MiMeDB: Showing metabocard for 5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone (MMDBc0004983)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:45:21 UTC

Update Date

2025-10-07 16:04:57 UTC

Metabolite ID

MMDBc0004983

Metabolite Identification

Common Name

5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone

Description

5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone is a benzoquinone, a class of organic compounds characterized by a six-membered aromatic ring with two ketone groups. This metabolite has been identified through advanced spectroscopic methods, including high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy, which confirmed its structure alongside other related compounds. The presence of the 3-oxo-1,2,2-trimethylcyclopentyl moiety suggests potential biological significance, as benzoquinones are known for their roles in various biochemical pathways, including redox reactions and as intermediates in the synthesis of more complex molecules. The specific metabolic pathways involving this compound may contribute to understanding its biological functions and potential applications in pharmacology or toxicology. The structural elucidation of 5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone highlights its relevance in the study of natural products and their derivatives, as evidenced by the findings reported in the literature (PMID:11014265 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100452D          

 18 19  0  0  1  0            999 V2000
    2.4530    5.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762    2.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    3.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071    3.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    4.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    4.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    5.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    3.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940    5.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039    3.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449    3.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8391    6.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8588    2.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  6  0  0  0
 15  6  1  0  0  0  0
 15 10  1  1  0  0  0
 15 14  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  2  0  0  0  0
 18 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004983

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC(=O)C(=CC1=O)[C@@]1(C)CCC(=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-9-7-12(17)10(8-11(9)16)15(4)6-5-13(18)14(15,2)3/h7-8H,5-6H2,1-4H3/t15-/m1/s1

> <INCHI_KEY>
FZLVOEBHJNRBTE-OAHLLOKOSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.322803963930575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-[(1S)-1,2,2-trimethyl-3-oxocyclopentyl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.192043953666667

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.572139996010122

> <JCHEM_PKA_STRONGEST_BASIC>
-7.365292909519871

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
70.48439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-[(1S)-1,2,2-trimethyl-3-oxocyclopentyl]cyclohexa-2,5-diene-1,4-dione

> <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       4.579  10.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.196   4.602   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.559   6.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.573   7.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.227   3.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.703   5.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.024   8.102   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.012   8.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.548   9.567   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.488   7.278   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.042   9.887   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.994   6.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.313   3.764   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.789   5.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.457   6.134   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.566  11.352   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.470   5.493   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.218   2.518   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7    9   12                                                       
CONECT    8   10   11                                                       
CONECT    9    1    7   11                                                  
CONECT   10    8   12   15                                                  
CONECT   11    8    9   16                                                  
CONECT   12    7   10   17                                                  
CONECT   13    5   14   18                                                  
CONECT   14    2    3   13   15                                             
CONECT   15    4    6   10   14                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

Synonyms

Value	Source
m-O-TMC-BQ	MeSH

Molecular Formula

C₁₅H₁₈O₃

Average Mass

246.306

Monoisotopic Mass

246.12559444

IUPAC Name

2-methyl-5-[(1S)-1,2,2-trimethyl-3-oxocyclopentyl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

2-methyl-5-[(1S)-1,2,2-trimethyl-3-oxocyclopentyl]cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C(=CC1=O)[C@@]1(C)CCC(=O)C1(C)C

InChI Identifier

InChI=1S/C15H18O3/c1-9-7-12(17)10(8-11(9)16)15(4)6-5-13(18)14(15,2)3/h7-8H,5-6H2,1-4H3/t15-/m1/s1

InChI Key

FZLVOEBHJNRBTE-OAHLLOKOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cuparane sesquiterpenoid
Sesquiterpenoid
Quinone
P-benzoquinone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.68	ALOGPS
logP	3.19	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	19.57	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.48 m³·mol⁻¹	ChemAxon
Polarizability	26.32 Å³	ChemAxon
Number of Rings	2	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

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species

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	Basidiomycota	3	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

9463054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11288067

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone (MMDBc0004983)

MOL for #<Metabolite:0x00007fb4d4692360>

3D MOL for #<Metabolite:0x00007fb4d4692360>

3D SDF for #<Metabolite:0x00007fb4d4692360>

3D-SDF for #<Metabolite:0x00007fb4d4692360>

PDB for #<Metabolite:0x00007fb4d4692360>

3D PDB for #<Metabolite:0x00007fb4d4692360>

SMILES for #<Metabolite:0x00007fb4d4692360>

INCHI for #<Metabolite:0x00007fb4d4692360>

Structure for #<Metabolite:0x00007fb4d4692360>

3D Structure for #<Metabolite:0x00007fb4d4692360>