5alpha-Cholest-8-en-3beta-ol (BioDeep_00000005327)

 

Secondary id: BioDeep_00000636706, BioDeep_00001892483

human metabolite Endogenous blood metabolite


代谢物信息卡片


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

化学式: C27H46O (386.3548)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 37.99%

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](CCCC(C)C)C)C)C)O
InChI: InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1

描述信息

5a-Cholest-8-en-3b-ol is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decrease and cholesterol precursor sterols such as zymostenol increase. (PMID: 15736111, 16709621, 16477216, 12756385) [HMDB]. 5a-Cholest-8-en-3b-ol is found in many foods, some of which are chinese water chestnut, garden tomato, calabash, and cassava.
5alpha-Cholest-8-en-3beta-ol, also known as zymostenol, is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in the serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decreased and cholesterol precursor sterols such as zymostenol increased (PMID: 15736111, 16709621, 16477216, 12756385).

同义名列表

28 个代谢物同义名

(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol; 3beta-Hydroxy-5alpha-cholest-8(9)-ene; 5α-cholest-8-en-3β-ol; (3beta,5alpha)-Cholest-8-en-3-ol; 5alpha-cholest-8(9)-en-3beta-ol; 5-alpha-Cholest-8-en-3-beta-ol; 3Β-hydroxy-5α-cholest-8(9)-ene; 3beta-Hydroxy-8(9)-cholestene; 3beta-Hydroxycholest-8(9)-ene; 5alpha-cholest-8-en-3beta-ol; Zymostenol, (3beta)-isomer; (3beta,5alpha)Cholestenol; Cholesta-8(9)-en-3beta-ol; (3Β,5α)-cholest-8-en-3-ol; Cholest-8(9)-en-3beta-ol; ​5α-cholest-8-en-3β-ol; ​5a-cholest-8-en-3b-ol; 5a-Cholest-8-en-3b-ol; 5Α-cholest-8-en-3β-ol; delta(8)-Cholestenol; delta8-Cholestenol; Dihydrozymosterol; 8(9)-Cholestenol; SCHEMBL13770750; Δ8-cholestenol; Cholestenol; Zymostenol; 5alpha-Cholest-8-en-3beta-ol



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(2)

PlantCyc(0)

代谢反应

126 个相关的代谢反应过程信息。

Reactome(70)

BioCyc(4)

WikiPathways(4)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(48)

PharmGKB(0)

4 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 ACSS2, GCK, MYH6, NR1H3, NR4A1, PNPLA3, TFCP2L1
Peripheral membrane protein 2 CYP27A1, GCK
Endoplasmic reticulum membrane 2 OST4, PNPLA3
Mitochondrion membrane 1 CYP27A1
Nucleus 6 ACSS2, ASCL1, GCK, NR1H3, NR4A1, TFCP2L1
autophagosome 1 MAP1LC3A
cytosol 7 ACSS2, GCK, GLT1D1, MAP1LC3A, MYH6, NR1H3, NR4A1
trans-Golgi network 1 FAM91A1
nucleoplasm 3 GCK, NR1H3, NR4A1
RNA polymerase II transcription regulator complex 2 ASCL1, NR1H3
Cell membrane 3 ABCG5, ABCG8, TREH
Lipid-anchor 1 MAP1LC3A
Multi-pass membrane protein 2 ABCG5, ABCG8
Golgi apparatus membrane 1 GCK
glutamatergic synapse 1 MAP1LC3A
Golgi membrane 2 GCK, INS
mitochondrial inner membrane 1 CYP27A1
neuronal cell body 1 ASCL1
Cytoplasm, cytosol 2 ACSS2, NR4A1
Presynapse 1 NR4A1
plasma membrane 3 ABCG5, ABCG8, TREH
Membrane 5 ABCG5, ABCG8, PNPLA3, TFCP2L1, TREH
apical plasma membrane 2 ABCG5, ABCG8
basolateral plasma membrane 1 GCK
extracellular exosome 1 TREH
endoplasmic reticulum 1 OST4
extracellular space 3 CCL17, CCL22, INS
mitochondrion 3 CYP27A1, GCK, NR4A1
intracellular membrane-bounded organelle 1 MAP1LC3A
Secreted 3 CCL17, GLT1D1, INS
extracellular region 4 CCL17, CCL22, GLT1D1, INS
mitochondrial matrix 2 ACSS2, CYP27A1
transcription regulator complex 1 NR4A1
nuclear membrane 1 NR4A1
Z disc 1 MYH6
cytoplasmic vesicle 1 FAM91A1
Single-pass type II membrane protein 1 PNPLA3
Apical cell membrane 2 ABCG5, ABCG8
Mitochondrion inner membrane 1 CYP27A1
Cytoplasm, cytoskeleton 1 MAP1LC3A
microtubule 1 MAP1LC3A
myofibril 1 MYH6
Late endosome 1 MAP1LC3A
sarcomere 1 MYH6
receptor complex 3 ABCG5, ABCG8, NR1H3
chromatin 4 ASCL1, NR1H3, NR4A1, TFCP2L1
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
Golgi apparatus, trans-Golgi network 1 FAM91A1
Basolateral cell membrane 1 GCK
Lipid-anchor, GPI-anchor 1 TREH
organelle membrane 1 MAP1LC3A
myosin filament 1 MYH6
myosin II complex 1 MYH6
Endomembrane system 1 MAP1LC3A
endosome lumen 1 INS
Lipid droplet 1 PNPLA3
Cytoplasm, myofibril, sarcomere, M line 1 LRRC39
M band 1 LRRC39
myosin complex 1 MYH6
side of membrane 1 TREH
stress fiber 1 MYH6
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
transport vesicle 1 INS
Single-pass type III membrane protein 1 OST4
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
ATP-binding cassette (ABC) transporter complex 2 ABCG5, ABCG8
Autolysosome 1 MAP1LC3A
oligosaccharyltransferase complex 1 OST4
muscle myosin complex 1 MYH6


文献列表

  • P Simonen, S Li, N K Chua, A-M Lampi, V Piironen, J Lommi, J Sinisalo, A J Brown, E Ikonen, H Gylling. Amiodarone disrupts cholesterol biosynthesis pathway and causes accumulation of circulating desmosterol by inhibiting 24-dehydrocholesterol reductase. Journal of internal medicine. 2020 11; 288(5):560-569. doi: 10.1111/joim.13095. [PMID: 32415867]
  • Helena E Miettinen, Kristiina Rönö, Saila Koivusalo, Beata Stach-Lempinen, Maritta Pöyhönen-Alho, Johan G Eriksson, Timo P Hiltunen, Helena Gylling. Elevated serum squalene and cholesterol synthesis markers in pregnant obese women with gestational diabetes mellitus. Journal of lipid research. 2014 Dec; 55(12):2644-54. doi: 10.1194/jlr.p049510. [PMID: 25301963]
  • Annette Kolb-Mäurer, Karl-Heinz Grzeschik, Dorothea Haas, Eva-Bettina Bröcker, Henning Hamm. Conradi-Hünermann-Happle syndrome (X-linked dominant chondrodysplasia punctata) confirmed by plasma sterol and mutation analysis. Acta dermato-venereologica. 2008; 88(1):47-51. doi: 10.2340/00015555-0337. [PMID: 18176751]
  • H Gylling, S Pyrhönen, E Mäntylä, H Mäenpää, L Kangas, T A Miettinen. Tamoxifen and toremifene lower serum cholesterol by inhibition of delta 8-cholesterol conversion to lathosterol in women with breast cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1995 Dec; 13(12):2900-5. doi: 10.1200/jco.1995.13.12.2900. [PMID: 8523053]
  • H Vanhanen, T A Miettinen. Pravastatin and lovastatin similarly reduce serum cholesterol and its precursor levels in familial hypercholesterolaemia. European journal of clinical pharmacology. 1992; 42(2):127-30. doi: 10.1007/bf00278470. [PMID: 1618241]
  • G J SCHROEPFER. Conversion of zymosterol-C-14 and zymostenol-H3 to cholesterol by rat liver homogenates and intact rats. The Journal of biological chemistry. 1961 Jun; 236(?):1668-73. doi: . [PMID: 13748688]