MiMeDB: Showing metabocard for N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl) (MMDBc0008043)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:01:23 UTC

Update Date

2022-08-31 06:28:02 UTC

Metabolite ID

MMDBc0008043

Metabolite Identification

Common Name

N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl)

Description

N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl) 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 N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103012D          

 51 57  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
    6.8513    2.4750    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
   10.4236   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -1.6500    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
    9.7092    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -1.2375    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
    8.2802    0.0000    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  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
    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  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
    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  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
    7.5658   -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
   -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
    8.2802   -1.6500    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
    6.1368    2.8875    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
    7.5658    0.4125    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
  4  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21  4  1  0  0  0  0
 22 10  2  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 26 17  2  0  0  0  0
 26 25  1  0  0  0  0
 27 13  2  0  0  0  0
 28 14  1  0  0  0  0
 29 18  1  0  0  0  0
 29 26  1  0  0  0  0
 30 16  1  1  0  0  0
 31 23  1  0  0  0  0
 31 25  2  0  0  0  0
 31 27  1  0  0  0  0
 32 21  1  0  0  0  0
 24 33  1  1  0  0  0
 34 30  1  0  0  0  0
 35 28  1  0  0  0  0
 36 32  1  0  0  0  0
 37 19  1  0  0  0  0
 37 27  1  0  0  0  0
 32 38  1  6  0  0  0
 38 33  2  0  0  0  0
 39  3  1  0  0  0  0
 39 20  1  0  0  0  0
 39 29  1  0  0  0  0
 40 15  1  0  0  0  0
 40 28  1  0  0  0  0
 40 34  1  0  0  0  0
 41 30  1  0  0  0  0
 41 35  1  0  0  0  0
 41 36  1  0  0  0  0
 33 42  1  4  0  0  0
 43 34  2  0  0  0  0
 44 35  2  0  0  0  0
 45 36  2  0  0  0  0
 46 21  1  0  0  0  0
 24 47  1  6  0  0  0
 28 48  1  1  0  0  0
 29 49  1  1  0  0  0
 30 50  1  6  0  0  0
 32 51  1  6  0  0  0
M  END


  Mrv1652305152103012D          

 51 57  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
    6.8513    2.4750    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
   10.4236   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -1.6500    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
    9.7092    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -1.2375    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
    8.2802    0.0000    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  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
    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  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
    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  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
    7.5658   -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
   -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
    8.2802   -1.6500    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
    6.1368    2.8875    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
    7.5658    0.4125    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
  4  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21  4  1  0  0  0  0
 22 10  2  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 26 17  2  0  0  0  0
 26 25  1  0  0  0  0
 27 13  2  0  0  0  0
 28 14  1  0  0  0  0
 29 18  1  0  0  0  0
 29 26  1  0  0  0  0
 30 16  1  1  0  0  0
 31 23  1  0  0  0  0
 31 25  2  0  0  0  0
 31 27  1  0  0  0  0
 32 21  1  0  0  0  0
 24 33  1  1  0  0  0
 34 30  1  0  0  0  0
 35 28  1  0  0  0  0
 36 32  1  0  0  0  0
 37 19  1  0  0  0  0
 37 27  1  0  0  0  0
 32 38  1  6  0  0  0
 38 33  2  0  0  0  0
 39  3  1  0  0  0  0
 39 20  1  0  0  0  0
 39 29  1  0  0  0  0
 40 15  1  0  0  0  0
 40 28  1  0  0  0  0
 40 34  1  0  0  0  0
 41 30  1  0  0  0  0
 41 35  1  0  0  0  0
 41 36  1  0  0  0  0
 33 42  1  4  0  0  0
 43 34  2  0  0  0  0
 44 35  2  0  0  0  0
 45 36  2  0  0  0  0
 46 21  1  0  0  0  0
 24 47  1  6  0  0  0
 28 48  1  1  0  0  0
 29 49  1  1  0  0  0
 30 50  1  6  0  0  0
 32 51  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008043

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(C)(CC)[C@]([H])(N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1C(=O)[C@@]2([H])CCCN2C(=O)[C@]1([H])CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H41N5O4/c1-4-21(2)32(36(45)41-30(16-22-10-6-5-7-11-22)34(43)40-15-9-14-28(40)35(41)44)38-33(42)24-17-26-25-12-8-13-27-31(25)23(19-37-27)18-29(26)39(3)20-24/h5-8,10-13,17,19,21,24,28-30,32,37H,4,9,14-16,18,20H2,1-3H3,(H,38,42)/t21?,24-,28-,29-,30+,32+/m1/s1

> <INCHI_KEY>
VIKMAEPJLMVSMP-KPLDYJOPSA-N

> <FORMULA>
C36H41N5O4

> <MOLECULAR_WEIGHT>
607.755

> <EXACT_MASS>
607.31585482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
67.05925503696534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-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>
3.98

> <JCHEM_LOGP>
2.006400471390019

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.912032135370485

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.628181862237802

> <JCHEM_PKA_STRONGEST_BASIC>
8.271697264331618

> <JCHEM_POLAR_SURFACE_AREA>
109.31

> <JCHEM_REFRACTIVITY>
172.86270000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-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      12.789   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.457  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.457  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.124  -3.080   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      18.124   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.790  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.311  -3.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.469  -4.586   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.456   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.790  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.655   2.016   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       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.123  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.123  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      10.122   1.540   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      12.789  -3.080   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      12.789   0.000   0.000  0.00  0.00           N+0
HETATM   42  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      15.456  -3.080   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      14.123   2.310   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0      11.455   5.390   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.788   0.770   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      10.049  -1.684   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.787  -1.540   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      14.123   0.770   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      12.789   3.080   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   21                                                            
CONECT    3   39                                                            
CONECT    4    1   21                                                       
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8   12   13                                                       
CONECT    9   14   15                                                       
CONECT   10    6   22                                                       
CONECT   11    7   22                                                       
CONECT   12    8   25                                                       
CONECT   13    8   27                                                       
CONECT   14    9   28                                                       
CONECT   15    9   40                                                       
CONECT   16   22   30                                                       
CONECT   17   24   26                                                       
CONECT   18   23   29                                                       
CONECT   19   23   37                                                       
CONECT   20   24   39                                                       
CONECT   21    2    4   32   46                                             
CONECT   22   10   11   16                                                  
CONECT   23   18   19   31                                                  
CONECT   24   17   20   33   47                                             
CONECT   25   12   26   31                                                  
CONECT   26   17   25   29                                                  
CONECT   27   13   31   37                                                  
CONECT   28   14   35   40   48                                             
CONECT   29   18   26   39   49                                             
CONECT   30   16   34   41   50                                             
CONECT   31   23   25   27                                                  
CONECT   32   21   36   38   51                                             
CONECT   33   24   38   42                                                  
CONECT   34   30   40   43                                                  
CONECT   35   28   41   44                                                  
CONECT   36   32   41   45                                                  
CONECT   37   19   27                                                       
CONECT   38   32   33                                                       
CONECT   39    3   20   29                                                  
CONECT   40   15   28   34                                                  
CONECT   41   30   35   36                                                  
CONECT   42   33                                                            
CONECT   43   34                                                            
CONECT   44   35                                                            
CONECT   45   36                                                            
CONECT   46   21                                                            
CONECT   47   24                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   32                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

Synonyms

Not Available

Molecular Formula

C₃₆H₄₁N₅O₄

Average Mass

607.755

Monoisotopic Mass

607.31585482

IUPAC Name

(4R,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-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,7R)-N-[(2S)-1-[(3S,8aR)-3-benzyl-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)[C@]2([H])CC3=CNC4=CC=CC(=C34)C2=C1)C(=O)N1C(=O)[C@@]2([H])CCCN2C(=O)[C@]1([H])CC1=CC=CC=C1

InChI Identifier

InChI=1S/C36H41N5O4/c1-4-21(2)32(36(45)41-30(16-22-10-6-5-7-11-22)34(43)40-15-9-14-28(40)35(41)44)38-33(42)24-17-26-25-12-8-13-27-31(25)23(19-37-27)18-29(26)39(3)20-24/h5-8,10-13,17,19,21,24,28-30,32,37H,4,9,14-16,18,20H2,1-3H3,(H,38,42)/t21?,24-,28-,29-,30+,32+/m1/s1

InChI Key

VIKMAEPJLMVSMP-KPLDYJOPSA-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
Benzoquinoline
Isoleucine or derivatives
N-acyl-alpha amino acid or derivatives
Quinoline-3-carboxamide
Pyrroloquinoline
Alpha-amino acid amide
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Isoindole or derivatives
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Aralkylamine
N-alkylpiperazine
Piperazine
Carboxylic acid imide, n-substituted
1,4-diazinane
Monocyclic benzene moiety
Benzenoid
Carboxylic acid imide
Dicarboximide
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Lactam
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Amine
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen 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	0.019 g/L	ALOGPS
logP	3.98	ALOGPS
logP	2.01	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.63	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	172.86 m³·mol⁻¹	ChemAxon
Polarizability	67.06 Å³	ChemAxon
Number of Rings	7	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
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View 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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585191

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 N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl) (MMDBc0008043)

MOL for #<Metabolite:0x00007f46a386a8f8>

3D MOL for #<Metabolite:0x00007f46a386a8f8>

3D SDF for #<Metabolite:0x00007f46a386a8f8>

3D-SDF for #<Metabolite:0x00007f46a386a8f8>

PDB for #<Metabolite:0x00007f46a386a8f8>

3D PDB for #<Metabolite:0x00007f46a386a8f8>

SMILES for #<Metabolite:0x00007f46a386a8f8>

INCHI for #<Metabolite:0x00007f46a386a8f8>

Structure for #<Metabolite:0x00007f46a386a8f8>

3D Structure for #<Metabolite:0x00007f46a386a8f8>