4-oxo-Retinoic acid (BioDeep_00000019605)

 

Secondary id: BioDeep_00000011347, BioDeep_00001874726

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

化学式: C20H26O3 (314.1882)
中文名称: 4-氧代-维A酸, 4 - 氧代视黄酸
谱图信息: 最多检出来源 Homo sapiens(blood) 46.39%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

4-oxo-Retinoic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-oxo-retinoic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000019605). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

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/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

描述信息

4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545) [HMDB]
4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545).
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
all-trans-4-Oxoretinoic acid, an active metabolite of vitamin A, induces gene transcription via binding to nuclear retinoic acid receptors (RARs).

同义名列表

22 个代谢物同义名

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; 4-Oxoretinoic acid, (13-cis)-isomer; all-trans 4-Keto Retinoic Acid; 4-oxo-all-trans-Retinoic acid; all-trans-4-Oxoretinoic acid; 4-oxo-13-cis-Retinoic acid; 4-oxo-all-trans-Retinoate; 4-oxo-trans-Retinoic acid; all-trans-4-Oxoretinoate; 4-Keto-retinoic acid; 4-oxo-Retinoic acid; 4-Ketoretinoic acid; 4-Oxoretinoic acid; 4-oxo-Isotretinoin; 4-Keto-retinoate; 4-oxo-Retinoate; 4-Ketoretinoate; 4-Oxotretinoin; 4-Oxoretinoate; Ro 12-4824; Ro 11-4824; 4-oxo-AtRA



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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 11 ALDH1A1, CRABP1, CYP1A1, CYP26B1, GJA1, ODC1, PML, RARA, RARB, RARG, RXRA
Peripheral membrane protein 4 CYP1A1, CYP26B1, HSD17B6, PML
Endoplasmic reticulum membrane 8 CYP1A1, CYP26A1, CYP26B1, CYP26C1, GJA1, LRAT, PML, RAC2
Nucleus 8 CRABP1, GJA1, PML, RARA, RARB, RARG, RBP2, RXRA
cytosol 9 ALDH1A1, CRABP1, GJA1, ODC1, PML, RAC2, RARA, RBP2, RXRA
dendrite 1 RARA
nucleoplasm 7 GJA1, PML, RARA, RARB, RARG, RBP2, RXRA
RNA polymerase II transcription regulator complex 2 RARA, RXRA
Cell membrane 2 GJA1, RBP2
Cytoplasmic side 1 PML
lamellipodium 1 RAC2
Cell projection, axon 1 ALDH1A1
Early endosome membrane 2 HSD17B6, PML
Multi-pass membrane protein 1 GJA1
Synapse 2 ALDH1A1, RBP2
cell junction 1 GJA1
cell surface 1 ITGAX
Golgi apparatus 1 GJA1
Golgi membrane 1 GJA1
mitochondrial inner membrane 1 CYP1A1
Cytoplasm, cytosol 1 ALDH1A1
plasma membrane 6 GJA1, ITGAX, PRAM1, RAC2, RARA, RBP2
Membrane 3 CYP26C1, ITGAX, RARG
apical plasma membrane 1 GJA1
axon 1 ALDH1A1
extracellular exosome 3 ALDH1A1, RAC2, RBP4
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 GJA1, HSD17B6, LRAT
extracellular space 1 RBP4
perinuclear region of cytoplasm 2 LRAT, RARA
gap junction 1 GJA1
intercalated disc 1 GJA1
mitochondrion 3 CYP1A1, GJA1, RXRA
protein-containing complex 2 PRAM1, RARA
intracellular membrane-bounded organelle 3 CYP1A1, GJA1, HSD17B6
Microsome membrane 4 CYP1A1, CYP26A1, CYP26B1, HSD17B6
Single-pass type I membrane protein 1 ITGAX
Secreted 1 RBP4
extracellular region 1 RBP4
Single-pass membrane protein 2 CYP26C1, LRAT
mitochondrial outer membrane 1 RAC2
transcription regulator complex 3 RARA, RARG, RXRA
nuclear membrane 1 PML
external side of plasma membrane 1 ITGAX
Endosome, multivesicular body 1 LRAT
multivesicular body 1 LRAT
actin cytoskeleton 1 RARA
nucleolus 3 PML, RARA, RBP2
Cytoplasm, perinuclear region 1 LRAT
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 GJA1
focal adhesion 2 GJA1, RAC2
Nucleus, PML body 1 PML
PML body 1 PML
Cell junction, gap junction 1 GJA1
connexin complex 1 GJA1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 1 GJA1
receptor complex 1 RXRA
chromatin 5 RARA, RARB, RARG, RBP2, RXRA
phagocytic vesicle membrane 1 RAC2
Nucleus, nucleolus 1 RBP2
chromosome, telomeric region 1 PML
nuclear envelope 1 RAC2
tertiary granule membrane 1 ITGAX
Golgi-associated vesicle membrane 1 GJA1
secretory granule membrane 1 ITGAX
nuclear matrix 1 PML
tight junction 1 GJA1
protein-DNA complex 1 RBP2
ficolin-1-rich granule membrane 1 ITGAX
Rough endoplasmic reticulum 1 LRAT
integrin complex 1 ITGAX
cell-cell contact zone 1 GJA1
NADPH oxidase complex 1 RAC2
integrin alphaX-beta2 complex 1 ITGAX


文献列表

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  • Olivier Sorg, Christian Tran, Pierre Carraux, Denise Grand, Christelle Barraclough, Jean-François Arrighi, Patrick Descombes, Vincent Piguet, Jean-Hilaire Saurat. Metabolism and biological activities of topical 4-oxoretinoids in mouse skin. The Journal of investigative dermatology. 2008 Apr; 128(4):999-1008. doi: 10.1038/sj.jid.5701106. [PMID: 17943179]
  • Thomas E Gundersen, Nasser E Bastani, Rune Blomhoff. Quantitative high-throughput determination of endogenous retinoids in human plasma using triple-stage liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2007; 21(7):1176-86. doi: 10.1002/rcm.2946. [PMID: 17330217]
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