MiMeDB: Showing metabocard for 3-oxochola-4,6-dien-24-oic acid (MMDBc0055412)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:51:27 UTC

Update Date

2022-08-12 20:09:22 UTC

Metabolite ID

MMDBc0055412

Metabolite Identification

Common Name

3-oxochola-4,6-dien-24-oic acid

Description

3-oxochola-4,6-dien-24-oate belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. Based on a literature review very few articles have been published on 3-oxochola-4,6-dien-24-oate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221512D          

 32 35  0  0  1  0            999 V2000
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642    3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1750    3.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687    4.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    3.9104    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 15  1  1  6  0  0  0
 15  4  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  6  0  0  0
 20  8  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23  2  1  6  0  0  0
 23 12  1  0  0  0  0
 23 16  1  0  0  0  0
 23 21  1  0  0  0  0
 24  3  1  6  0  0  0
 24 13  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
 25 17  2  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 15 28  1  1  0  0  0
 18 29  1  6  0  0  0
 19 30  1  1  0  0  0
 20 31  1  1  0  0  0
 21 32  1  1  0  0  0
M  CHG  1  27  -1
M  END


  Mrv1652306172221512D          

 32 35  0  0  1  0            999 V2000
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642    3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1750    3.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687    4.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    3.9104    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5533    2.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 15  1  1  6  0  0  0
 15  4  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  6  0  0  0
 20  8  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23  2  1  6  0  0  0
 23 12  1  0  0  0  0
 23 16  1  0  0  0  0
 23 21  1  0  0  0  0
 24  3  1  6  0  0  0
 24 13  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
 25 17  2  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 15 28  1  1  0  0  0
 18 29  1  6  0  0  0
 19 30  1  1  0  0  0
 20 31  1  1  0  0  0
 21 32  1  1  0  0  0
M  CHG  1  27  -1
M  END
> <DATABASE_ID>
MMDBc0055412

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(CCC([O-])=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C=CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/p-1/t15-,18+,19-,20+,21+,23+,24-/m1/s1

> <INCHI_KEY>
CREVIXFSUWYGRJ-IHMUCKAYSA-M

> <FORMULA>
C24H33O3

> <MOLECULAR_WEIGHT>
369.526

> <EXACT_MASS>
369.243518503

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.50872678992071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoate

> <JCHEM_LOGP>
4.821815130666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.93862862085184

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.811890890639279

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7738289358314105

> <JCHEM_POLAR_SURFACE_AREA>
57.199999999999996

> <JCHEM_REFRACTIVITY>
119.43359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.613   5.662   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.193   7.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.248   8.305   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.719   7.299   0.000  0.00  0.00           O-1
HETATM   28  H   UNK     0       1.033   4.236   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.509  -1.043   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.411   1.514   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.017  -0.136   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    9   15                                                       
CONECT    5    6   16                                                       
CONECT    6    5   18                                                       
CONECT    7    8   19                                                       
CONECT    8    7   20                                                       
CONECT    9    4   22                                                       
CONECT   10   12   17                                                       
CONECT   11   13   21                                                       
CONECT   12   10   23                                                       
CONECT   13   11   24                                                       
CONECT   14   16   17                                                       
CONECT   15    1    4   19   28                                             
CONECT   16    5   14   23                                                  
CONECT   17   10   14   25                                                  
CONECT   18    6   20   21   29                                             
CONECT   19    7   15   24   30                                             
CONECT   20    8   18   24   31                                             
CONECT   21   11   18   23   32                                             
CONECT   22    9   26   27                                                  
CONECT   23    2   12   16   21                                             
CONECT   24    3   13   19   20                                             
CONECT   25   17                                                            
CONECT   26   22                                                            
CONECT   27   22                                                            
CONECT   28   15                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   20                                                            
CONECT   32   21                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Value	Source
3-Oxochola-4,6-dien-24-Oic acid	Generator

Molecular Formula

C₂₄H₃₃O₃

Average Mass

369.526

Monoisotopic Mass

369.243518503

IUPAC Name

(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoate

Traditional Name

(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-14-yl]pentanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CCC([O-])=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C=CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

InChI Identifier

InChI=1S/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/p-1/t15-,18+,19-,20+,21+,23+,24-/m1/s1

InChI Key

CREVIXFSUWYGRJ-IHMUCKAYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Bile acids, alcohols and derivatives

Alternative Parents

Substituents

Bile acid, alcohol, or derivatives
3-oxosteroid
Oxosteroid
Cyclohexenone
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic anion
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	4.82	ChemAxon
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	119.43 m³·mol⁻¹	ChemAxon
Polarizability	43.51 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

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
Bacteria	Firmicutes	1	Human ; Human feces

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

20171404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20848979

PDB ID

Not Available

ChEBI ID

87748

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 3-oxochola-4,6-dien-24-oic acid (MMDBc0055412)

MOL for #<Metabolite:0x00007fed15c0bdb8>

3D MOL for #<Metabolite:0x00007fed15c0bdb8>

3D SDF for #<Metabolite:0x00007fed15c0bdb8>

3D-SDF for #<Metabolite:0x00007fed15c0bdb8>

PDB for #<Metabolite:0x00007fed15c0bdb8>

3D PDB for #<Metabolite:0x00007fed15c0bdb8>

SMILES for #<Metabolite:0x00007fed15c0bdb8>

INCHI for #<Metabolite:0x00007fed15c0bdb8>

Structure for #<Metabolite:0x00007fed15c0bdb8>

3D Structure for #<Metabolite:0x00007fed15c0bdb8>