4,4-Dimethylcholesta-8,14,24-trienol (BioDeep_00000008663)

 

Secondary id: BioDeep_00001871940

human metabolite Endogenous


代谢物信息卡片


(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol

化学式: C29H46O (410.3548)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 13.7%

分子结构信息

SMILES: C12CC[C@@]3([H])C(C)(C)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/C=C(\C)/C)CC=C21
InChI: InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1

描述信息

4,4-Dimethylcholesta-8,14,24-trienol is a product of the enzyme delta14-sterol reductase [EC 1.3.1.70] (KEGG). It is involved in the biosynthesis of steroids and is involved in the conversion of lanosterol to zymosterol. In particular, lanosterol 14-alpha-demethylase, catalyzes the C-14 demethylation of lanosterol to form 4,4-Dimethylcholesta-8,14,24-trienol in the ergosterol biosynthesis pathway. It is thought to be a meiosis activating sterol. [HMDB]
4,4-Dimethylcholesta-8,14,24-trienol is a product of the enzyme delta14-sterol reductase [EC 1.3.1.70] (KEGG). It is involved in the biosynthesis of steroids and is involved in the conversion of lanosterol to zymosterol. In particular, lanosterol 14-alpha-demethylase, catalyzes the C-14 demethylation of lanosterol to form 4,4-Dimethylcholesta-8,14,24-trienol in the ergosterol biosynthesis pathway. It is thought to be a meiosis activating sterol.

同义名列表

20 个代谢物同义名

(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol; (3beta,5alpha)-4,4-Dimethyl-cholesta-8,14,24-trien-3-ol; (3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol; 4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol; 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol; 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-ol; 4,4-Dimethylcholesta-8(9),14,24-trien-3beta-ol; 4,4-Dimethyl cholesta-8,14,24-triene-3-beta-ol; 4,4-Dimethylcholesta-8(9),14,24-trien-3β-ol; 4,4-dimethylcholesta-8,11,24-trien-3beta-ol; 4,4-Dimethylcholesta-8(9),14,24-trien-3b-ol; Follicular fluid meiosis-activating sterol; Follicular fluid meiosis activating sterol; 4,4-Dimethyl-cholesta-8,14,24-trienol; 4,4-dimethylcholesta-8,14,24-trienol; 4,4-Dimechol-8,14,24-trienol; FT-0667405; ST 29:3;O; FF-MAS; 4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(8)

BioCyc(7)

PlantCyc(2)

代谢反应

194 个相关的代谢反应过程信息。

Reactome(120)

BioCyc(14)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

  • cholesterol biosynthesis I: O2 + a reduced [NADPH-hemoprotein reductase] + squalene ⟶ (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O + an oxidized [NADPH-hemoprotein reductase]
  • zymosterol biosynthesis: 14-demethyllanosterol + H+ + O2 + a ferrocytochrome b5 ⟶ 4α-hydroxymethyl-4β-methyl-5α-cholesta-8,24-dien-3β-ol + H2O + a ferricytochrome b5

COVID-19 Disease Map(0)

PathBank(55)

PharmGKB(0)

2 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 ALB, FAS, GDF9, MAPK3, MARK2, MOS, NR1H3
Peripheral membrane protein 2 CYP1B1, HSD17B6
Endoplasmic reticulum membrane 4 AREG, CYP1B1, CYP51A1, FDFT1
Nucleus 4 ALB, AREG, MAPK3, NR1H3
cytosol 5 ALB, FAS, MAPK3, MOS, NR1H3
dendrite 1 MARK2
nuclear body 1 FAS
centrosome 1 ALB
nucleoplasm 3 MAPK3, MARK2, NR1H3
RNA polymerase II transcription regulator complex 1 NR1H3
Cell membrane 2 FAS, RRAS
Lipid-anchor 1 RRAS
Cytoplasmic side 1 RRAS
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 FDFT1
cell surface 2 AREG, FAS
glutamatergic synapse 1 MAPK3
Golgi apparatus 3 ALB, FAS, MAPK3
lysosomal membrane 1 EGF
plasma membrane 6 EGF, EREG, FAS, MAPK3, MARK2, RRAS
Membrane 7 AREG, CYP1B1, CYP51A1, EGF, FAS, FDFT1, MARK2
caveola 1 MAPK3
extracellular exosome 4 ALB, EGF, FAS, RRAS
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 ALB, FDFT1, HSD17B6
extracellular space 7 ALB, AREG, BMP15, EGF, EREG, GDF9, GNRH1
mitochondrion 3 CYP1B1, MAPK3, MARK2
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 3 CYP1B1, CYP51A1, HSD17B6
Microsome membrane 3 CYP1B1, CYP51A1, HSD17B6
Single-pass type I membrane protein 2 EREG, FAS
Secreted 5 ALB, BMP15, GDF9, MDK, SMR3A
extracellular region 9 ALB, AREG, BMP15, EGF, EREG, GDF9, GNRH1, MDK, SMR3A
Single-pass membrane protein 1 CYP51A1
anchoring junction 1 ALB
external side of plasma membrane 1 FAS
Early endosome 1 MAPK3
Membrane raft 1 FAS
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 MAPK3, RRAS
lateral plasma membrane 1 MARK2
Late endosome 1 MAPK3
receptor complex 1 NR1H3
ciliary basal body 1 ALB
chromatin 1 NR1H3
cytoskeleton 1 MAPK3
centriole 1 ALB
spindle pole 1 ALB
actin filament 1 MARK2
blood microparticle 1 ALB
nuclear envelope 1 MAPK3
Membrane, caveola 1 MAPK3
Cell projection, dendrite 1 MARK2
Melanosome 1 FAS
pseudopodium 1 MAPK3
endoplasmic reticulum lumen 3 ALB, BMP15, MAPK3
platelet alpha granule lumen 2 ALB, EGF
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 AREG
ER to Golgi transport vesicle membrane 1 AREG
[Epiregulin]: Secreted, extracellular space 1 EREG
[Proepiregulin]: Cell membrane 1 EREG
clathrin-coated endocytic vesicle membrane 3 AREG, EGF, EREG
CD95 death-inducing signaling complex 1 FAS
death-inducing signaling complex 1 FAS
[Isoform 1]: Cell membrane 1 FAS
glycogen granule 1 FAS
ciliary transition fiber 1 ALB
microtubule bundle 1 MARK2


文献列表

  • Leonardo Gatticchi, Bruno Cerra, Paolo Scarpelli, Lara Macchioni, Bartolomeo Sebastiani, Antimo Gioiello, Rita Roberti. Selected cholesterol biosynthesis inhibitors produce accumulation of the intermediate FF-MAS that targets nucleus and activates LXRα in HepG2 cells. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 Sep; 1862(9):842-852. doi: 10.1016/j.bbalip.2017.05.004. [PMID: 28499814]
  • Fengchao Wang, Jie Yang, Haibin Wang, Guoliang Xia. Gonadotropin-regulated expressions of lanosterol 14alpha-demethylase, sterol Delta14-reductase and C-4 sterol methyl oxidase contribute to the accumulation of meiosis-activating sterol in rabbit gonads. Prostaglandins & other lipid mediators. 2010 Jun; 92(1-4):25-32. doi: 10.1016/j.prostaglandins.2010.02.002. [PMID: 20193772]
  • Christian Grøndahl, Jens Breinholt, Philip Wahl, Anthony Murray, Thomas Høst Hansen, Inger Faerge, Carsten E Stidsen, Kirsten Raun, Christa Hegele-Hartung. Physiology of meiosis-activating sterol: endogenous formation and mode of action. Human reproduction (Oxford, England). 2003 Jan; 18(1):122-9. doi: 10.1093/humrep/deg028. [PMID: 12525452]
  • I Faerge, C Grøndahl, J L Ottesen, P Hyttel. Autoradiographic localization of specific binding of meiosis-activating sterol to cumulus-oocyte complexes from marmoset, cow, and mouse. Biology of reproduction. 2001 Feb; 64(2):527-36. doi: 10.1095/biolreprod64.2.527. [PMID: 11159355]
  • C Grøndahl, T H Hansen, K Marky-Nielsen, J L Ottesen, P Hyttel. Human oocyte maturation in vitro is stimulated by meiosis-activating sterol. Human reproduction (Oxford, England). 2000 Dec; 15 Suppl 5(?):3-10. doi: 10.1093/humrep/15.suppl_5.3. [PMID: 11263536]
  • Y Yoshida, C Yamashita, M Noshiro, M Fukuda, Y Aoyama. Sterol 14-demethylase P450 activity expressed in rat gonads: contribution to the formation of mammalian meiosis-activating sterol. Biochemical and biophysical research communications. 1996 Jun; 223(3):534-8. doi: 10.1006/bbrc.1996.0929. [PMID: 8687430]