(R)-Carvone (BioDeep_00000001097)
Secondary id: BioDeep_00000271384, BioDeep_00000410682
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C10H14O (150.1045)
中文名称: 左旋香芹酮, （-）-香芹酮
谱图信息:
最多检出来源 Viridiplantae(plant) 20.43%
分子结构信息
SMILES: C=C(C)[C@@H]1CC=C(C)C(=O)C1
InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
描述信息
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 a volatile terpenoid found in cannabis plants (PMID:6991645 ). 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).
(-)-carvone is a carvone having (R) configuration. It is an enantiomer of a (+)-carvone.
(-)-Carvone is a natural product found in Poiretia latifolia, Licaria triandra, and other organisms with data available.
See also: Myrrh (part of); Spearmint Oil (part of).
Constituent of spearmint (Mentha crispa) costmary, kuromoji and other oils. Flavouring ingredient
A carvone having (R) configuration.
(-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].
(-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].
(-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].
(-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].
同义名列表
60 个代谢物同义名
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (theta)-; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)-; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-; (-)-Carvone, primary pharmaceutical reference standard; (5R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one; (R)-2-METHYL-5-(1- METHYLETHENYL)-2-CYCLOHEXEN-1-ONE; (R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one; 2-Methyl-5-(1-methylethenyl)-(R)-2-Cyclohexen-1-one; (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; (R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; (R)-5-Isopropenyl-2-methyl-2-cyclohexenone, Carvol; (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one; (R)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; (5R)-5-isopropenyl-2-methyl-cyclohex-2-en-1-one; (R)-5-isopropenyl-2-methylcyclohex-2-en-1-one; l-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; (R)-5-Isopropenyl-2-methyl-2-cyclohexenone; (R)-CARVONE (CONSTITUENT OF MYRRH) [DSC]; (R)-CARVONE (CONSTITUENT OF MYRRH); p-Mentha-6,8-dien-2-one, (R)-(-)-; (-)-Carvone, analytical standard; (R)-(-)- P-MENTHA-6,8-DIEN-2-ONE; (4R)-p-mentha-1(6),8-dien-2-one; (R)-(-)-p-Mentha-6,8-dien-2-one; p-Mentha-6,8-dien-2-one, (-)-; L-Carvone, natural, 99\\%, FG; l-p-Mentha-1(6),8-dien-2-one; (-)-p-Mentha-6,8-dien-2-one; l-6,8(9)-p-Menthadien-2-one; (R)-p-mentha-6,8-dien-2-one; L-Carvone, >=97\\%, FCC, FG; (R)-(-)-Carvone, 98\\%; l-Carvone (natural); CARVONE L-FORM [MI]; (-)-CARVONE [FCC]; (4R)-(-)-Carvone; (-)-(4R)-carvone; (R)-(-)-Carvone; (-)-(R)-Carvone; UNII-5TO7X34D3D; CARVONE L-FORM; CARVONE [FHFI]; Carvone, (-)-; R-(-)-Carvone; L(-)-Carvone; Tox21_300931; (4R)-Carvone; Levo-carvone; CARVONE, L-; (R)-Carvone; (+) Carvone; (-)-Carvone; 5TO7X34D3D; AI3-36200; l-Carvone; r-carvone; Carvol; 07V; (-)-Carvone; (-)-Carvone
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:15400
- KEGG: C01767
- KEGGdrug: D70933
- PubChem: 439570
- HMDB: HMDB0035089
- Metlin: METLIN41072
- ChEMBL: CHEMBL2229268
- LipidMAPS: LMPR0102090007
- ChemIDplus: 0006485401
- KNApSAcK: C00000807
- foodb: FDB013718
- chemspider: 388655
- CAS: 6485-40-1
- medchemexpress: HY-W017423
- MetaboLights: MTBLC15400
- PubChem: 4900
- PDB-CCD: 07V
- 3DMET: B01496
- NIKKAJI: J15.688D
- KNApSAcK: 15400
- LOTUS: LTS0223461
- wikidata: Q27089417
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
3 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(2)
- (4R)-carveol and (4R)-dihydrocarveol degradation:
(-)-cis-carveol + oxidized DCPIP ⟶ (-)-carvone + H+ + reduced DCPIP - (4R)-carvone biosynthesis:
geranyl diphosphate ⟶ (4S)-limonene + diphosphate
WikiPathways(0)
Plant Reactome(0)
INOH(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
26 个相关的物种来源信息
- 40922 - Anethum graveolens: 10.1021/JF00060A013
- 246351 - Canarium zeylanicum: 10.1016/S0031-9422(00)81969-X
- 3483 - Cannabis sativa: 10.1055/S-0028-1097617
- 48032 - Carum carvi: 10.1021/JF00060A013
- 260635 - Condea emoryi: 10.1021/NP50034A039
- 34317 - Eucalyptus globulus: 10.1002/CBER.19470800611
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 5314 - Ganoderma: -
- 5315 - Ganoderma lucidum: 10.1016/J.PHYTOCHEM.2005.10.025
- 9606 - Homo sapiens: -
- 71060 - Isocoma pluriflora: 10.1021/NP50001A004
- 128638 - Licaria triandra: 10.1002/JPS.3030390406
- 85864 - Magnolia Officinalis Rehd Et Wils\uff0e: -
- 883867 - Matricaria discoidea: 10.1016/S0031-9422(00)97295-9
- 56017 - Matricaria matricarioides: 10.1016/S0031-9422(00)97295-9
- 292239 - Mentha arvensis: 10.1002/JPS.3030380504
- 294736 - Mentha diemenica: 10.1002/JPS.3030380504
- 29719 - Mentha spicata:
- 48386 - Perilla Frutescens: -
- 3329 - Picea abies: 10.1055/S-0028-1097609
- 33090 - Plants: -
- 1192317 - Poiretia latifolia: 10.1590/S0103-50532010000500003
- 694343 - Pseudodictamnus undulatus: 10.1002/MRC.2050
- 49605 - Rhododendron groenlandicum: 10.1007/BF00579758
- 2878271 - Thymus camphoratus: 10.1016/S0031-9422(97)00117-9
- 94328 - Zingiber Officinale Roscoe: -
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- V Y Hatano, A S Torricelli, A C C Giassi, L A Coslope, M B Viana. Anxiolytic effects of repeated treatment with an essential oil from Lippia alba and (R)-(-)-carvone in the elevated T-maze.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2012 Mar; 45(3):238-43. doi:
10.1590/s0100-879x2012007500021. [PMID: 22358424] - Karina Caballero-Gallardo, Jesús Olivero-Verbel, Elena E Stashenko. Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
Journal of agricultural and food chemistry.
2011 Mar; 59(5):1690-6. doi:
10.1021/jf103937p. [PMID: 21291237] - Rui Fang, Cai Hong Jiang, Xiu Yi Wang, Hai Ming Zhang, Zhi Long Liu, Ligang Zhou, Shu Shan Du, Zhi Wei Deng. Insecticidal activity of essential oil of Carum Carvi fruits from China and its main components against two grain storage insects.
Molecules (Basel, Switzerland).
2010 Dec; 15(12):9391-402. doi:
10.3390/molecules15129391. [PMID: 21173724] - Nikoletta G Ntalli, Federico Ferrari, Ioannis Giannakou, Urania Menkissoglu-Spiroudi. Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
Journal of agricultural and food chemistry.
2010 Jul; 58(13):7856-63. doi:
10.1021/jf100797m. [PMID: 20527965] - Tim G Elford, Dennis G Hall. Total synthesis of (+)-chinensiolide B via tandem allylboration/lactonization.
Journal of the American Chemical Society.
2010 Feb; 132(5):1488-9. doi:
10.1021/ja9104478. [PMID: 20067261] - J R-M Brown, I P Thompson, G I Paton, A C Singer. Enhanced biotransformation of TCE using plant terpenoids in contaminated groundwater.
Letters in applied microbiology.
2009 Dec; 49(6):769-74. doi:
10.1111/j.1472-765x.2009.02738.x. [PMID: 19843209] - Brent Tisserat, Mark Berhow, Steven F Vaughn. Spearmint plantlet culture system as a means to study secondary metabolism.
Methods in molecular biology (Clifton, N.J.).
2009; 547(?):313-24. doi:
10.1007/978-1-60327-287-2_25. [PMID: 19521855] - Damião P de Sousa, Genival A S Júnior, Luciana N Andrade, Flávia R Calasans, Xirley P Nunes, José M Barbosa-Filho, Josemar S Batista. Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2008 Nov; 63(11-12):808-12. doi:
10.1515/znc-2008-11-1205. [PMID: 19227827] - Juan Carlos Ramos Gonçalves, Fernando de Sousa Oliveira, Rubens Batista Benedito, Damião Pergentino de Sousa, Reinaldo Nóbrega de Almeida, Demetrius Antônio Machado de Araújo. Antinociceptive activity of (-)-carvone: evidence of association with decreased peripheral nerve excitability.
Biological & pharmaceutical bulletin.
2008 May; 31(5):1017-20. doi:
10.1248/bpb.31.1017. [PMID: 18451538] - Rob W H M van Tol, Henk J Swarts, Anton van der Linden, J H Visser. Repellence of the red bud borer Resseliella oculiperda from grafted apple trees by impregnation of rubber budding strips with essential oils.
Pest management science.
2007 May; 63(5):483-90. doi:
10.1002/ps.1374. [PMID: 17421054] - Wayne L Silver, Tod R Clapp, Leslie M Stone, Sue C Kinnamon. TRPV1 receptors and nasal trigeminal chemesthesis.
Chemical senses.
2006 Nov; 31(9):807-12. doi:
10.1093/chemse/bjl022. [PMID: 16908491] - Kerry L Ringer, Edward M Davis, Rodney Croteau. Monoterpene metabolism. Cloning, expression, and characterization of (-)-isopiperitenol/(-)-carveol dehydrogenase of peppermint and spearmint.
Plant physiology.
2005 Mar; 137(3):863-72. doi:
10.1104/pp.104.053298. [PMID: 15734920] - Tom W Pope, Colin A M Campbell, Jim Hardie, Lester J Wadhams. Electroantennogram responses of the three migratory forms of the damson-hop aphid, Phorodon humuli, to aphid pheromones and plant volatiles.
Journal of insect physiology.
2004 Nov; 50(11):1083-92. doi:
10.1016/j.jinsphys.2004.09.010. [PMID: 15607511] - Fatih Demirci, Yoshiaki Noma, Neş'e Kirimer, K Hüsnü Can Başer. Microbial transformation of (-)-carvone.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2004 May; 59(5-6):389-92. doi:
". [PMID: 18998407] - Ora A Carter, Reuben J Peters, Rodney Croteau. Monoterpene biosynthesis pathway construction in Escherichia coli.
Phytochemistry.
2003 Sep; 64(2):425-33. doi:
10.1016/s0031-9422(03)00204-8. [PMID: 12943759] - A Srikrishna, K Anebouselvy. An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes.
The Journal of organic chemistry.
2001 Oct; 66(21):7102-6. doi:
10.1021/jo0105484. [PMID: 11597236] - W Jäger, M Mayer, G Reznicek, G Buchbauer. Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels.
The Journal of pharmacy and pharmacology.
2001 May; 53(5):637-42. doi:
10.1211/0022357011775965. [PMID: 11370703] - L Y Mou, L Y Zhu, Z Y Lin, X T Liang. Stereoselective total synthesis of chrysanthemol.
Journal of Asian natural products research.
2001; 3(2):103-16. doi:
10.1080/10286020108041377. [PMID: 11407809] - F Demirci, N Kirimer, B Demirci, Y Noma, K H Başer. Screening of biotransformation products of carvone enantiomers by headspace-SPME/GC-MS.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2001 Jan; 56(1-2):58-64. doi:
10.1515/znc-2001-1-211. [PMID: 11302215]
