Euphol (BioDeep_00000000541)

human metabolite PANOMIX_OTCML-2023 Endogenous

代谢物信息卡片

(3S,5R,10S,13S,14S)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C30H50O (426.386145)
中文名称: 大戟二烯醇, 乙草胺醇, 大戟二烯醇
谱图信息: 最多检出来源 Viridiplantae(plant) 1.69%

分子结构信息

SMILES: C1C[C@]2(C)C3CC[C@@]4(C)[C@H]([C@]([H])(C)CC/C=C(\C)/C)CC[C@]4(C)C=3CC[C@@]2([H])C(C)(C)[C@H]1O
InChI: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1

描述信息

Euphol is a triterpenoid.
Euphol is a natural product found in Euphorbia nicaeensis, Euphorbia boetica, and other organisms with data available.
Constituent of Euphorbia subspecies (CCD). Euphol is found in many foods, some of which are cucumber, soy bean, shea tree, and tea.
Euphol is found in cucumber. Euphol is a constituent of Euphorbia species (CCD)
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].

同义名列表

17 个代谢物同义名

(3S,5R,10S,13S,14S)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5R,10S,13S,14S,17S)-17-[(1R)-1,5-dimethylhex-4-enyl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol; Lanosta-8,24-dien-3-ol, (3.beta.,13.alpha.,14.beta.,17.alpha.)-; 13alpha,14beta,17betaH-Lanosta-8,24-dien-3beta-ol (8CI); (3beta,13alpha,14beta,17alpha)-Lanosta-8,24-dien-3-ol; Lanosta-8,24-dien-3-ol,(3b,13a,14b,17a)-; (20R)-(+)-triucalla-8,24-diene-3beta-ol; 5alpha-Eupha-8,24-dien-3beta-ol; 8,24-euphadien-3 beta-ol; Eupha-8,24-dienol; (+)-alpha-Euphol; Euphol (6CI); alpha-Euphol; Euphadienol; (+)-Euphol; (s)-euphol; euphol

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:4940
KEGG: C08624
PubChem: 441678
HMDB: HMDB0031438
Metlin: METLIN53769
ChEMBL: CHEMBL465181
LipidMAPS: LMPR0106090002
MeSH: euphol
KNApSAcK: C00003745
foodb: FDB004483
chemspider: 390292
CAS: 514-47-6
medchemexpress: HY-N0313
PubChem: 10817
3DMET: B02278
NIKKAJI: J14.838E

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

83 个相关的物种来源信息

211701 Clusia columnaris: 10.1590/S0102-695X2008000100003
489341 Monocyclanthus vignei: 10.1016/0031-9422(92)80456-O
142860 Euphorbia tirucalli:
1129975 Euphorbia caducifolia: 10.1016/S0031-9422(00)97902-0
3888 Pisum sativum: 10.1016/S0031-9422(00)94844-1
3827 Cicer arietinum: 10.1016/S0031-9422(00)94844-1
3864 Lens culinaris: 10.1016/S0031-9422(00)94844-1
3860 Lathyrus sativus: 10.1016/S0031-9422(00)94844-1
3847 Glycine max: 10.1016/S0031-9422(00)94844-1
3821 Cajanus cajan: 10.1016/S0031-9422(00)94844-1
1091639 Euphorbia oxyphylla: 10.1016/S0031-9422(00)82286-4
3659 Cucumis sativus: 10.1016/0031-9422(82)85222-9
3656 Cucumis melo: 10.1016/0031-9422(82)85222-9
292385 Vitellaria paradoxa: 10.1007/BF02534064
4442 Camellia sinensis: 10.1007/BF02534064
4443 Camellia japonica:
3527 Phytolacca americana: 10.1007/BF02534064
385388 Camellia oleifera:
182300 Camellia sasanqua:
457243 Euphorbia cotinifolia: 10.1016/S0031-9422(00)85859-8
1492770 Euphorbia trigona: 10.1016/0031-9422(88)83136-4
1138358 Euphorbia portulacoides: 10.1016/0031-9422(95)00752-0
212925 Euphorbia lathyris:
239687 Euphorbia kansui:
334664 Euphorbia antiquorum:
1591303 Dacryodes hopkinsii: 10.1590/S0103-50532004000300008
156472 Clusia multiflora: 10.1016/0031-9422(94)00642-7
457265 Euphorbia resinifera: 10.1016/J.PHYTOCHEM.2008.01.004
1281384 Euphorbia sapinii: 10.1016/J.PHYTOL.2011.04.001
316813 Euphorbia abyssinica: 10.1016/S0031-9422(97)01065-0
1333886 Euphorbia aleppica: 10.1016/0031-9422(95)00361-A
1087772 Euphorbia nicaeensis: 10.1055/S-2006-959736
212879 Euphorbia drupifera: 10.1016/J.FITOTE.2007.02.002
457253 Euphorbia jolkinii: 10.1002/HLCA.200890230
1091645 Euphorbia retusa: 10.1016/0031-9422(73)80529-1
1091647 Euphorbia sulcata: 10.1016/0031-9422(73)80529-1
758543 Euphorbia condylocarpa: 10.1007/BF00564277
1091613 Euphorbia boetica: 10.1021/NP50116A020
334689 Euphorbia neriifolia: 10.1080/1057563031000122068
1534498 Euphorbia fusiformis: 10.1055/S-2006-962079
211701 Clusia columnaris: 10.1590/S0102-695X2008000100003
489341 Monocyclanthus vignei: 10.1016/0031-9422(92)80456-O
142860 Euphorbia tirucalli:
1129975 Euphorbia caducifolia: 10.1016/S0031-9422(00)97902-0
3888 Pisum sativum: 10.1016/S0031-9422(00)94844-1
3827 Cicer arietinum: 10.1016/S0031-9422(00)94844-1
3864 Lens culinaris: 10.1016/S0031-9422(00)94844-1
3860 Lathyrus sativus: 10.1016/S0031-9422(00)94844-1
3847 Glycine max: 10.1016/S0031-9422(00)94844-1
3821 Cajanus cajan: 10.1016/S0031-9422(00)94844-1
1091639 Euphorbia oxyphylla: 10.1016/S0031-9422(00)82286-4
3659 Cucumis sativus: 10.1016/0031-9422(82)85222-9
3656 Cucumis melo: 10.1016/0031-9422(82)85222-9
292385 Vitellaria paradoxa: 10.1007/BF02534064
4442 Camellia sinensis: 10.1007/BF02534064
4443 Camellia japonica:
3527 Phytolacca americana: 10.1007/BF02534064
385388 Camellia oleifera:
182300 Camellia sasanqua:
457243 Euphorbia cotinifolia: 10.1016/S0031-9422(00)85859-8
1492770 Euphorbia trigona: 10.1016/0031-9422(88)83136-4
1138358 Euphorbia portulacoides: 10.1016/0031-9422(95)00752-0
212925 Euphorbia lathyris:
239687 Euphorbia kansui:
334664 Euphorbia antiquorum:
1591303 Dacryodes hopkinsii: 10.1590/S0103-50532004000300008
156472 Clusia multiflora: 10.1016/0031-9422(94)00642-7
457265 Euphorbia resinifera: 10.1016/J.PHYTOCHEM.2008.01.004
1281384 Euphorbia sapinii: 10.1016/J.PHYTOL.2011.04.001
316813 Euphorbia abyssinica: 10.1016/S0031-9422(97)01065-0
1333886 Euphorbia aleppica: 10.1016/0031-9422(95)00361-A
1087772 Euphorbia nicaeensis: 10.1055/S-2006-959736
212879 Euphorbia drupifera: 10.1016/J.FITOTE.2007.02.002
457253 Euphorbia jolkinii: 10.1002/HLCA.200890230
1091645 Euphorbia retusa: 10.1016/0031-9422(73)80529-1
1091647 Euphorbia sulcata: 10.1016/0031-9422(73)80529-1
758543 Euphorbia condylocarpa: 10.1007/BF00564277
1091613 Euphorbia boetica: 10.1021/NP50116A020
334689 Euphorbia neriifolia: 10.1080/1057563031000122068
1534498 Euphorbia fusiformis: 10.1055/S-2006-962079
9606 Homo sapiens: -
239687 Euphorbia kansui T. N. Liou ex T. P. Wang: -
33090 Plants: -

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

Hanen Enneb, Khaled Athmouni, Rahma Thabet, Habib Ayadi. Phytochemical Compounds of Euphorbia bivonae Extract and Their Cytotoxicity Effects on the Lethality of Brine Shrimp Artemia salina and Embryonic Kidney (HEK293) Cells. Chemistry & biodiversity. 2023 Apr; ?(?):e202201135. doi: 10.1002/cbdv.202201135. [PMID: 37026603]
Isaac Silvère Gade, Corinne Chadéneau, Richard Tagne Simo, Emmanuel Talla, Alex De Theodore Atchade, Paule Seité, Brigitte Vannier, Sophie Laurent, Céline Henoumont, Armel H Nwabo Kamdje, Jean-Marc Muller. Euphol from Tapinanthus sp. Induces Apoptosis and Affects Signaling Proteins in Glioblastoma and Prostate Cancer Cells. Asian Pacific journal of cancer prevention : APJCP. 2022 12; 23(12):4205-4212. doi: 10.31557/apjcp.2022.23.12.4205. [PMID: 36580003]
Thais Latansio de Oliveira, Ariádine Reder Custodio de Souza, Pâmela Dias Fontana, Milena Carvalho Carneiro, Flávio Luís Beltrame, Iara Jose de Messias Reason, Lorena Bavia. Bioactive Secondary Plant Metabolites from Euphorbia umbellata (PAX) BRUYNS (Euphorbiaceae). Chemistry & biodiversity. 2022 Dec; 19(12):e202200568. doi: 10.1002/cbdv.202200568. [PMID: 36259393]
Weibo Qiao, Wei Feng, Lu Yang, Changfu Li, Xudong Qu, Yansheng Zhang. De Novo Biosynthesis of the Anticancer Compound Euphol in Saccharomyces cerevisiae. ACS synthetic biology. 2021 09; 10(9):2351-2358. doi: 10.1021/acssynbio.1c00257. [PMID: 34445867]
Viviane A O Silva, Marcela N Rosa, Vera Miranda-Gonçalves, Angela M Costa, Aline Tansini, Adriane F Evangelista, Olga Martinho, Adriana C Carloni, Chris Jones, João Paulo Lima, Luiz F Pianowski, Rui Manuel Reis. Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells. Investigational new drugs. 2019 04; 37(2):223-237. doi: 10.1007/s10637-018-0620-y. [PMID: 29931585]
Luiza S Cruz, Thais L de Oliveira, Carla C Kanunfre, Katia S Paludo, Bruno R Minozzo, Ana P Prestes, Mei Wang, Daniel Fernandes, Fábio A Dos Santos, Vamshi K Manda, Shabana I Khan, Zulfiqar Ali, Iara J de Messias-Reason, Bharathi Avula, Ikhlas A Khan, Flávio L Beltrame. Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Aug; 47(?):105-112. doi: 10.1016/j.phymed.2018.04.055. [PMID: 30166094]
Chun-Lin Chen, Ying-Pin Chen, Ming-Wei Lin, Yaw-Bin Huang, Fang-Rong Chang, Tsai-Hui Duh, Deng-Chyang Wu, Wei-Chiang Wu, Yu-Chen Kao, Pei-Hua Yang. Euphol from Euphorbia tirucalli Negatively Modulates TGF-β Responsiveness via TGF-β Receptor Segregation inside Membrane Rafts. PloS one. 2015; 10(10):e0140249. doi: 10.1371/journal.pone.0140249. [PMID: 26448474]
Xu Xie, Yongning Li, Dongna Gao, Yu Zhang, Yanbo Ren. Quantitative determination of euphol in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2014 Sep; 28(9):1229-34. doi: 10.1002/bmc.3151. [PMID: 25237707]
Antonio C M Munhoz, Bruno R Minozzo, Luiza S Cruz, Thaís L Oliveira, Willian M Machado, Airton V Pereira, Daniel Fernandes, Francine A Manente, José C R Vellosa, Angelita Nepel, Andersson Barison, Flávio L Beltrame. Chemical and pharmacological investigation of the stem bark of Synadenium grantii. Planta medica. 2014 Apr; 80(6):458-64. doi: 10.1055/s-0034-1368300. [PMID: 24687740]
Rafael C Dutra, Rafaela F Claudino, Allisson F Bento, Rodrigo Marcon, Eder C Schmidt, Zenilda L Bouzon, Luiz F Pianowski, João B Calixto. Preventive and therapeutic euphol treatment attenuates experimental colitis in mice. PloS one. 2011; 6(11):e27122. doi: 10.1371/journal.pone.0027122. [PMID: 22073270]
Zeng-jun Guo, Jian-feng Zuo, Xiao-qian Bo, Qi-shi Sun. [Study on chemical constituents of Euphorbia hylonoma hand. -Mazz]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Apr; 30(4):412-5. doi: ". [PMID: 17674791]
Han-li Ruan, Yue Zhang, Yong-hui Zhang, Hui-fang Pi, Ji-zhou Wu. [Studies on constituents from roots of Euphorbia hylonoma]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 May; 31(9):742-4. doi: ". [PMID: 17048682]
T Akihisa, J Ogihara, J Kato, K Yasukawa, M Ukiya, S Yamanouchi, K Oishi. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids. 2001 May; 36(5):507-12. doi: 10.1007/s11745-001-0750-4. [PMID: 11432464]
T Akihisa, K Yasukawa, Y Kimura, S Takase, S Yamanouchi, T Tamura. Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects. Chemical & pharmaceutical bulletin. 1997 Dec; 45(12):2016-23. doi: 10.1248/cpb.45.2016. [PMID: 9433772]