NP-MRD: Showing NP-Card for (2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid (NP0152960)

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Record Information

Version

2.0

Created at

2022-09-02 09:32:39 UTC

Updated at

2022-09-02 09:32:39 UTC

NP-MRD ID

NP0152960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid

Description

Malassezindole A belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. (2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid is found in Malassezia furfur. Based on a literature review very few articles have been published on Malassezindole A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211322D          

 27 31  0  0  1  0            999 V2000
    1.2214   -2.2711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740   -1.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6374   -2.0793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.9489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9787   -0.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.4080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895    1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    1.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127    0.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387    0.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -0.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155    0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    1.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    3.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980    1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    0.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2982    0.6172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -0.4944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  4 27  1  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -2.7780    4.1316    1.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160    3.9221    1.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    4.8271    1.0975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285    2.7278    0.1671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2466    1.5628    0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.2380    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687   -0.2377   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8136   -1.4919   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1097   -1.8704   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -3.0487   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1385   -3.0843   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357   -2.0232    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.8454    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7958   -0.8069    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659    0.5939    0.0205 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7386   -0.0882   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9352   -0.4910   -1.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1402   -1.0735   -1.9924 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7804   -1.0819   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -1.5526   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4172   -1.4254    0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501   -0.8154    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212   -0.3440    1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044   -0.4670    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    1.8456   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725    2.1390   -1.7472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6743    2.6125   -0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299    4.8904    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6845    2.9457   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    1.5745    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239    1.6503    2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431   -2.0885   -0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2559   -3.8753   -1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7277   -3.9870   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9007   -2.0743    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6496    0.0112    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7262    0.9201    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -0.3371   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -1.4620   -2.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921   -2.0300   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3988   -1.7961    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.6957    2.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    0.1397    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273    2.3612   -2.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15 25  1  0
 25 26  1  0
 25 27  2  0
 27  4  1  0
 14  6  1  0
 24 16  1  0
 14  9  1  0
 24 19  1  0
  3 28  1  0
  4 29  1  6
  5 30  1  0
  5 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  1
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 26 44  1  0
M  END


  Mrv1652309022211322D          

 27 31  0  0  1  0            999 V2000
    1.2214   -2.2711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740   -1.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6374   -2.0793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.9489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9787   -0.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.4080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895    1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    1.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6127    0.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387    0.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -0.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155    0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9295    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    1.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    3.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980    1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    0.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2982    0.6172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -0.4944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  4 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1CC2=C(NC3=CC=CC=C23)C(C2=CNC3=CC=CC=C23)C(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C21H17N3O3/c25-20-18(14-10-22-15-7-3-1-6-12(14)15)19-13(9-17(24-20)21(26)27)11-5-2-4-8-16(11)23-19/h1-8,10,17-18,22-23H,9H2,(H,24,25)(H,26,27)/t17-,18?/m0/s1

> <INCHI_KEY>
ZPYSWVAWFDJYIM-ZENAZSQFSA-N

> <FORMULA>
C21H17N3O3

> <MOLECULAR_WEIGHT>
359.385

> <EXACT_MASS>
359.126991419

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.09823635703076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-hydroxy-5-(1H-indol-3-yl)-1H,2H,5H,6H-azepino[4,5-b]indole-2-carboxylic acid

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.371475147333333

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.803516021230394

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9688880810897804

> <JCHEM_PKA_STRONGEST_BASIC>
1.0322405323215542

> <JCHEM_POLAR_SURFACE_AREA>
101.47

> <JCHEM_REFRACTIVITY>
100.46570000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-hydroxy-5-(1H-indol-3-yl)-1H,2H,5H,6H-azepino[4,5-b]indole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       2.280  -4.239   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.498  -3.297   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.923  -3.881   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.291  -1.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.827  -1.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.286   0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.076   1.468   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.062   2.628   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.354   2.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.751   2.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.010   1.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.872   0.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.475  -0.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.216   0.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.602   1.675   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.078   3.140   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.172   4.386   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.078   5.632   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.542   5.156   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.876   5.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.210   5.156   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.210   3.616   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.876   2.846   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.542   3.616   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.715   0.611   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.157   1.152   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       4.577  -0.923   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    7   16   25                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   15   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    4                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₇N₃O₃

Average Mass

359.3850 Da

Monoisotopic Mass

359.12699 Da

IUPAC Name

(2S)-4-hydroxy-5-(1H-indol-3-yl)-1H,2H,5H,6H-azepino[4,5-b]indole-2-carboxylic acid

Traditional Name

(2S)-4-hydroxy-5-(1H-indol-3-yl)-1H,2H,5H,6H-azepino[4,5-b]indole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H]1CC2=C(NC3=CC=CC=C23)C(C2=CNC3=CC=CC=C23)C(O)=N1

InChI Identifier

InChI=1S/C21H17N3O3/c25-20-18(14-10-22-15-7-3-1-6-12(14)15)19-13(9-17(24-20)21(26)27)11-5-2-4-8-16(11)23-19/h1-8,10,17-18,22-23H,9H2,(H,24,25)(H,26,27)/t17-,18?/m0/s1

InChI Key

ZPYSWVAWFDJYIM-ZENAZSQFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Malassezia furfur	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-alkylindole
Pyrroloazepine
Indole
Indole or derivatives
Azepine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.98	ALOGPS
logP	3.37	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
pKa (Strongest Basic)	1.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	37.1 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid (NP0152960)

MOL for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

3D MOL for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

3D SDF for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

3D-SDF for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

PDB for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

3D PDB for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

SMILES for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

INCHI for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

Structure for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)

3D Structure for NP0152960 ((2s)-4-hydroxy-5-(1h-indol-3-yl)-1h,2h,5h,6h-azepino[4,5-b]indole-2-carboxylic acid)