MiMeDB: Showing metabocard for D-Carvone (MMDBc0047677)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:37:24 UTC

Update Date

2024-10-06 19:14:52 UTC

Metabolite ID

MMDBc0047677

Metabolite Identification

Common Name

D-Carvone

Description

Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817 ). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904 ) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792 ) and patients with epilepsy (PMID:31239862 ). It also has been successfully used as a biopesticide (PMID:30250476 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(4S)-Carvone	ChEBI
(+)-(S)-Carvone	ChEBI
(5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one	ChEBI
(S)-(+)-Carvone	ChEBI
(S)-(+)-p-Mentha-6,8-dien-2-one	ChEBI
(S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one	ChEBI
(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one	ChEBI
(S)-5-Isopropenyl-2-methylcyclohex-2-en-1-one	ChEBI
Carvol	ChEBI
Carvone	ChEBI
D-(+)-Carvone	ChEBI
D-Carvone	ChEBI
(+)-Carvone	Kegg
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one	HMDB
D-p-Mentha-6,8(9)-dien-2-one	HMDB
(S)-Carvone	ChEBI

Molecular Formula

C₁₀H₁₄O

Average Mass

150.2176

Monoisotopic Mass

150.10446507

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1

InChI Key

ULDHMXUKGWMISQ-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carvone (CHEBI:15399 )
Menthane monoterpenoids (C11383 )
Cyclic monoterpenes (C11383 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Saliva
Urine

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Actinobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0004487

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16724

PDB ID

Not Available

ChEBI ID

15399

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]
Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. doi: 10.1006/jtbi.1994.1057. [PubMed:8207942 ]
Jager W, Mayer M, Reznicek G, Buchbauer G: Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. J Pharm Pharmacol. 2001 May;53(5):637-42. doi: 10.1211/0022357011775965. [PubMed:11370703 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
McHugh D, Hu SS, Rimmerman N, Juknat A, Vogel Z, Walker JM, Bradshaw HB: N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC Neurosci. 2010 Mar 26;11:44. doi: 10.1186/1471-2202-11-44. [PubMed:20346144 ]
Tauber S, Paulsen K, Wolf S, Synwoldt P, Pahl A, Schneider-Stock R, Ullrich O: Regulation of MMP-9 by a WIN-binding site in the monocyte-macrophage system independent from cannabinoid receptors. PLoS One. 2012;7(11):e48272. doi: 10.1371/journal.pone.0048272. Epub 2012 Nov 6. [PubMed:23139770 ]
Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF: N-Arachidonoyl glycine suppresses Na(+)/Ca(2)(+) exchanger-mediated Ca(2)(+) entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. [PubMed:23517055 ]
de Groot AC, Schmidt E: Essential Oils, Part III: Chemical Composition. Dermatitis. 2016 Jul-Aug;27(4):161-9. doi: 10.1097/DER.0000000000000193. [PubMed:27427817 ]
Mollazadeh H, Afshari AR, Hosseinzadeh H: Review on the Potential Therapeutic Roles of Nigella sativa in the Treatment of Patients with Cancer: Involvement of Apoptosis: - Black cumin and cancer. J Pharmacopuncture. 2017 Sep;20(3):158-172. doi: 10.3831/KPI.2017.20.019. Epub 2017 Sep 30. [PubMed:30087792 ]
Singh P, Pandey AK: Prospective of Essential Oils of the Genus Mentha as Biopesticides: A Review. Front Plant Sci. 2018 Sep 10;9:1295. doi: 10.3389/fpls.2018.01295. eCollection 2018. [PubMed:30250476 ]
Mahboubi M: Caraway as Important Medicinal Plants in Management of Diseases. Nat Prod Bioprospect. 2019 Jan;9(1):1-11. doi: 10.1007/s13659-018-0190-x. Epub 2018 Oct 29. [PubMed:30374904 ]
Bahr TA, Rodriguez D, Beaumont C, Allred K: The Effects of Various Essential Oils on Epilepsy and Acute Seizure: A Systematic Review. Evid Based Complement Alternat Med. 2019 May 22;2019:6216745. doi: 10.1155/2019/6216745. eCollection 2019. [PubMed:31239862 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for D-Carvone (MMDBc0047677)

MOL for #<Metabolite:0x00007f4704e8d0a8>

3D MOL for #<Metabolite:0x00007f4704e8d0a8>

3D SDF for #<Metabolite:0x00007f4704e8d0a8>

3D-SDF for #<Metabolite:0x00007f4704e8d0a8>

PDB for #<Metabolite:0x00007f4704e8d0a8>

3D PDB for #<Metabolite:0x00007f4704e8d0a8>

SMILES for #<Metabolite:0x00007f4704e8d0a8>

INCHI for #<Metabolite:0x00007f4704e8d0a8>

Structure for #<Metabolite:0x00007f4704e8d0a8>

3D Structure for #<Metabolite:0x00007f4704e8d0a8>