MiMeDB: Showing metabocard for Ophiobolin C (MMDBc0057122)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-10-17 18:09:22 UTC

Update Date

2022-10-17 18:09:22 UTC

Metabolite ID

MMDBc0057122

Metabolite Identification

Common Name

Ophiobolin C

Description

4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. 4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171509522D          

 28 30  0  0  0  0            999 V2000
    0.2797   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -2.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3427   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1539   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4293   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2404   -1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8935   -1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -0.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -0.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -3.8919    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 12 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END


  Mrv1533004171509522D          

 28 30  0  0  0  0            999 V2000
    0.2797   -3.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -2.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3427   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1539   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4293   -1.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2404   -1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8935   -1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -0.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -0.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -1.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -2.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300   -0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -2.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -3.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5725   -3.8919    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 12 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057122

> <DATABASE_NAME>
MIME

> <SMILES>
CC(CCC=C(C)C)C1CCC2(C)CC3C(C(=O)CC3(C)O)C(C=O)=CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3

> <INCHI_KEY>
PLWMYIADTRHIMY-UHFFFAOYSA-N

> <FORMULA>
C25H38O3

> <MOLECULAR_WEIGHT>
386.576

> <EXACT_MASS>
386.282095084

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.92326133909518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde

> <ALOGPS_LOGP>
5.14

> <JCHEM_LOGP>
4.763664232333333

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.948073300675457

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.616880037993843

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98941536640931

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
115.51029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde

> <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       0.522  -5.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.008  -4.316   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.506  -4.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.506  -5.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.021  -4.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.535  -3.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.049  -3.193   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.534  -2.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.008  -3.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.649  -1.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.962  -0.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.133  -1.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.374  -0.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.556  -1.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.978  -1.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.568  -3.266   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.103  -3.145   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.103  -4.316   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.462  -1.647   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.149  -0.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.798   0.554   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.290   0.435   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.978  -4.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.556  -5.278   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.133  -4.688   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.543  -3.266   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.067  -5.777   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.669  -7.265   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9   12                                                  
CONECT   27   23   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Synonyms

Value	Source
3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al	MeSH

Molecular Formula

C₂₅H₃₈O₃

Average Mass

386.576

Monoisotopic Mass

386.282095084

IUPAC Name

4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde

Traditional Name

4-hydroxy-1,4-dimethyl-12-(6-methylhept-5-en-2-yl)-6-oxotricyclo[9.3.0.0³,⁷]tetradec-8-ene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)C1CCC2(C)CC3C(C(=O)CC3(C)O)C(C=O)=CCC12

InChI Identifier

InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3

InChI Key

PLWMYIADTRHIMY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Ophiobolane sesterterpenoids

Alternative Parents

Substituents

Ophiobolane sesterterpenoid
Tertiary alcohol
Cyclic alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	5.14	ALOGPS
logP	4.76	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.51 m³·mol⁻¹	ChemAxon
Polarizability	45.92 Å³	ChemAxon
Number of Rings	3	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

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

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

72762485

PDB ID

Not Available

ChEBI ID

Not Available

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 Ophiobolin C (MMDBc0057122)

MOL for #<Metabolite:0x00007fecf0517b80>

3D MOL for #<Metabolite:0x00007fecf0517b80>

3D SDF for #<Metabolite:0x00007fecf0517b80>

3D-SDF for #<Metabolite:0x00007fecf0517b80>

PDB for #<Metabolite:0x00007fecf0517b80>

3D PDB for #<Metabolite:0x00007fecf0517b80>

SMILES for #<Metabolite:0x00007fecf0517b80>

INCHI for #<Metabolite:0x00007fecf0517b80>

Structure for #<Metabolite:0x00007fecf0517b80>

3D Structure for #<Metabolite:0x00007fecf0517b80>