopeptines except that L-proline is exchanged by D-proline, and the tripeptide chain is a noncyclol lactam.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergopeptams

Alternative Parents

Substituents

Ergopeptam-skeleton
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Isoleucine or derivatives
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Alpha-amino acid amide
Alpha-amino acid or derivatives
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Benzenoid
Carboxylic acid imide, n-substituted
Piperazine
Tertiary carboxylic acid amide
Carboxylic acid imide
Dicarboximide
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary aliphatic amine
Amino acid or derivatives
Lactam
Carboxamide group
Tertiary amine
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.033 g/L	ALOGPS
logP	3.81	ALOGPS
logP	1.71	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	161.84 m³·mol⁻¹	ChemAxon
Polarizability	63.73 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29212567

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585358

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for ÃŸ,ÃŸ-ergoannam (MMDBc0008613)

MOL for #<Metabolite:0x00007f092007a550>

3D MOL for #<Metabolite:0x00007f092007a550>

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3D-SDF for #<Metabolite:0x00007f092007a550>

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Structure for #<Metabolite:0x00007f092007a550>

3D Structure for #<Metabolite:0x00007f092007a550>