Cholestenone (BioDeep_00000001251)

Secondary id: BioDeep_00000405402, BioDeep_00000413212, BioDeep_00001868267

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite

代谢物信息卡片

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

化学式: C27H44O (384.3391974)
中文名称: 胆甾烯酮
谱图信息: 最多检出来源 Homo sapiens(feces) 0.03%

Reviewed

Last reviewed on 2024-09-26.

Cite this Page

Cholestenone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cholestenone (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000001251). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
InChI: InChI=1S/C27H44O/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/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

描述信息

Cholestenone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholestenone is considered to be a sterol lipid molecule. Cholestenone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Cholestenone is a dehydrocholestanone. It is a product of cholesterol oxidase {EC 1.1.3.6] in the Bile acid biosynthesis pathway (KEGG). [HMDB]
Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2].
Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2].

同义名列表

20 个代谢物同义名

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (17beta)-17-Octylandrost-4-en-3-one; (17b)-17-Octylandrost-4-en-3-one; (17Β)-17-octylandrost-4-en-3-one; (+)-3-Oxo-4-cholestene; delta4-Cholesten-3-one; (+)-4-Cholesten-3-one; 3-Keto-4-cholestene; delta4-Cholestenone; 3-Oxocholest-4-ene; Cholest-4-en-3-one; Δ4-cholesten-3-one; D4-Cholesten-3-one; 3-Oxo-4-cholestene; 4-Cholesten-3-one; Δ4-cholestenone; D4-Cholestenone; 4-Cholestenone; Cholesterone; Cholestenone

数据库引用编号

21 个数据库交叉引用编号

ChEBI: CHEBI:16175
KEGG: C00599
KEGGdrug: D94645
PubChem: 91477
PubChem: 440
HMDB: HMDB0000921
Metlin: METLIN3898
ChEMBL: CHEMBL63243
MetaCyc: CPD-323
KNApSAcK: C00036093
foodb: FDB022319
chemspider: 82602
CAS: 601-57-0
PMhub: MS000000207
PubChem: 3875
LipidMAPS: LMST01010015
PDB-CCD: K2B
3DMET: B01291
NIKKAJI: J73F
RefMet: Cholestenone
medchemexpress: HY-113365

分类词条

代谢反应

15 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(14)

superpathway of cholesterol degradation II (cholesterol dehydrogenase): 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
cholesterol degradation to androstenedione II (cholesterol dehydrogenase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
superpathway of cholesterol degradation II (cholesterol dehydrogenase): 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + O₂ ⟶ (1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1 (10),2-dien-4-oate + H⁺
cholesterol degradation to androstenedione II (cholesterol dehydrogenase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
superpathway of cholesterol degradation I (cholesterol oxidase): 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMNH₂ + O₂ ⟶ 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + FMN + H⁺ + H₂O
cholesterol degradation to androstenedione I (cholesterol oxidase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
cholesterol degradation to androstenedione I (cholesterol oxidase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
superpathway of cholesterol degradation II (cholesterol dehydrogenase): NAD⁺ + coenzyme A + propanal ⟶ H⁺ + NADH + propanoyl-CoA
cholesterol degradation to androstenedione I (cholesterol oxidase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
cholesterol degradation to androstenedione II (cholesterol dehydrogenase): 17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA ⟶ androst-4-ene-3,17-dione + propanoyl-CoA
cholesterol degradation to androstenedione II (cholesterol dehydrogenase): NAD⁺ + cholesterol ⟶ H⁺ + NADH + cholest-5-en-3-one
superpathway of cholesterol degradation I (cholesterol oxidase): O₂ + cholesterol ⟶ cholest-5-en-3-one + hydrogen peroxide
cholesterol degradation to androstenedione I (cholesterol oxidase): O₂ + cholesterol ⟶ cholest-5-en-3-one + hydrogen peroxide
superpathway of cholesterol degradation II (cholesterol dehydrogenase): NAD⁺ + cholesterol ⟶ H⁺ + NADH + cholest-5-en-3-one

WikiPathways(1)

Biosynthesis and regulation of nematode bile acids: 7-Dehydrocholesterol ⟶ Lathosterol

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

19 个相关的物种来源信息

385024 - Acanthophora spicifera: 10.1016/S0031-9422(98)00171-X
942674 - Amphilectus fucorum: 10.1016/S0040-4020(01)85914-7
237119 - Axinella verrucosa: 10.1039/C39780000524
1489463 - Bombax anceps: 10.4067/S0717-97072010000300010
10212 - Bugula neritina: 10.1007/S10600-010-9625-2
76781 - Cinachyrella: 10.1016/S0040-4039(97)00163-9
1479643 - Dendrophyllia cornigera: 10.1016/J.STEROIDS.2005.09.004
1142948 - Dracaena cinnabari: 10.1016/0031-9422(94)00743-D
6047 - Geodia cydonium: 10.1021/NP50071A019
9606 - Homo sapiens: -
3879 - Medicago sativa: 10.3389/FPLS.2017.01208
710152 - Neogymnocrinus richeri: 10.1016/0305-0491(91)90234-5
173456 - Peyssonnelia: 10.1016/J.BMC.2010.10.010
569429 - Phallusia nigra: 10.1016/0039-128X(82)90021-6
2972 - Pyrocystis lunula: 10.1016/0039-128X(82)90042-3
129788 - Ruditapes philippinarum: 10.2331/SUISAN.44.525
38868 - Salvia officinalis: 10.1080/10575639208048902
1132405 - Salvia tomentosa: 10.1080/10575639208048902
1883 - Streptomyces: 10.1080/14786410600899142

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

Josiane Elia, Delphine Carbonnelle, Cédric Logé, Lucie Ory, Jean-Michel Huvelin, Mona Tannoury, Mona Diab-Assaf, Karina Petit, Hassan Nazih. 4-cholesten-3-one decreases breast cancer cell viability and alters membrane raft-localized EGFR expression by reducing lipogenesis and enhancing LXR-dependent cholesterol transporters. Lipids in health and disease. 2019 Sep; 18(1):168. doi: 10.1186/s12944-019-1103-7. [PMID: 31477154]
Leslie J Donato, Alan Lueke, Stacy M Kenyon, Jeffrey W Meeusen, Michael Camilleri. Description of analytical method and clinical utility of measuring serum 7-alpha-hydroxy-4-cholesten-3-one (7aC4) by mass spectrometry. Clinical biochemistry. 2018 Feb; 52(?):106-111. doi: 10.1016/j.clinbiochem.2017.10.008. [PMID: 29051033]
Chun-Lin Chen, Deng-Chyang Wu, Min-Yun Liu, Ming-Wei Lin, Hung-Tu Huang, Yaw-Bin Huang, Li-Chai Chen, Yu-Yu Chen, Jih-Jung Chen, Pei-Hua Yang, Yu-Chen Kao, Pei-Yu Chen. Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cells. Journal of receptor and signal transduction research. 2017 Apr; 37(2):189-199. doi: 10.1080/10799893.2016.1203944. [PMID: 27401208]
Marialena Mouzaki, Alice Y Wang, Robert Bandsma, Elena M Comelli, Bianca M Arendt, Ling Zhang, Scott Fung, Sandra E Fischer, Ian G McGilvray, Johane P Allard. Bile Acids and Dysbiosis in Non-Alcoholic Fatty Liver Disease. PloS one. 2016; 11(5):e0151829. doi: 10.1371/journal.pone.0151829. [PMID: 27203081]
Lijun Chen, Rui Zhan, Jinhe Jiang, Yan Zhang, Yi Dong, Yegao Chen. A new ent-kaurane diterpenoid from Ixora amplexicaulis. Natural product research. 2016; 30(1):105-9. doi: 10.1080/14786419.2015.1039000. [PMID: 25941744]
Sophie Bouvaine, Marie-Line Faure, Robert J Grebenok, Spencer T Behmer, Angela E Douglas. A dietary test of putative deleterious sterols for the aphid Myzus persicae. PloS one. 2014; 9(1):e86256. doi: 10.1371/journal.pone.0086256. [PMID: 24465993]
Matthew G K Benesch, David A Mannock, Ruthven N A H Lewis, Ronald N McElhaney. A DSC and FTIR spectroscopic study of the effects of the epimeric 4-cholesten-3-ols and 4-cholesten-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: comparison with their 5-cholesten analogues. Chemistry and physics of lipids. 2014 Jan; 177(?):71-90. doi: 10.1016/j.chemphyslip.2013.11.008. [PMID: 24296232]
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