4-Hydroxyretinoic acid (BioDeep_00000011346)

 

Secondary id: BioDeep_00001874715

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid

化学式: C20H28O3 (316.2038)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 35.59%

分子结构信息

SMILES: C1C(C)(C)C(/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)=C(C)C(O)C1
InChI: InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

描述信息

4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384) [HMDB]
4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384).
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

25 个代谢物同义名

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; (2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid; (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; (2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate; 4-Hydroxy-(7E,9E,11E,13E)-retinoic acid; 4-Hydroxyretinoic acid, (13-cis)-isomer; (7E,9E,11E,13E)-4-Hydroxyretinoic acid; rac-4-Hydroxy-all-trans-retinoic acid; 4-Hydroxy-(7E,9E,11E,13E)-retinoate; (7E,9E,11E,13E)-4-Hydroxyretinoate; 4-Hydroxy-all-trans-retinoic acid; rac-4-Hydroxy-all-trans-retinoate; all-trans-4-hydroxyretinoic acid; 4-Hydroxy-13-cis-retinoic acid; 4-Hydroxy-all-trans-retinoate; all-trans-4-Hydroxyretinoate; 4-Hydroxy-13-retinoic acid; 4-Hydroxy-13-cis-retinoate; 4-Hydroxy-retinoic acid; 4-Hydroxyretinoic acid; 4-Hydroxy-retinoate; 4-Hydroxyretinoate; 4-OH-Retinoic acid; 4-OH-Retinoate



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(10)

BioCyc(0)

PlantCyc(0)

代谢反应

137 个相关的代谢反应过程信息。

Reactome(127)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(9)

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 12 ALB, CASP3, CYP1A1, CYP2C18, CYP2C8, CYP2C9, CYP3A4, MARVELD1, PML, RARA, RARB, RARG
Peripheral membrane protein 3 CYP1A1, HSD17B6, PML
Endoplasmic reticulum membrane 10 CYP1A1, CYP26A1, CYP2C18, CYP2C8, CYP2C9, CYP3A4, CYP3A5, CYP3A7, PML, UGT2B7
Nucleus 7 ALB, CASP3, MARVELD1, PML, RARA, RARB, RARG
cytosol 4 ALB, CASP3, PML, RARA
dendrite 1 RARA
centrosome 1 ALB
nucleoplasm 5 CASP3, PML, RARA, RARB, RARG
RNA polymerase II transcription regulator complex 1 RARA
Cell membrane 2 CLDN1, MARVELD1
Cytoplasmic side 1 PML
Early endosome membrane 2 HSD17B6, PML
Multi-pass membrane protein 2 CLDN1, MARVELD1
cell surface 1 ITGAX
glutamatergic synapse 1 CASP3
Golgi apparatus 1 ALB
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 CASP3
plasma membrane 8 CLDN1, CYP2C18, CYP2C8, CYP2C9, ITGAX, MARVELD1, PRAM1, RARA
Membrane 7 CLDN1, CYP3A4, CYP3A5, ITGAX, MARVELD1, RARG, UGT2B7
apical plasma membrane 1 CLDN1
basolateral plasma membrane 1 CLDN1
extracellular exosome 1 ALB
Lumenal side 1 HSD17B6
endoplasmic reticulum 2 ALB, HSD17B6
extracellular space 1 ALB
perinuclear region of cytoplasm 1 RARA
Cell junction, tight junction 1 CLDN1
bicellular tight junction 1 CLDN1
mitochondrion 1 CYP1A1
protein-containing complex 4 ALB, CLDN1, PRAM1, RARA
intracellular membrane-bounded organelle 7 CYP1A1, CYP2C18, CYP2C8, CYP2C9, CYP3A4, CYP3A5, HSD17B6
Microsome membrane 8 CYP1A1, CYP26A1, CYP2C18, CYP2C9, CYP3A4, CYP3A5, CYP3A7, HSD17B6
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 ITGAX
Secreted 1 ALB
extracellular region 1 ALB
Single-pass membrane protein 1 UGT2B7
anchoring junction 1 ALB
transcription regulator complex 2 RARA, RARG
nuclear membrane 1 PML
external side of plasma membrane 1 ITGAX
actin cytoskeleton 1 RARA
nucleolus 2 PML, RARA
Mitochondrion inner membrane 1 CYP1A1
Cytoplasm, cytoskeleton 1 MARVELD1
Nucleus, PML body 1 PML
PML body 1 PML
lateral plasma membrane 1 CLDN1
ciliary basal body 1 ALB
chromatin 3 RARA, RARB, RARG
cytoskeleton 1 MARVELD1
centriole 1 ALB
spindle pole 1 ALB
chromosome, telomeric region 1 PML
blood microparticle 1 ALB
Basolateral cell membrane 1 CLDN1
tertiary granule membrane 1 ITGAX
secretory granule membrane 1 ITGAX
endoplasmic reticulum lumen 1 ALB
nuclear matrix 1 PML
platelet alpha granule lumen 1 ALB
tight junction 1 CLDN1
ficolin-1-rich granule membrane 1 ITGAX
death-inducing signaling complex 1 CASP3
integrin complex 1 ITGAX
integrin alphaX-beta2 complex 1 ITGAX
ciliary transition fiber 1 ALB


文献列表

  • James V Chithalen, Luong Luu, Martin Petkovich, Glenville Jones. HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A. Journal of lipid research. 2002 Jul; 43(7):1133-42. doi: 10.1194/jlr.m100343-jlr200. [PMID: 12091498]
  • M Ahmad, M Ahmadi, P J Nicholls, H J Smith. In-vitro metabolism of retinoic acid by different tissues from male rats. The Journal of pharmacy and pharmacology. 2000 May; 52(5):511-5. doi: 10.1211/0022357001774291. [PMID: 10864138]
  • V M Samokyszyn, W E Gall, G Zawada, M A Freyaldenhoven, G Chen, P I Mackenzie, T R Tephly, A Radominska-Pandya. 4-hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7. The Journal of biological chemistry. 2000 Mar; 275(10):6908-14. doi: 10.1074/jbc.275.10.6908. [PMID: 10702251]
  • P A Spear, H Garcin, J F Narbonne. Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. Canadian journal of physiology and pharmacology. 1988 Sep; 66(9):1181-6. doi: 10.1139/y88-194. [PMID: 2851384]