(-)-trans-Carveol (BioDeep_00000004185)

Secondary id: BioDeep_00000014767, BioDeep_00000017722, BioDeep_00000409666, BioDeep_00000638362, BioDeep_00000859687

human metabolite PANOMIX_OTCML-2023 Endogenous

代谢物信息卡片

(1S-trans)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol

化学式: C10H16O (152.12010859999998)
中文名称: (1R,5S)-rel-香芹醇, L-香芹醇,顺反异构体混合物, 香芹醇
谱图信息: 最多检出来源 Homo sapiens(natural_products) 3.85%

分子结构信息

SMILES: C=C(C)C1CC=C(C)C(O)C1
InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3

描述信息

Carveol is a natural terpenoid alcohol that is a constituent of spearmint oil. It has an odor and flavor that resemble those of spearmint and caraway. Consequently, it is used as a fragrance in cosmetics and as a flavor additive in the food industry.
Constituent of Valencia orange essence oil. Flavouring ingredient
Carveol is an endogenous metabolite.
Carveol is an endogenous metabolite.

同义名列表

15 个代谢物同义名

(1S-trans)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol; (1S,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol; (1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol; trans-5-(1-Methylethenyl)-2-methyl-2-cyclohexenol; (5R)-5-Isopropenyl-2-methyl-2-cyclohexen-1-ol; trans-Mentha-1,8-dien-6-ol; (-)-(4R,6S)-trans-Carveol; (-)-(4R,6S)-Carveol; (-)-trans-Carveol; (±)-trans-carveol; trans-(-)-Carveol; (1S,5R)-Carveol; trans-Carveol; (E)-carveol; Carveol

数据库引用编号

26 个数据库交叉引用编号

ChEBI: CHEBI:15389
ChEBI: CHEBI:23046
KEGG: C00964
PubChem: 94221
PubChem: 7438
HMDB: HMDB0003450
Metlin: METLIN6934
ChEMBL: CHEMBL1907992
ChEMBL: CHEMBL1385229
Wikipedia: Carveol
MetaCyc: CPD-10051
KNApSAcK: C00000814
foodb: FDB013717
chemspider: 85031
CAS: 20307-86-2
CAS: 2102-58-1
CAS: 1197-07-5
CAS: 99-48-9
PMhub: MS000015992
PubChem: 4215
LipidMAPS: LMPR0102090005
3DMET: B01361
NIKKAJI: J9.137E
RefMet: trans-Carveol
PubChem: 443178
medchemexpress: HY-W017370

分类词条

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)

PlantCyc(1)

(4R)-carvone biosynthesis: (-)-trans-carveol + NADP⁺ ⟶ (-)-carvone + H⁺ + NADPH

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

94 个相关的物种来源信息

282734 - Achillea erba-rotta: 10.1080/10412905.1989.9697751
282739 - Achillea grandifolia: 10.1055/S-2006-961401
282750 - Achillea moschata: 10.1080/10412905.1989.9697751
282752 - Achillea nana: 10.1080/10412905.1989.9697751
282753 - Achillea nobilis: 10.1080/10412905.1989.9697751
133233 - Achillea ptarmica: 10.1080/10412905.1989.9697751
68527 - Aegle marmelos: 10.1080/10412905.1995.9698520
39271 - Agastache rugosa: 10.1080/10412905.1992.9698139
501610 - Agathosma betulina: 10.1021/JF60201A021
925377 - Aloysia citrodora:
542672 - Aloysia triphylla:
518704 - Alpinia chinensis: 10.1080/10412905.1994.9698334
105671 - Alpinia conchigera: 10.1080/10412905.1995.9698499
94327 - Alpinia galanga: 10.1093/JISESA/IEU175
40922 - Anethum graveolens: 10.1021/JF00060A013
589713 - Anthemis aciphylla: 10.1248/CPB.54.222
262982 - Artemisia apiacea: 10.3389/FMICB.2014.00626
259893 - Artemisia argyi Lévl.et Vant.: -
496566 - Artemisia carvifolia: 10.3389/FMICB.2014.00626
72329 - Artemisia herba-alba: 10.1016/J.ARABJC.2012.04.042
401933 - Artemisia sericea: 10.1080/10412905.1999.9701070
4220 - Artemisia vulgaris: 10.1080/10412905.1992.9698101
72900 - Baccharis dracunculifolia: 10.1002/(SICI)1099-1026(199601)11:1<15::AID-FFJ541>3.0.CO;2-H
199392 - Baeckea frutescens: 10.1002/(SICI)1099-1026(1998070)13:4<245::AID-FFJ736>3.0.CO;2-J
41492 - Bellis perennis: 10.1016/0031-9422(95)00183-8
72904 - Boltonia asteroides: 10.1016/S0031-9422(00)89801-5
996322 - Cantinoa mutabilis: 10.1080/10412905.1995.9698469
77880 - Carapichea ipecacuanha: 10.5694/J.1326-5377.1998.TB126732.X
48032 - Carum carvi:
58030 - Chamaecyparis lawsoniana: 10.1080/10412905.1991.9697898
99808 - Chamaecyparis pisifera: 10.1080/10412905.1991.9697898
147000 - Chrysanthemum oreastrum: 10.3746/PNF.2012.17.3.234
558547 - Citrus deliciosa: 10.1002/HLCA.19630460506
79217 - Citrus iyo: 10.1271/BBB1961.47.1841
85571 - Citrus reticulata: 10.1002/HLCA.19630460506
260635 - Condea emoryi: 10.1021/NP50034A039
136216 - Curcuma kwangsiensis S.G.Lee et C.F.Liang: -
136218 - Curcuma phaeocaulis Val.: -
136221 - Curcuma wenyujin Y.H.Chen et C.Ling: -
66014 - Cymbopogon citratus: 10.1002/CBDV.201700436
79837 - Cymbopogon martinii: 10.1016/0305-1978(88)90091-9
325714 - Diplotaenia cachrydifolia: 10.1055/S-2006-962452
109117 - Echinophora tournefortii: 10.23893/1307-2080.APS.05611
586115 - Gaultheria mucronata: 10.1055/S-2007-969372
3635 - Gossypium hirsutum: 10.1021/JF60200A011
110723 - Hedychium spicatum: 10.1002/FFJ.2730100310
4232 - Helianthus annuus: 10.1021/JF00123A021
9606 - Homo sapiens:
9606 - Homo sapiens: -
646305 - Juniperus jaliscana: 10.1021/NP50040A037
119775 - Kippistia suaedifolia: 10.1016/0031-9422(82)83205-6
63011 - Laser trilobum:
39331 - Lavandula latifolia: 10.1016/0031-9422(83)85052-3
39333 - Lavandula stoechas: 10.1016/0305-1978(96)00023-3
145754 - Malva sylvestris: 10.1007/BF00629959
29780 - Mangifera indica: 10.1016/0031-9422(88)80124-9
21819 - Mentha: 10.1080/10412905.1992.9698144
292239 - Mentha arvensis: 10.1080/10412905.1990.9697828
29719 - Mentha spicata:
29719 - Mentha spicata: 10.1016/J.PHYTOCHEM.2006.04.025
1945650 - Micromeria maderensis: 10.1002/FFJ.2730100313
306398 - Micromeria sinaica: 10.3109/13880209109082877
1127086 - Mikania cordifolia: 10.1016/S0031-9422(00)80558-0
119949 - Myrtus communis:
268884 - Origanum majorana: 10.1055/S-2006-960024
1477654 - Pectis elongata var. floribunda: 10.1080/10412905.1999.9701062
253082 - Pelargonium quercifolium: 10.1080/10412905.1991.9697953
405322 - Piper cubeba: 10.1016/J.PHYTOCHEM.2006.04.025
13216 - Piper nigrum: 10.1021/JF60165A026
434234 - Pistacia atlantica: 10.1023/B:CONC.0000025459.72590.9E
33090 - Plants: -
174549 - Polygala senega: 10.1002/FFJ.2730100408
376575 - Renealmia floribunda: 10.1021/NP50035A037
313948 - Rhanterium epapposum: 10.1002/FFJ.2730020106
203015 - Rhodiola rosea: 10.1016/S0031-9422(02)00004-3
49605 - Rhododendron groenlandicum: 10.1007/BF00579758
1933764 - Salvia vermifolia: 10.1076/PHBI.40.1.67.5852
41644 - Santolina chamaecyparissus: 10.1002/FFJ.2730070109
169607 - Tagetes minuta: 10.1007/BF02536610
944772 - Tanacetum polycephalum: 10.1080/10412905.1999.9701194
1117157 - Teucrium polium: 10.1021/NP50039A032
1484035 - Thapsia maxima: 10.1080/10412905.1992.9698111
512635 - Thapsia villosa: 10.1080/10412905.1992.9698111
3317 - Thuja occidentalis: 10.1016/0305-1978(85)90081-X
3317 - Thuja occidentalis: 10.1080/10412905.1993.9698189
1205795 - Trachyspermum anethifolium: 10.1080/0972060X.2014.989187
945837 - Vaccinium ashei: 10.1111/J.1365-2621.1983.TB14849.X
69266 - Vaccinium corymbosum: 10.1111/J.1365-2621.1983.TB14849.X
1493660 - Vaccinium virgatum: 10.1111/J.1365-2621.1983.TB14849.X
29760 - Vitis vinifera: 10.3389/FMICB.2017.00457
1005655 - Xylopia aromatica: 10.1080/10412905.1993.9698250
1005659 - Xylopia sericea: 10.1021/NP50048A039
354530 - Zanthoxylum schinifolium: 10.1016/J.CHROMA.2005.10.032
136225 - Zingiber mioga: 10.1271/BBB1961.55.1655

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

Hyeonbin Kim, Mi Hee Kim, Ui-Lim Choi, Moonsoo Chung, Chul-Ho Yun, Youngkun Shim, Jaejun Oh, Sungbeom Lee, Gun Woong Lee. Molecular and Phenotypic Investigation on Antibacterial Activities of Limonene Isomers and Its Oxidation Derivative against Xanthomonas oryzae pv. Oryzae. Journal of microbiology and biotechnology. 2024 Jan; 34(3):1-10. doi: 10.4014/jmb.2311.11016. [PMID: 38247219]
Zhengyi Ling, Jingrui Li, Yanmei Dong, Wenying Zhang, Hongtong Bai, Shu Li, Su Wang, Hui Li, Lei Shi. Terpene produced by coexpression of the TPS and P450 genes from Lavandula angustifolia protects plants from herbivore attacks during budding stages. BMC plant biology. 2023 Oct; 23(1):477. doi: 10.1186/s12870-023-04490-7. [PMID: 37807036]
Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
Asmaa Jan Muhammad, Liangliang Hao, Lina Tariq Al Kury, Najeeb Ur Rehman, Arooj Mohsin Alvi, Haroon Badshah, Ikram Ullah, Fawad Ali Shah, Shupeng Li. Carveol Promotes Nrf2 Contribution in Depressive Disorders through an Anti-inflammatory Mechanism. Oxidative medicine and cellular longevity. 2022; 2022(?):4509204. doi: 10.1155/2022/4509204. [PMID: 35295720]
Arooj Mohsin Alvi, Lina Tariq Al Kury, Abdullah Alattar, Ikram Ullah, Asmaa Jan Muhammad, Reem Alshaman, Fawad Ali Shah, Arif Ullah Khan, Jinxing Feng, Shupeng Li. Carveol Attenuates Seizure Severity and Neuroinflammation in Pentylenetetrazole-Kindled Epileptic Rats by Regulating the Nrf2 Signaling Pathway. Oxidative medicine and cellular longevity. 2021; 2021(?):9966663. doi: 10.1155/2021/9966663. [PMID: 34422216]
Renata Evaristo Rodrigues da Silva, Andressa de Alencar Silva, Luís Pereira-de-Morais, Nayane de Sousa Almeida, Marcello Iriti, Marta Regina Kerntopf, Irwin Rose Alencar de Menezes, Henrique Douglas Melo Coutinho, Roseli Barbosa. Relaxant Effect of Monoterpene (-)-Carveol on Isolated Human Umbilical Cord Arteries and the Involvement of Ion Channels. Molecules (Basel, Switzerland). 2020 Jun; 25(11):. doi: 10.3390/molecules25112681. [PMID: 32527034]
Navneet Kaur, Khushminder Kaur Chahal, Amit Kumar, Ravinder Singh, Urvashi Bhardwaj. Antioxidant activity of Anethum graveolens L. essential oil constituents and their chemical analogues. Journal of food biochemistry. 2019 04; 43(4):e12782. doi: 10.1111/jfbc.12782. [PMID: 31353585]
Guo-Feng Mao, Xiao-Chang Mo, Hatem Fouad, Ghulam Abbas, Jian-Chu Mo. Attraction behaviour of Anagrus nilaparvatae to remote lemongrass (Cymbopogon distans) oil and its volatile compounds. Natural product research. 2018 Mar; 32(5):514-520. doi: 10.1080/14786419.2017.1326486. [PMID: 28503948]
Renilde Cordeiro de Souza, Mateus Matiuzzi da Costa, Bernardo Baldisserotto, Berta Maria Heinzmann, Denise Schmidt, Braulio Otomar Caron, Carlos Eduardo Copatti. Antimicrobial and synergistic activity of essential oils of Aloysia triphylla and Lippia alba against Aeromonas spp. Microbial pathogenesis. 2017 Dec; 113(?):29-33. doi: 10.1016/j.micpath.2017.10.013. [PMID: 29038058]
Lukas Schmidt, Thomas Göen. R-Limonene metabolism in humans and metabolite kinetics after oral administration. Archives of toxicology. 2017 Mar; 91(3):1175-1185. doi: 10.1007/s00204-016-1751-6. [PMID: 27325307]
Zheng Jiang, Hong Wang, Qi-nan Wu, Wei Yue, Da-wei Wu, Xiu-he Fan. [Qualitative and Quantitative Analysis of Major Constituents of Gland Products in Peltate Glandular Trichomes of Schizonepetae Spica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jan; 39(1):31-6. doi: ". [PMID: 30079698]
Hana Moon, Min Jung Kim, Hee Jin Son, Hae-Jin Kweon, Jung Tae Kim, Yiseul Kim, Jaewon Shim, Byung-Chang Suh, Mee-Ra Rhyu. Five hTRPA1 Agonists Found in Indigenous Korean Mint, Agastache rugosa. PloS one. 2015; 10(5):e0127060. doi: 10.1371/journal.pone.0127060. [PMID: 25978436]
M Govindarajan, R Sivakumar, M Rajeswari, K Yogalakshmi. Chemical composition and larvicidal activity of essential oil from Mentha spicata (Linn.) against three mosquito species. Parasitology research. 2012 May; 110(5):2023-32. doi: 10.1007/s00436-011-2731-7. [PMID: 22139403]
Tomoko Iizuka, Yasuhiro Nishikawa, Yoshihiro Mori, Natsuko Zenimura, Takuyuki Matsumoto, Katsutoshi Hiramatsu, Masahiro Komiya. Artist® tablets (carvedilol) for hypertensive patients in Japan: results of a long-term special survey. Drugs in R&D. 2011; 11(2):191-205. doi: 10.2165/11592460-000000000-00000. [PMID: 21679008]
Devin R Polichuk, Yansheng Zhang, Darwin W Reed, Janice F Schmidt, Patrick S Covello. A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua. Phytochemistry. 2010 Aug; 71(11-12):1264-9. doi: 10.1016/j.phytochem.2010.04.026. [PMID: 20621795]
S Jana, G S Shekhawat. Anethum graveolens: An Indian traditional medicinal herb and spice. Pharmacognosy reviews. 2010 Jul; 4(8):179-84. doi: 10.4103/0973-7847.70915. [PMID: 22228959]
Peng Wang, Chui Hua Kong, Chao Xian Zhang. Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L. Molecules (Basel, Switzerland). 2006 Jul; 11(7):549-55. doi: 10.3390/11070549. [PMID: 17971726]
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]
Vijai K Agnihotri, Rajendra K Thappa, Baleshwar Meena, Bal K Kapahi, Rajendra K Saxena, Ghulam N Qazi, Shri G Agarwal. Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India). Phytochemistry. 2004 Aug; 65(16):2411-3. doi: 10.1016/j.phytochem.2004.07.004. [PMID: 15381015]
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]
Sarah A Holstein, Raymond J Hohl. Monoterpene regulation of Ras and Ras-related protein expression. Journal of lipid research. 2003 Jun; 44(6):1209-15. doi: 10.1194/jlr.m300057-jlr200. [PMID: 12671036]
Hossein Hosseinzadeh, Gholam Reza Karimi, Maryam Ameri. Effects of Anethum graveolens L. seed extracts on experimental gastric irritation models in mice. BMC pharmacology. 2002 Dec; 2(?):21. doi: 10.1186/1471-2210-2-21. [PMID: 12493079]
Katumi Umano, Yukio Hagi, Takayuki Shibamoto. Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.). Journal of agricultural and food chemistry. 2002 Sep; 50(19):5355-9. doi: 10.1021/jf0203951. [PMID: 12207474]
Matthias Wüst, Rodney B Croteau. Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. Biochemistry. 2002 Feb; 41(6):1820-7. doi: 10.1021/bi011717h. [PMID: 11827526]
M Wüst, D B Little, M Schalk, R Croteau. Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites. Archives of biochemistry and biophysics. 2001 Mar; 387(1):125-36. doi: 10.1006/abbi.2000.2248. [PMID: 11368174]
M D Green, D J Clarke, E M Oturu, P B Styczynski, M R Jackson, B Burchell, T R Tephly. Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols. Archives of biochemistry and biophysics. 1995 Oct; 322(2):460-8. doi: 10.1006/abbi.1995.1489. [PMID: 7574722]
E W Watt, J Wiley, G F Fletcher. Effect of dietary control and exercise training on daily food intake and serum lipids in postmyocardial infarction patients. The American journal of clinical nutrition. 1976 Aug; 29(8):900-4. doi: 10.1093/ajcn/29.8.900. [PMID: 181978]
J Ditzel. Oxygen transport impairment in diabetes. Diabetes. 1976; 25(2 SUPPL):832-8. doi: . [PMID: 9322]