MiMeDB: Showing metabocard for Brevicompanine B (MMDBc0019049)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:10:20 UTC

Update Date

2022-08-31 06:44:51 UTC

Metabolite ID

MMDBc0019049

Metabolite Identification

Common Name

Brevicompanine B

Description

Brevicompanine B belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Brevicompanine B is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152111102D          

 30 33  0  0  1  0            999 V2000
    4.1864    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904   -0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3385    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5592    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0137    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0649    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.9373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -0.7077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  1  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21  6  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  6  0  0  0
 23 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 16 28  1  6  0  0  0
 17 29  1  1  0  0  0
 20 30  1  6  0  0  0
M  END


  Mrv1652305152111102D          

 30 33  0  0  1  0            999 V2000
    4.1864    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904   -0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3385    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5592    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0137    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0649    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.9373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -0.7077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  1  0  0  0
 17 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21  6  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  6  0  0  0
 23 16  1  0  0  0  0
 23 18  2  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 16 28  1  6  0  0  0
 17 29  1  1  0  0  0
 20 30  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019049

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12C[C@]3(C4=CC=CC=C4N[C@@]3([H])N1C(=O)[C@@]([H])(CC(C)C)N=C2O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H29N3O2/c1-6-21(4,5)22-12-17-18(26)23-16(11-13(2)3)19(27)25(17)20(22)24-15-10-8-7-9-14(15)22/h6-10,13,16-17,20,24H,1,11-12H2,2-5H3,(H,23,26)/t16-,17+,20+,22-/m1/s1

> <INCHI_KEY>
HAXPBJUEOMQIJN-HBCLNWRISA-N

> <FORMULA>
C22H29N3O2

> <MOLECULAR_WEIGHT>
367.493

> <EXACT_MASS>
367.225977186

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.25954111052773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,7S,9R)-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.949466329666667

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.167864483800447

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.812560944460725

> <JCHEM_PKA_STRONGEST_BASIC>
2.337804842479215

> <JCHEM_POLAR_SURFACE_AREA>
64.93

> <JCHEM_REFRACTIVITY>
106.67609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7S,9R)-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <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       7.815   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.616  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.741   0.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.232   3.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.020   2.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.280   4.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.119   1.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.409   0.265   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.664   2.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.244  -0.742   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.996  -1.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.848   2.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.451  -0.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.499   1.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.789  -0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.169  -0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.499   1.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.044   2.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.624  -0.742   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.316   0.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.626   2.861   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.971   1.467   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.121   1.275   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       5.440  -0.980   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.788   0.265   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0       0.754   3.795   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.913  -2.255   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       0.459  -1.750   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.662  -1.321   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   21                                                            
CONECT    5   21                                                            
CONECT    6    1   21                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    7   14                                                       
CONECT   10    8   15                                                       
CONECT   11   13   16                                                       
CONECT   12   17   22                                                       
CONECT   13    2    3   11                                                  
CONECT   14    9   15   22                                                  
CONECT   15   10   14   24                                                  
CONECT   16   11   19   23   28                                             
CONECT   17   12   18   25   29                                             
CONECT   18   17   23   26                                                  
CONECT   19   16   25   27                                                  
CONECT   20   22   24   25   30                                             
CONECT   21    4    5    6   22                                             
CONECT   22   12   14   20   21                                             
CONECT   23   16   18                                                       
CONECT   24   15   20                                                       
CONECT   25   17   19   20                                                  
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₂₉N₃O₂

Average Mass

367.493

Monoisotopic Mass

367.225977186

IUPAC Name

(1S,4R,7S,9R)-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

Traditional Name

(1S,4R,7S,9R)-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3(C4=CC=CC=C4N[C@@]3([H])N1C(=O)[C@@]([H])(CC(C)C)N=C2O)C(C)(C)C=C

InChI Identifier

InChI=1S/C22H29N3O2/c1-6-21(4,5)22-12-17-18(26)23-16(11-13(2)3)19(27)25(17)20(22)24-15-10-8-7-9-14(15)22/h6-10,13,16-17,20,24H,1,11-12H2,2-5H3,(H,23,26)/t16-,17+,20+,22-/m1/s1

InChI Key

HAXPBJUEOMQIJN-HBCLNWRISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen 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	0.11 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.95	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	2.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.68 m³·mol⁻¹	ChemAxon
Polarizability	41.26 Å³	ChemAxon
Number of Rings	4	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

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

8960513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10785200

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 Brevicompanine B (MMDBc0019049)

MOL for #<Metabolite:0x00007fed143ebfa8>

3D MOL for #<Metabolite:0x00007fed143ebfa8>

3D SDF for #<Metabolite:0x00007fed143ebfa8>

3D-SDF for #<Metabolite:0x00007fed143ebfa8>

PDB for #<Metabolite:0x00007fed143ebfa8>

3D PDB for #<Metabolite:0x00007fed143ebfa8>

SMILES for #<Metabolite:0x00007fed143ebfa8>

INCHI for #<Metabolite:0x00007fed143ebfa8>

Structure for #<Metabolite:0x00007fed143ebfa8>

3D Structure for #<Metabolite:0x00007fed143ebfa8>