fecosterol (BioDeep_00000005553)

human metabolite

代谢物信息卡片

(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

化学式: C28H46O (398.3548466)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.9%

分子结构信息

SMILES: C1[C@@H](C[C@H]2[C@](C1)(C1=C(CC2)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=C)C(C)C)C)C)C)O
InChI: InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18,20-22,24-25,29H,3,7-17H2,1-2,4-6H3/t20-,21+,22+,24-,25+,27+,28-/m1/s1

描述信息

Fecosterol, also known as 24-methylene-5alpha-cholest-8-en-3beta-ol or delta-8(24),28-ergostadienol, belongs to ergosterols and derivatives class of compounds. Those are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, fecosterol is considered to be a sterol lipid molecule. Fecosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Fecosterol can be synthesized from 5alpha-ergostane. Fecosterol can also be synthesized into fecosterol ester. Fecosterol can be found in a number of food items such as jews ear, lima bean, persimmon, and european plum, which makes fecosterol a potential biomarker for the consumption of these food products. Fecosterol may be a unique S.cerevisiae (yeast) metabolite. Fecosterol is a sterol made by certain fungi and lichens .

同义名列表

15 个代谢物同义名

(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol; 8(9), (5-|A)-CHOLESTEN-24-METHYLENE-3-|A-OL; 24-methylene-5alpha-cholest-8-en-3beta-ol; 24-Methylcholesta-8,24(28)-dien-3beta-ol; 24-methylene-cholest-8-en-3β-ol; 24-Methylene-5a-cholest-8-en-3b-ol; 24-Methylene-5α-cholest-8-en-3β-ol; 24-methylene-cholest-8-en-3beta-ol; 24-Methylene-cholest-8-en-3β-ol; 24-Methylene-cholest-8-en-3b-ol; Ergosta-8,24(28)-dien-3beta-ol; (3beta)-Isomer OF fecosterol; delta-8(24),28-Ergostadienol; Δ-8(24),28-ergostadienol; Fecosterol

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:17038
KEGG: C04525
PubChem: 3375145
PubChem: 440371
HMDB: HMDB0304351
Metlin: METLIN41726
MetaCyc: FECOSTEROL
KNApSAcK: C00023751
foodb: FDB030856
chemspider: 389329
CAS: 516-86-9
PMhub: MS000018379
PubChem: 7136
LipidMAPS: LMST01030095
3DMET: B01753
NIKKAJI: J16.117I
RefMet: Fecosterol

分类词条

代谢反应

17 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(9)

superpathway of ergosterol biosynthesis I: (3S)-2,3-epoxy-2,3-dihydrosqualene ⟶ lanosterol
ergosterol biosynthesis I: SAM + zymosterol ⟶ H⁺ + SAH + fecosterol
superpathway of ergosterol biosynthesis: NADP⁺ + ergosterol ⟶ H⁺ + NADPH + ergosta-5,7,22,24(28)-tetraen-3-β-ol
ergosterol biosynthesis: NADP⁺ + ergosterol ⟶ H⁺ + NADPH + ergosta-5,7,22,24(28)-tetraen-3-β-ol
superpathway of sterol biosynthesis: 4-methyl-2-oxopentanoate + NAD⁺ + coenzyme A ⟶ CO₂ + NADH + isovaleryl-CoA
ergosterol biosynthesis: H⁺ + NADPH + O₂ + lanosterol ⟶ 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + H₂O + NADP⁺ + formate
ergosterol biosynthesis: NADP⁺ + ergosterol ⟶ 5,7,22,24(28)-ergostatetraenol + H⁺ + NADPH
ergosterol biosynthesis: 5,7,22,24(28)-ergostatetraenol + NADPH ⟶ NADP⁺ + ergosterol
superpathway of ergosterol biosynthesis: H⁺ + NADPH + O₂ + lanosterol ⟶ 4,4-dimethyl-5-α-cholesta-8,14,24-trien-3-β-ol + NADP⁺ + formate

WikiPathways(1)

Ergosterol biosynthesis: PreSqualene-PP ⟶ Squalene

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(7)

Steroid Biosynthesis: Farnesyl pyrophosphate + NADPH ⟶ NADP + Pyrophosphate + Squalene
Cholesterol biosynthesis and metabolism CE(14:0): Desmosterol ⟶ Cholesterol
Cholesterol biosynthesis and metabolism CE(10:0): Desmosterol ⟶ Cholesterol
Cholesterol Biosynthesis and Metabolism CE(12:0): Cholesterol + Lauroyl-CoA ⟶ CE(12:0) + Coenzyme A
Cholesterol Biosynthesis and Metabolism CE(16:0): Cholesterol + Palmityl-CoA ⟶ CE(16:0) + Coenzyme A
Cholesterol biosynthesis and metabolism CE(18:0): Desmosterol ⟶ Cholesterol
Cholesterol Biosynthesis and Metabolism: Cholesterol + long-chain fatty acyl-CoA ⟶ Cholesteryl ester + Coenzyme A

PharmGKB(0)

11 个相关的物种来源信息

5476 - Candida albicans: 10.1016/J.ABB.2010.10.008
4903 - Cyberlindnera jadinii: 10.1016/J.ABB.2010.10.008
97096 - Eutypa lata: 10.1016/0031-9422(96)00227-0
9606 - Homo sapiens: -
5022 - Leptosphaeria maculans: 10.1016/S0031-9422(02)00505-8
5141 - Neurospora crassa: 10.1007/BF00486063
2075271 - Phaeosphaeria sowerbyi: 10.1016/S0031-9422(02)00505-8
4837 - Phycomyces blakesleeanus: 10.1021/NP980199H
714648 - Rubus cochinchinensis: 10.1016/S0031-9422(00)81419-3
211815 - Rubus plicatus: 10.1016/S0031-9422(00)81419-3
4577 - Zea mays: 10.1016/S0031-9422(00)81419-3

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

Yanli Qi, Hui Liu, Jiayin Yu, Xiulai Chen, Liming Liu. Med15B Regulates Acid Stress Response and Tolerance in Candida glabrata by Altering Membrane Lipid Composition. Applied and environmental microbiology. 2017 09; 83(18):. doi: 10.1128/aem.01128-17. [PMID: 28710262]
Anna Andolfi, Laura Mugnai, Jordi Luque, Giuseppe Surico, Alessio Cimmino, Antonio Evidente. Phytotoxins produced by fungi associated with grapevine trunk diseases. Toxins. 2011 12; 3(12):1569-605. doi: 10.3390/toxins3121569. [PMID: 22295177]
Ashutosh Singh, Rajendra Prasad. Comparative lipidomics of azole sensitive and resistant clinical isolates of Candida albicans reveals unexpected diversity in molecular lipid imprints. PloS one. 2011 Apr; 6(4):e19266. doi: 10.1371/journal.pone.0019266. [PMID: 21559392]
Fernando Alvarez-Vasquez, Howard Riezman, Yusuf A Hannun, Eberhard O Voit. Mathematical modeling and validation of the ergosterol pathway in Saccharomyces cerevisiae. PloS one. 2011; 6(12):e28344. doi: 10.1371/journal.pone.0028344. [PMID: 22194828]
Agata Leszczynska, Beata Burzynska, Danuta Plochocka, Joanna Kaminska, Magdalena Zimnicka, Magdalena Kania, Marek Kiliszek, Monika Wysocka-Kapcinska, Witold Danikiewicz, Anna Szkopinska. Investigating the effects of statins on cellular lipid metabolism using a yeast expression system. PloS one. 2009 Dec; 4(12):e8499. doi: 10.1371/journal.pone.0008499. [PMID: 20041128]
Wanderley de Souza, Juliany Cola Fernandes Rodrigues. Sterol Biosynthesis Pathway as Target for Anti-trypanosomatid Drugs. Interdisciplinary perspectives on infectious diseases. 2009; 2009(?):642502. doi: 10.1155/2009/642502. [PMID: 19680554]
Paolo Maria Guarrera, Fernando Lucchese, Simone Medori. Ethnophytotherapeutical research in the high Molise region (Central-Southern Italy). Journal of ethnobiology and ethnomedicine. 2008 Mar; 4(?):7. doi: 10.1186/1746-4269-4-7. [PMID: 18334029]