MiMeDB: Showing metabocard for Roquefortine D (MMDBc0010523)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:40:28 UTC

Update Date

2022-08-31 06:31:50 UTC

Metabolite ID

MMDBc0010523

Metabolite Identification

Common Name

Roquefortine D

Description

6-hydroxy-4-[(1H-imidazol-5-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one 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. 6-hydroxy-4-[(1H-imidazol-5-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171508532D          

 29 33  0  0  0  0            999 V2000
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3524    0.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -0.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9655   -0.8674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
 12 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END


  Mrv1533004171508532D          

 29 33  0  0  0  0            999 V2000
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3524    0.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -0.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9655   -0.8674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
 12 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010523

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)(C=C)C12CC3N(C1NC1=CC=CC=C21)C(=O)C(CC1=CN=CN1)NC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-8,11-12,16-17,20,26H,1,9-10H2,2-3H3,(H,23,24)(H,25,28)

> <INCHI_KEY>
IQVNREJWRXOHEO-UHFFFAOYSA-N

> <FORMULA>
C22H25N5O2

> <MOLECULAR_WEIGHT>
391.475

> <EXACT_MASS>
391.200825065

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.22825711533379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1H-imidazol-5-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.1049080486666671

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.942937833737407

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.1655359986357

> <JCHEM_PKA_STRONGEST_BASIC>
6.743003336348254

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
110.04249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3H-imidazol-4-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.738  -0.739   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.185   0.735   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      13.724   0.766   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      14.230  -0.689   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      13.002  -1.619   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   10   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   12                                                  
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   20   28                                                       
CONECT   28   27    8   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₂₅N₅O₂

Average Mass

391.475

Monoisotopic Mass

391.200825065

IUPAC Name

4-[(1H-imidazol-5-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

4-(3H-imidazol-4-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C12CC3N(C1NC1=CC=CC=C21)C(=O)C(CC1=CN=CN1)NC3=O

InChI Identifier

InChI=1S/C22H25N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-8,11-12,16-17,20,26H,1,9-10H2,2-3H3,(H,23,24)(H,25,28)

InChI Key

IQVNREJWRXOHEO-UHFFFAOYSA-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
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Azole
Imidazole
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
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	0.13 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.17	ChemAxon
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.04 m³·mol⁻¹	ChemAxon
Polarizability	40.23 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

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	3	Human feces	Metabolic reconstruction

Exposure Sources

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15386782

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 Roquefortine D (MMDBc0010523)

MOL for #<Metabolite:0x00007fdae7fdc2c0>

3D MOL for #<Metabolite:0x00007fdae7fdc2c0>

3D SDF for #<Metabolite:0x00007fdae7fdc2c0>

3D-SDF for #<Metabolite:0x00007fdae7fdc2c0>

PDB for #<Metabolite:0x00007fdae7fdc2c0>

3D PDB for #<Metabolite:0x00007fdae7fdc2c0>

SMILES for #<Metabolite:0x00007fdae7fdc2c0>

INCHI for #<Metabolite:0x00007fdae7fdc2c0>

Structure for #<Metabolite:0x00007fdae7fdc2c0>

3D Structure for #<Metabolite:0x00007fdae7fdc2c0>