ST 27:2;O3 (BioDeep_00000011218)

 

Secondary id: BioDeep_00000010803, BioDeep_00000011645, BioDeep_00000011649, BioDeep_00000011651, BioDeep_00000019610, BioDeep_00001869404, BioDeep_00001870401


代谢物信息卡片


3beta,5beta-Ketodiol; 2,22,25-Trideoxyecdysone; 3beta,14alpha-Dihydroxy-5beta-cholest-7-en-6-one

化学式: C27H44O3 (416.329)
中文名称: 7,12-二羟基-4-胆甾烯-3-酮
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 22.33%

分子结构信息

SMILES: C12=CC([C@]3([H])C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2(O)CC[C@@]1([C@H](C)CCCC(C)C)[H])=O
InChI: InChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)20-11-14-27(30)22-16-24(29)23-15-19(28)9-12-25(23,4)21(22)10-13-26(20,27)5/h16-21,23,28,30H,6-15H2,1-5H3/t18-,19+,20-,21+,23+,25-,26-,27-/m1/s1

描述信息

同义名列表

61 个代谢物同义名

3beta,14alpha-Dihydroxy-5beta-cholest-7-en-6-one; 3beta,14-dihydroxy-5beta-cholest-7-en-6-one; 2,22,25-trideoxyecdysone; ST 27:2;O3; (5alpha,25S)-3-oxocholestan-26-oic acid; (25S)-dafachronic acid; (25S)-3beta-hydroxycholest-5-en-26-oic acid; (25S)-cholestenoic acid; 7alpha,24S-dihydroxycholest-4-en-3-one; 7alpha,24S-dihydroxy-4-cholesten-3-one; 4-cholesten-7alpha,24S-diol-3-one; (25R)-7-oxo-cholest-5-en-3beta,27-diol; 3beta,27-dihydroxy-5-cholesten-7-one; 3beta,26-dihydroxy-5-cholesten-7-one; 7alpha,24-dihydroxycholest-4-en-3-one; 4-cholesten-7alpha,24-diol-3-one; 7alpha,26-dihydroxycholest-4-en-3-one; 4-cholesten-7alpha,26-diol-3-one; 3alpha-Hydroxy-5beta-cholest-24-en-26-oic acid; 7alpha,12alpha-Dihydroxycholest-4-en-3-one; 7α,12α-dihydroxycholest-4-en-3-one; 7alpha,25-Dihydroxycholest-4-en-3-one; 7alpha,25-dihydroxycholestenone; 3beta-Hydroxycholest-5-en-25R-26-oic acid; 3beta-hydroxy-5-cholestenoic acid; hydroxycholestenoic acid; Cholestenoic acid; 20S-24S-epoxy-cholest-5-en-3beta,22S-diol; Verrucorosteroid F; 5alpha-cholesta-24-en-3beta,20beta-diol-23-one; (25S)-7alpha,26-Dihydroxycholest-4-en-3-one; 7alpha,(25S)26-Dihydroxycholest-4-en-3-one; (25R)-7alpha,26-dihydroxycholest-4-en-3-one; 7alpha,(25R)26-Dihydroxycholest-4-en-3-one; 3beta,25-Dihydroxycholest-5-en-7-one; 25-hydroxy 7-keto cholesterol; 25-Hydroxy-7-oxocholesterol; 3beta,4beta-dihydroxycholest-8(9)-en-23-one; 3beta,4beta-dihydroxycholest-7(8)-en-23-one; 3beta,4beta-dihydroxycholest-5(6)-en-23-one; 3beta,4beta-dihydroxycholesta-5-ene-23-one; 5alpha,6alpha-24S,25-diepoxy-cholestan-3beta-ol; 5alpha,6alpha-24S,25-diepoxy-cholesterol; 5alpha,6alpha-24S,25-Diepoxycholesterol; (24S,25)-Epoxycholesterol alpha-epoxide; 5,6-24(S),25-Diepoxycholesterol; 24,25-5,6 diepoxycholesterol; 7alpha-hydroperoxy-cholesta-5,8-dien-3beta-ol; 7-OOH-5,8-dien-3beta-ol; 3beta,6alpha-dihydroxy-5alpha-cholesta-9(11)-en-23-one; Dihydromarthasterone; 20S-Hydroxy-5-alpha-cholestane-3,16-dione; 20S-Hydroxycholestane-3,16-dione; 5,6alpha-epoxy-cholest-8(14)-en-3beta,7beta-diol; 5,6alpha-epoxy-cholest-8(14)-en-3beta,7alpha-diol; 5,6alpha-epoxy-cholest-7-en-3beta,9alpha-diol; 3beta,5beta-Ketodiol; 2,22,25-Trideoxyecdysone; 3beta,14alpha-Dihydroxy-5beta-cholest-7-en-6-one; 7alpha,26-Dihydroxy-4-cholesten-3-one; 2,22,25-Trideoxyecdysone; 5,6-24(S),25-Diepoxycholesterol; 4-Cholesten-7alpha,12alpha-diol-3-one



数据库引用编号

90 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(12)

BioCyc(0)

PlantCyc(0)

代谢反应

165 个相关的代谢反应过程信息。

Reactome(162)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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 10 AKR1D1, ALB, APOE, DNMT3A, ESR1, MVK, NR1H2, NR1H3, PCSK9, PRKAA2
Peripheral membrane protein 3 CYP1B1, CYP27A1, ESR1
Endoplasmic reticulum membrane 3 CYP1B1, CYP7B1, CYP8B1
Mitochondrion membrane 1 CYP27A1
Nucleus 10 ALB, APOE, DNMT1, DNMT3A, DNMT3B, ESR1, NR1H2, NR1H3, NR1H4, PRKAA2
cytosol 8 AKR1D1, ALB, APOA1, ESR1, MVK, NR1H2, NR1H3, PRKAA2
dendrite 2 APOE, PRKAA2
centrosome 1 ALB
nucleoplasm 8 DNMT1, DNMT3A, DNMT3B, ESR1, NR1H2, NR1H3, NR1H4, PRKAA2
RNA polymerase II transcription regulator complex 3 NR1H2, NR1H3, NR1H4
Cell membrane 1 ESR1
Cytoplasmic side 1 ESR1
Multi-pass membrane protein 1 CYP7B1
cell surface 1 PCSK9
glutamatergic synapse 1 APOE
Golgi apparatus 5 ALB, APOE, ESR1, PCSK9, PRKAA2
Golgi membrane 1 INS
lysosomal membrane 1 PCSK9
mitochondrial inner membrane 1 CYP27A1
neuronal cell body 2 APOE, PRKAA2
Lysosome 1 PCSK9
endosome 1 PCSK9
plasma membrane 4 APOA1, APOE, ESR1, PCSK9
Membrane 5 APOE, CYP1B1, CYP7B1, ESR1, PRKAA2
axon 1 PRKAA2
extracellular exosome 3 ALB, APOA1, APOE
endoplasmic reticulum 3 ALB, APOE, PCSK9
extracellular space 5 ALB, APOA1, APOE, INS, PCSK9
perinuclear region of cytoplasm 1 PCSK9
mitochondrion 3 CYP1B1, CYP27A1, DNMT1
protein-containing complex 2 ALB, ESR1
intracellular membrane-bounded organelle 2 CYP1B1, MVK
Microsome membrane 3 CYP1B1, CYP7B1, CYP8B1
pericentric heterochromatin 1 DNMT1
Secreted 5 ALB, APOA1, APOE, INS, PCSK9
extracellular region 5 ALB, APOA1, APOE, INS, PCSK9
Single-pass membrane protein 1 CYP8B1
mitochondrial matrix 1 CYP27A1
anchoring junction 1 ALB
transcription regulator complex 1 ESR1
Endosome, multivesicular body 1 APOE
Extracellular vesicle 2 APOA1, APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 2 APOA1, APOE
high-density lipoprotein particle 2 APOA1, APOE
low-density lipoprotein particle 2 APOA1, APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 2 APOA1, APOE
cytoplasmic vesicle 1 APOA1
Early endosome 3 APOA1, APOE, PCSK9
COPII-coated ER to Golgi transport vesicle 1 PCSK9
Mitochondrion inner membrane 1 CYP27A1
heterochromatin 1 DNMT3A
extracellular matrix 1 APOE
Peroxisome 1 MVK
collagen-containing extracellular matrix 2 APOA1, APOE
nuclear speck 1 PRKAA2
Late endosome 1 PCSK9
receptor complex 2 NR1H3, NR1H4
ciliary basal body 1 ALB
chromatin 4 ESR1, NR1H2, NR1H3, NR1H4
Chromosome 1 DNMT3A
[Isoform 3]: Nucleus 1 NR1H4
centriole 1 ALB
Secreted, extracellular space 1 APOE
spindle pole 1 ALB
blood microparticle 3 ALB, APOA1, APOE
endosome lumen 1 INS
female germ cell nucleus 1 DNMT1
Melanosome 1 APOE
cytoplasmic stress granule 1 PRKAA2
euchromatin 3 DNMT3A, ESR1, NR1H4
replication fork 1 DNMT1
secretory granule lumen 2 APOA1, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 5 ALB, APOA1, APOE, INS, PCSK9
nuclear matrix 1 DNMT3A
platelet alpha granule lumen 1 ALB
XY body 1 DNMT3A
endocytic vesicle 1 APOA1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
chromosome, centromeric region 1 DNMT3A
clathrin-coated endocytic vesicle membrane 1 APOE
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 2 ESR1, NR1H4
synaptic cleft 1 APOE
endolysosome membrane 1 PCSK9
nucleotide-activated protein kinase complex 1 PRKAA2
extrinsic component of external side of plasma membrane 1 PCSK9
[Isoform 4]: Nucleus 1 NR1H4
discoidal high-density lipoprotein particle 1 APOE
spherical high-density lipoprotein particle 1 APOA1
endocytic vesicle lumen 2 APOA1, APOE
PCSK9-LDLR complex 1 PCSK9
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
catalytic complex 2 DNMT3A, DNMT3B
PCSK9-AnxA2 complex 1 PCSK9
ciliary transition fiber 1 ALB


文献列表

  • Yaping Wang, William M Pandak, Phillip B Hylemon, Hae-Ki Min, John Min, Michael Fuchs, Arun J Sanyal, Shunlin Ren. Cholestenoic Acid as Endogenous Epigenetic Regulator Decreases Hepatocyte Lipid Accumulation in Vitro and in Vivo. American journal of physiology. Gastrointestinal and liver physiology. 2023 Nov; ?(?):. doi: 10.1152/ajpgi.00184.2023. [PMID: 37961761]
  • Lautaro D Alvarez, María V Dansey, María F Ogara, Carina I Peña, René Houtman, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Cholestenoic acid analogues as inverse agonists of the liver X receptors. The Journal of steroid biochemistry and molecular biology. 2020 05; 199(?):105585. doi: 10.1016/j.jsbmb.2020.105585. [PMID: 31931135]
  • Peter J Crick, Eylan Yutuc, Jonas Abdel-Khalik, Ahmed Saeed, Christer Betsholtz, Guillem Genove, Ingemar Björkhem, Yuqin Wang, William J Griffiths. Formation and metabolism of oxysterols and cholestenoic acids found in the mouse circulation: Lessons learnt from deuterium-enrichment experiments and the CYP46A1 transgenic mouse. The Journal of steroid biochemistry and molecular biology. 2019 12; 195(?):105475. doi: 10.1016/j.jsbmb.2019.105475. [PMID: 31541728]
  • William J Griffiths, Peter J Crick, Anna Meljon, Spyridon Theofilopoulos, Jonas Abdel-Khalik, Eylan Yutuc, Josie E Parker, Diane E Kelly, Steven L Kelly, Ernest Arenas, Yuqin Wang. Additional pathways of sterol metabolism: Evidence from analysis of Cyp27a1-/- mouse brain and plasma. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2019 02; 1864(2):191-211. doi: 10.1016/j.bbalip.2018.11.006. [PMID: 30471425]
  • Cristian R Rodriguez, Lautaro D Alvarez, M Virginia Dansey, Luciano S Paolo, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Fluorinated oxysterol analogues: Synthesis, molecular modelling and LXRβ activity. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):268-276. doi: 10.1016/j.jsbmb.2016.07.001. [PMID: 27452335]
  • Lautaro D Álvarez, M Virginia Dansey, Diego Y Grinman, Daniela Navalesi, Gisela A Samaja, M Celeste Del Fueyo, Niek Bastiaensen, René Houtman, Darío A Estrin, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Destabilization of the torsioned conformation of a ligand side chain inverts the LXRβ activity. Biochimica et biophysica acta. 2015 Dec; 1851(12):1577-86. doi: 10.1016/j.bbalip.2015.09.007. [PMID: 26434697]
  • Peter J Crick, Lien Beckers, Myriam Baes, Paul P Van Veldhoven, Yuqin Wang, William J Griffiths. The oxysterol and cholestenoic acid profile of mouse cerebrospinal fluid. Steroids. 2015 Jul; 99(Pt B):172-7. doi: 10.1016/j.steroids.2015.02.021. [PMID: 25759118]
  • Spyridon Theofilopoulos, William J Griffiths, Peter J Crick, Shanzheng Yang, Anna Meljon, Michael Ogundare, Satish Srinivas Kitambi, Andrew Lockhart, Karin Tuschl, Peter T Clayton, Andrew A Morris, Adelaida Martinez, M Ashwin Reddy, Andrea Martinuzzi, Maria T Bassi, Akira Honda, Tatsuki Mizuochi, Akihiko Kimura, Hiroshi Nittono, Giuseppe De Michele, Rosa Carbone, Chiara Criscuolo, Joyce L Yau, Jonathan R Seckl, Rebecca Schüle, Ludger Schöls, Andreas W Sailer, Jens Kuhle, Matthew J Fraidakis, Jan-Åke Gustafsson, Knut R Steffensen, Ingemar Björkhem, Patrik Ernfors, Jan Sjövall, Ernest Arenas, Yuqin Wang. Cholestenoic acids regulate motor neuron survival via liver X receptors. The Journal of clinical investigation. 2014 Nov; 124(11):4829-42. doi: 10.1172/jci68506. [PMID: 25271621]
  • Shoujiro Ogawa, Biao Zhou, Yusuke Kimoto, Kaoru Omura, Akiko Kobayashi, Tatsuya Higashi, Kuniko Mitamura, Shigeo Ikegawa, Lee R Hagey, Alan F Hofmann, Takashi Iida. An efficient synthesis of 7α,12α-dihydroxy-4-cholesten-3-one and its biological precursor 7α-hydroxy-4-cholesten-3-one: Key intermediates in bile acid biosynthesis. Steroids. 2013 Sep; 78(9):927-37. doi: 10.1016/j.steroids.2013.05.011. [PMID: 23707572]
  • William J Griffiths, Peter J Crick, Yuchen Wang, Michael Ogundare, Karin Tuschl, Andrew A Morris, Brian W Bigger, Peter T Clayton, Yuqin Wang. Analytical strategies for characterization of oxysterol lipidomes: liver X receptor ligands in plasma. Free radical biology & medicine. 2013 Jun; 59(?):69-84. doi: 10.1016/j.freeradbiomed.2012.07.027. [PMID: 22846477]
  • Cun S Fang, Ying C Wang, Tao H Zhang, Jing Wu, Wei Wang, Chun Wang, Ming Y Zhang. Clinical significance of serum lipids in idiopathic pulmonary alveolar proteinosis. Lipids in health and disease. 2012 Jan; 11(?):12. doi: 10.1186/1476-511x-11-12. [PMID: 22252101]
  • Xinlun Tian, Jinmei Luo, Kai-Feng Xu, Lan Wang, Jiong Zhou, Ruie Feng, Yaosong Gui, Juan Wang, Wenbing Xu, Yi Xiao, Yuanjue Zhu. Impaired lipid metabolism in idiopathic pulmonary alveolar proteinosis. Lipids in health and disease. 2011 Apr; 10(?):54. doi: 10.1186/1476-511x-10-54. [PMID: 21486485]
  • David N Douda, Nicole Farmakovski, Sharon Dell, Hartmut Grasemann, Nades Palaniyar. SP-D counteracts GM-CSF-mediated increase of granuloma formation by alveolar macrophages in lysinuric protein intolerance. Orphanet journal of rare diseases. 2009 Dec; 4(?):29. doi: 10.1186/1750-1172-4-29. [PMID: 20030831]
  • A Babiker, S Dzeletovic, B Wiklund, N Pettersson, J Salonen, K Nyyssönen, M Eriksson, U Diczfalusy, I Björkhem. Patients with atherosclerosis may have increased circulating levels of 27-hydroxycholesterol and cholestenoic acid. Scandinavian journal of clinical and laboratory investigation. 2005; 65(5):365-75. doi: 10.1080/00365510510025746. [PMID: 16081359]
  • Steve Meaney, Tracey L Bonfield, Magnus Hansson, Amir Babiker, Mani S Kavuru, Mary Jane Thomassen. Serum cholestenoic acid as a potential marker of pulmonary cholesterol homeostasis: increased levels in patients with pulmonary alveolar proteinosis. Journal of lipid research. 2004 Dec; 45(12):2354-60. doi: 10.1194/jlr.m400302-jlr200. [PMID: 15466366]
  • Yoshikazu Ota, Tada-Aki Eto, Shun-Ichi Tanaka, Hideto Sueta, Hironori Shiotsuki, Yorio Maeda, Mizuho Une, Kazuo Chijiiwa. Assay method for mitochondrial sterol 27-hydroxylase with 7alpha-hydroxy-4-cholesten-3-one as a substrate in the rat liver. Journal of lipid research. 2003 Dec; 44(12):2400-5. doi: 10.1194/jlr.d200045-jlr200. [PMID: 12951370]
  • Magnus Hansson, Ewa Ellis, Mary C Hunt, Gerd Schmitz, Amir Babiker. Marked induction of sterol 27-hydroxylase activity and mRNA levels during differentiation of human cultured monocytes into macrophages. Biochimica et biophysica acta. 2003 Feb; 1593(2-3):283-9. doi: 10.1016/s0167-4889(02)00398-1. [PMID: 12581873]
  • X Fu, J G Menke, Y Chen, G Zhou, K L MacNaul, S D Wright, C P Sparrow, E G Lund. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. The Journal of biological chemistry. 2001 Oct; 276(42):38378-87. doi: 10.1074/jbc.m105805200. [PMID: 11504730]
  • A Honda, G Salen, Y Matsuzaki, A K Batta, G Xu, E Leitersdorf, G S Tint, S K Erickson, N Tanaka, S Shefer. Differences in hepatic levels of intermediates in bile acid biosynthesis between Cyp27(-/-) mice and CTX. Journal of lipid research. 2001 Feb; 42(2):291-300. doi: . [PMID: 11181760]
  • I Björkhem, H Oftebro, S Skrede, J I Pedersen. Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. Journal of lipid research. 1981 Feb; 22(2):191-200. doi: . [PMID: 7017048]
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