MiMeDB: Showing metabocard for Malassezindole B (MMDBc0011993)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:39:20 UTC

Update Date

2022-08-31 06:33:50 UTC

Metabolite ID

MMDBc0011993

Metabolite Identification

Common Name

Malassezindole B

Description

Malassezindole B 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. Based on a literature review a significant number of articles have been published on Malassezindole B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152105392D          

 29 33  0  0  1  0            999 V2000
    3.9725   -0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0873    4.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    4.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2408    0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627   -0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979    3.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    4.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888    2.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    0.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    1.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    3.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -0.4718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5548    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    1.3607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9369    2.6192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.5312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525    0.1342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117   -1.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.8852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085    1.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    2.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036   -0.6234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  2  0  0  0  0
 16 11  1  0  0  0  0
 17  9  1  0  0  0  0
 18 13  2  0  0  0  0
 17 19  1  1  0  0  0
 21 14  1  6  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 23 18  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 21 28  1  1  0  0  0
 17 29  1  6  0  0  0
M  END


  Mrv1652305152105392D          

 29 33  0  0  1  0            999 V2000
    3.9725   -0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0873    4.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    4.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2408    0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627   -0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979    3.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416    4.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6993    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5917    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888    2.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    0.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    1.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    3.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -0.4718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5548    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    1.3607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9369    2.6192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.5312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525    0.1342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117   -1.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.8852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085    1.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    2.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036   -0.6234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  2  0  0  0  0
 16 11  1  0  0  0  0
 17  9  1  0  0  0  0
 18 13  2  0  0  0  0
 17 19  1  1  0  0  0
 21 14  1  6  0  0  0
 21 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 23 18  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 21 28  1  1  0  0  0
 17 29  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0011993

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H17N3O4/c25-19(26)17-9-13-11-5-1-4-8-16(11)23-18(13)21(28,20(27)24-17)14-10-22-15-7-3-2-6-12(14)15/h1-8,10,17,22-23,28H,9H2,(H,24,27)(H,25,26)/t17-,21-/m0/s1

> <INCHI_KEY>
GRSYCGMRONDEOH-UWJYYQICSA-N

> <FORMULA>
C21H17N3O4

> <MOLECULAR_WEIGHT>
375.384

> <EXACT_MASS>
375.121906039

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.80266106995113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.6412378789999997

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.258267388285919

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5971494893200555

> <JCHEM_PKA_STRONGEST_BASIC>
0.022737591670281554

> <JCHEM_POLAR_SURFACE_AREA>
121.7

> <JCHEM_REFRACTIVITY>
101.91270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S)-4,5-dihydroxy-5-(1H-indol-3-yl)-1H,2H,6H-azepino[4,5-b]indole-2-carboxylic 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       7.415  -0.392   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.030   7.508   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.686   8.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.916   1.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.904  -0.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.049   5.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.638   7.474   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.905   2.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.483  -0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.104   3.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.893   0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.726   5.181   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.353   0.502   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.425   3.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.618   5.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.394   1.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.947  -0.881   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.902   1.974   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.381  -2.313   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.135   1.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.470   2.540   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.749   4.889   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       4.164   2.858   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -0.098   0.250   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      -1.142  -2.539   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.339  -3.519   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.136   2.643   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.340   3.811   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      -0.567  -1.164   0.000  0.00  0.00           H+0
CONECT    1    4    5                                                       
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    1    8                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   15                                                       
CONECT    8    4   16                                                       
CONECT    9   13   17                                                       
CONECT   10   14   22                                                       
CONECT   11    5   13   16                                                  
CONECT   12    6   14   15                                                  
CONECT   13    9   11   18                                                  
CONECT   14   10   12   21                                                  
CONECT   15    7   12   22                                                  
CONECT   16    8   11   23                                                  
CONECT   17    9   19   24   29                                             
CONECT   18   13   21   23                                                  
CONECT   19   17   25   26                                                  
CONECT   20   21   24   27                                                  
CONECT   21   14   18   20   28                                             
CONECT   22   10   15                                                       
CONECT   23   16   18                                                       
CONECT   24   17   20                                                       
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29   17                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₁₇N₃O₄

Average Mass

375.384

Monoisotopic Mass

375.121906039

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H17N3O4/c25-19(26)17-9-13-11-5-1-4-8-16(11)23-18(13)21(28,20(27)24-17)14-10-22-15-7-3-2-6-12(14)15/h1-8,10,17,22-23,28H,9H2,(H,24,27)(H,25,26)/t17-,21-/m0/s1

InChI Key

GRSYCGMRONDEOH-UWJYYQICSA-N

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
Tertiary alcohol
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen 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	0.041 g/L	ALOGPS
logP	2.31	ALOGPS
logP	2.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	0.023	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	121.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.91 m³·mol⁻¹	ChemAxon
Polarizability	38.8 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101746398

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 Malassezindole B (MMDBc0011993)

MOL for #<Metabolite:0x00007f92526ff978>

3D MOL for #<Metabolite:0x00007f92526ff978>

3D SDF for #<Metabolite:0x00007f92526ff978>

3D-SDF for #<Metabolite:0x00007f92526ff978>

PDB for #<Metabolite:0x00007f92526ff978>

3D PDB for #<Metabolite:0x00007f92526ff978>

SMILES for #<Metabolite:0x00007f92526ff978>

INCHI for #<Metabolite:0x00007f92526ff978>

Structure for #<Metabolite:0x00007f92526ff978>

3D Structure for #<Metabolite:0x00007f92526ff978>