Vitamin A2 (BioDeep_00000023341)
Secondary id: BioDeep_00000015263, BioDeep_00000598401
human metabolite Endogenous
代谢物信息卡片
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-ol
化学式: C20H28O (284.2140038)
中文名称:
谱图信息:
最多检出来源 Viridiplantae(plant) 1.14%
分子结构信息
SMILES: C/C(=C\C=C\C(=C\CO)\C)/C=C/C1=C(C)C=CCC1(C)C
InChI: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,21H,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
描述信息
Vitamin A2 is the form, C20H28O, of vitamin A found in the retina and liver of freshwater fishes and certain invertebrates and amphibians; it differs from retinol (vitamin A1) in having one more conjugated double bond and has approximately one-third the biological activity of retinol. Called also retinol2.
Constituent of fresh-water fish oils. 3,4-Didehydroretinol is found in fats and oils and fishes.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
同义名列表
15 个代谢物同义名
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-ol; 3,4-Didehydro-all-trans-retinol; All-Trans-3,4-Didehydro Retinol; all-trans-3,4-Didehydroretinol; Vitamin a2, (7-cis)-isomer; all-trans-3-Dehydroretinol; 3,4-Didehydro retinol; 3,4-didehydro-retinol; 3,4-Didehydroretinol; 3-Dehydroretinol; 3-Dehydoretinol; Dehydroretinol; vitamin A 2; Vitamin A2; VA2
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:132246
- KEGG: C21797
- PubChem: 6436043
- PubChem: 65722
- HMDB: HMDB0013117
- ChEMBL: CHEMBL1797132
- Wikipedia: Dehydroretinal
- MetaCyc: CPD-20073
- KNApSAcK: C00044897
- foodb: FDB013830
- chemspider: 4940721
- CAS: 79-80-1
- PMhub: MS000107148
- LipidMAPS: LMPR01090008
- RefMet: All-trans-3,4-didehydro retinol
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。
文献列表
- Kentaro Ueda, Fumiko Akashi, Motoki Kawasaki, Tatsuya Sugawara, Yuki Manabe, Tohru Matsui. Effects of feeding on plasma concentrations of vitamin A in captive African penguins (Spheniscus demersus).
The Journal of veterinary medical science.
2019 Nov; 81(11):1580-1585. doi:
10.1292/jvms.19-0316. [PMID: 31548472] - Catherine Landry, Magali Houde, Philippe Brodeur, Philip Spear, Monique Boily. Lipophilic antioxidants and lipid peroxidation in yellow perch subjected to various anthropogenic influences along the St. Lawrence River (QC, Canada).
Ecotoxicology and environmental safety.
2017 May; 139(?):316-325. doi:
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Journal of animal physiology and animal nutrition.
2012 Dec; 96(6):1044-53. doi:
10.1111/j.1439-0396.2011.01219.x. [PMID: 21895779] - Michel A Defo, Fabien Pierron, Philip A Spear, Louis Bernatchez, Peter G C Campbell, Patrice Couture. Evidence for metabolic imbalance of vitamin A2 in wild fish chronically exposed to metals.
Ecotoxicology and environmental safety.
2012 Nov; 85(?):88-95. doi:
10.1016/j.ecoenv.2012.08.017. [PMID: 22959581] - Anne L Escaron, Michael H Green, Sherry A Tanumihardjo. Plasma turnover of 3,4-didehydroretinol (vitamin A2) increases in vitamin A-deficient rats fed low versus high dietary fat.
Journal of lipid research.
2009 Apr; 50(4):694-703. doi:
10.1194/jlr.m800479-jlr200. [PMID: 19043141] - Emmanuel M Kafwembe, James Chipipa, Eric Njunju, Roma Chilengi. The vitamin A status of Zambian children in a community of vitamin A supplementation and sugar fortification strategies as measured by the modified relative dose response (MRDR) test.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
2009 Jan; 79(1):40-7. doi:
10.1024/0300-9831.79.1.40. [PMID: 19839002] - Ting Sun, Rebecca L Surles, Sherry A Tanumihardjo. Vitamin A concentrations in piglet extrahepatic tissues respond differently ten days after vitamin A treatment.
The Journal of nutrition.
2008 Jun; 138(6):1101-6. doi:
10.1093/jn/138.6.1101. [PMID: 18492841] - Alexander R Moise, Andrea Isken, Marta Domínguez, Angel R de Lera, Johannes von Lintig, Krzysztof Palczewski. Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8- dihydroretinol.
Biochemistry.
2007 Feb; 46(7):1811-20. doi:
10.1021/bi062147u. [PMID: 17253779] - Rebecca L Surles, Jialiang Li, Sherry A Tanumihardjo. The modified-relative-dose-response values in serum and milk are positively correlated over time in lactating sows with adequate vitamin A status.
The Journal of nutrition.
2006 Apr; 136(4):939-45. doi:
10.1093/jn/136.4.939. [PMID: 16549454] - Anne Käkelä, Reijo Käkelä, Heikki Hyvärinen. Importance of the kidneys in metabolism of vitamins A1 and A2 and their fatty acyl esters in mink feeding on fish-based diets and exposed to Aroclor 1242.
Toxicology and applied pharmacology.
2003 Mar; 187(2):118-27. doi:
10.1016/s0041-008x(02)00067-4. [PMID: 12649044] - Anne Käkelä, Reijo Käkelä, Heikki Hyvärinen, Petteri Nieminen. Effects of Aroclor 1242 and different fish-based diets on vitamins A1 (retinol) and A2 (3,4-didehydroretinol), and their fatty acyl esters in mink plasma.
Environmental research.
2003 Feb; 91(2):104-12. doi:
10.1016/s0013-9351(02)00014-2. [PMID: 12584011] - Anne Käkelä, Reijo Käkelä, Heikki Hyvärinen, Juha Asikainen. Vitamins A1 and A2 in hepatic tissue and subcellular fractions in mink feeding on fish-based diets and exposed to Aroclor 1242.
Environmental toxicology and chemistry.
2002 Feb; 21(2):397-403. doi:
". [PMID: 11833811] - Sherry A Tanumihardjo, Kristina L Penniston. Simplified methodology to determine breast milk retinol concentrations.
Journal of lipid research.
2002 Feb; 43(2):350-5. doi:
10.1016/s0022-2275(20)30178-4. [PMID: 11861678] - S de Pee, Y Yuniar, C E West, Muhilal. Evaluation of biochemical indicators of vitamin A status in breast-feeding and non-breast-feeding Indonesian women.
The American journal of clinical nutrition.
1997 Jul; 66(1):160-7. doi:
10.1093/ajcn/66.1.160. [PMID: 9209185] - E M Kafwembe, T Y Sukwa, C Manyando, D Mwandu, J Chipipa, P Chipaila. The vitamin A status of Zambian children attending an under five clinic as evaluated by the modified relative dose response (MRDR) test.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
1996; 66(3):190-6. doi:
NULL. [PMID: 8899450] - S A Tanumihardjo, Muherdiyantiningsih, D Permaesih, Komala, Muhilal, D Karyadi, J A Olson. Daily supplements of vitamin A (8.4 mumol, 8000 IU) improve the vitamin A status of lactating Indonesian women.
The American journal of clinical nutrition.
1996 Jan; 63(1):32-5. doi:
10.1093/ajcn/63.1.32. [PMID: 8604666] - R K Randolph, M Simon. all-trans-retinoic acid regulates retinol and 3,4-didehydroretinol metabolism in cultured human epidermal keratinocytes.
The Journal of investigative dermatology.
1996 Jan; 106(1):168-75. doi:
10.1111/1523-1747.ep12329900. [PMID: 8592069] - M A Wahed, J O Alvarez, M A Khaled, D Mahalanabis, M M Rahman, D Habte. Comparison of the modified relative dose response (MRDR) and the relative dose response (RDR) in the assessment of vitamin A status in malnourished children.
The American journal of clinical nutrition.
1995 Jun; 61(6):1253-6. doi:
10.1093/ajcn/61.6.1253. [PMID: 7762526] - E Andersson, C Björklind, H Törmä, A Vahlquist. The metabolism of vitamin A to 3,4-didehydroretinol can be demonstrated in human keratinocytes, melanoma cells and HeLa cells, and is correlated to cellular retinoid-binding protein expression.
Biochimica et biophysica acta.
1994 Dec; 1224(3):349-54. doi:
10.1016/0167-4889(94)90267-4. [PMID: 7803489] - S A Tanumihardjo, Muherdiyantiningsih, D Permaesih, A M Dahro, Muhilal, D Karyadi, J A Olson. Assessment of the vitamin A status in lactating and nonlactating, nonpregnant Indonesian women by use of the modified-relative-dose-response (MRDR) test.
The American journal of clinical nutrition.
1994 Jul; 60(1):142-7. doi:
10.1093/ajcn/60.1.142. [PMID: 8017329] - O Rollman, E J Wood, M J Olsson, W J Cunliffe. Biosynthesis of 3,4-didehydroretinol from retinol by human skin keratinocytes in culture.
The Biochemical journal.
1993 Aug; 293 ( Pt 3)(?):675-82. doi:
10.1042/bj2930675. [PMID: 8352734] - M Azuma, T Irie, T Seki. Retinals and retinols induced by estrogen in the blood plasma of Xenopus laevis.
The Journal of experimental biology.
1993 May; 178(?):89-96. doi:
10.1242/jeb.178.1.89. [PMID: 8315372] - S A Tanumihardjo, P G Koellner, J A Olson. The modified relative-dose-response assay as an indicator of vitamin A status in a population of well-nourished American children.
The American journal of clinical nutrition.
1990 Dec; 52(6):1064-7. doi:
10.1093/ajcn/52.6.1064. [PMID: 2239782] - A T Tsin, S N Gentles, E A Castillo. Selective utilization of serum vitamin A for visual pigment synthesis.
The Journal of experimental biology.
1989 Mar; 142(?):207-14. doi:
10.1242/jeb.142.1.207. [PMID: 2723579] - S A Tanumihardjo, J A Olson. A modified relative dose-response assay employing 3,4-didehydroretinol (vitamin A2) in rats.
The Journal of nutrition.
1988 May; 118(5):598-603. doi:
10.1093/jn/118.5.598. [PMID: 3367238] - S A Tanumihardjo, A B Barua, J A Olson. Use of 3,4-didehydroretinol to assess vitamin A status in rats.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
1987; 57(2):127-32. doi:
NULL. [PMID: 3654104] - H Törmä, A Vahlquist. Biosynthesis of 3-dehydroretinol (vitamin A2) from all-trans-retinol (vitamin A1) in human epidermis.
The Journal of investigative dermatology.
1985 Dec; 85(6):498-500. doi:
10.1111/1523-1747.ep12277290. [PMID: 4067325] - O Rollman, A Vahlquist. Vitamin A in skin and serum--studies of acne vulgaris, atopic dermatitis, ichthyosis vulgaris and lichen planus.
The British journal of dermatology.
1985 Oct; 113(4):405-13. doi:
10.1111/j.1365-2133.1985.tb02354.x. [PMID: 2933053] - O Rollman, A Vahlquist. Psoriasis and vitamin A. Plasma transport and skin content of retinol, dehydroretinol and carotenoids in adult patients versus healthy controls.
Archives of dermatological research.
1985; 278(1):17-24. doi:
10.1007/bf00412490. [PMID: 4096526] - B Berne, A Vahlquist, T Fischer, B G Danielson, C Berne. UV treatment of uraemic pruritus reduces the vitamin A content of the skin.
European journal of clinical investigation.
1984 Jun; 14(3):203-6. doi:
10.1111/j.1365-2362.1984.tb01124.x. [PMID: 6432548] - R HIROBE, T MIKAWA. [Influence of rice- or wheat-feeding on the urinary excretion of vitamin C. 2. Experiment in guinea pigs and human beings].
Rodo kagaku. The Journal of science of labour.
1962 Jun; 38(?):352-5. doi:
NULL. [PMID: 13907652] - M M ABDULLAH, S R MORCOS, M K SALAH. Content of vitamin A2 in some Nile fishes.
The Biochemical journal.
1954 Apr; 56(4):569-71. doi:
10.1042/bj0560569. [PMID: 13159882] - E M SHANTZ, N D EMBREE. The replacement of vitamin A1 by vitamin A2 in the retina of the rat.
The Journal of biological chemistry.
1946 May; 163(?):455-64. doi:
". [PMID: 21024915] - E M SHANTZ, N D EMBREE. Replacement of vitamin A1 by vitamin A2 in the retina of the rat.
Federation proceedings.
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". [PMID: 21066771]