MiMeDB: Showing metabocard for Asterredione (MMDBc0019848)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:51:34 UTC

Update Date

2022-08-31 06:45:59 UTC

Metabolite ID

MMDBc0019848

Metabolite Identification

Common Name

Asterredione

Description

Asterredione belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Asterredione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181503252D          

 31 35  0  0  0  0            999 V2000
   -1.2910   -1.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -2.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1301   -1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439   -0.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038   -1.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770   -3.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233   -3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -2.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -2.9507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -4.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -4.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -5.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -5.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831   -5.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -5.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -4.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6556   -4.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -4.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4915   -3.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4915   -4.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 23 31  1  0  0  0  0
 26 31  1  0  0  0  0
M  END


  Mrv1533004181503252D          

 31 35  0  0  0  0            999 V2000
   -1.2910   -1.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -2.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1301   -1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439   -0.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3038   -1.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770   -3.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233   -3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -2.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -2.9507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -4.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -4.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -5.6121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -5.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831   -5.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -5.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -4.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6556   -4.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -4.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4915   -3.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4915   -4.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 23 31  1  0  0  0  0
 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019848

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)C1(C(=O)C(OC)=C(C1=O)C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H18N2O5/c1-30-20-19(15-11-25-17-9-5-3-7-13(15)17)21(27)24(22(20)28,23(29)31-2)16-12-26-18-10-6-4-8-14(16)18/h3-12,25-26H,1-2H3

> <INCHI_KEY>
XMAWYJWBFIGONN-UHFFFAOYSA-N

> <FORMULA>
C24H18N2O5

> <MOLECULAR_WEIGHT>
414.417

> <EXACT_MASS>
414.121571688

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
42.42200401888017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1,3-bis(1H-indol-3-yl)-4-methoxy-2,5-dioxocyclopent-3-ene-1-carboxylate

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.7640835716666667

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.771708599141537

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.407499360344072

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9619173868377064

> <JCHEM_POLAR_SURFACE_AREA>
101.25

> <JCHEM_REFRACTIVITY>
114.41010000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1,3-bis(1H-indol-3-yl)-4-methoxy-2,5-dioxocyclopent-3-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -2.410  -3.666   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.003  -4.292   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.243  -3.387   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.082  -1.855   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.156  -4.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.301  -3.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.317  -5.865   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.910  -6.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.880  -5.347   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.652  -5.508   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.590  -7.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.620  -9.142   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.850 -10.476   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.344 -10.156   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.902 -11.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.309 -10.435   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.470  -8.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.224  -7.998   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.183  -8.624   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.651  -6.635   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.651  -8.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   23                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   15                                                  
CONECT   21    8   22                                                       
CONECT   22   21                                                            
CONECT   23    5   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23   26                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₁₈N₂O₅

Average Mass

414.417

Monoisotopic Mass

414.121571688

IUPAC Name

methyl 1,3-bis(1H-indol-3-yl)-4-methoxy-2,5-dioxocyclopent-3-ene-1-carboxylate

Traditional Name

methyl 1,3-bis(1H-indol-3-yl)-4-methoxy-2,5-dioxocyclopent-3-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C(=O)C(OC)=C(C1=O)C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C24H18N2O5/c1-30-20-19(15-11-25-17-9-5-3-7-13(15)17)21(27)24(22(20)28,23(29)31-2)16-12-26-18-10-6-4-8-14(16)18/h3-12,25-26H,1-2H3

InChI Key

XMAWYJWBFIGONN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Methyl ester
Vinylogous ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
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	0.0028 g/L	ALOGPS
logP	3.73	ALOGPS
logP	3.76	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.25 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.41 m³·mol⁻¹	ChemAxon
Polarizability	42.42 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	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

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

11235347

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Asterredione (MMDBc0019848)

MOL for #<Metabolite:0x0000560be2702ad0>

3D MOL for #<Metabolite:0x0000560be2702ad0>

3D SDF for #<Metabolite:0x0000560be2702ad0>

3D-SDF for #<Metabolite:0x0000560be2702ad0>

PDB for #<Metabolite:0x0000560be2702ad0>

3D PDB for #<Metabolite:0x0000560be2702ad0>

SMILES for #<Metabolite:0x0000560be2702ad0>

INCHI for #<Metabolite:0x0000560be2702ad0>

Structure for #<Metabolite:0x0000560be2702ad0>

3D Structure for #<Metabolite:0x0000560be2702ad0>