InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8-,17-13+ |
FPIPGXGPPPQFEQ-MKOSUFFBSA-N |
C\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C |
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human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via retinol )
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View more via ChEBI Ontology
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
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IUPAC
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(9cis)-retinol
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IUPAC
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9-cis-retinol
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UniProt
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2054551
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Reaxys Registry Number
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Reaxys
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22737-97-9
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CAS Registry Number
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HMDB
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Paik J, Blaner WS, Swisshelm K (2005) Cis-retinol dehydrogenase: 9-cis-retinol metabolism and its effect on proliferation of human MCF7 breast cancer cells. Experimental cell research 303, 183-196 [PubMed:15572038] [show Abstract] 9-Cis-retinoic acid (RA) suppresses cancer cell proliferation via binding and activation of nuclear receptors, retinoid X receptors (RXRs). In vivo, 9-cis-RA is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH), an enzyme that we characterized previously. Since 9-cis-RA is a potent inhibitor of breast cancer cell proliferation, we hypothesized that overexpression of cRDH in breast cancer cells would result in increased production of 9-cis-RA, which in turn would suppress cell proliferation. To investigate this hypothesis, MCF7 human breast carcinoma cells were transduced with cRDH cDNA (LRDHSN/MCF7), and the growth kinetics and retinoid profiles of cells were examined following treatment with 9-cis-retinol. LRDHSN/MCF7 cells showed a marked reduction in cell numbers (60-80%) upon treatment with 9-cis-retinol compared to vehicle alone. Within 24 h of treatment, approximately 75% of the 9-cis-retinol was taken up and metabolized by LRDHSN/MCF7 cells. Despite the rapid uptake and oxidation of 9-cis-retinol to 9-cis-retinal, 9-cis-RA was not formed in these cells. We detect at least one novel metabolite formed from both 9-cis-retinol and 9-cis-retinal that may play a role in inhibition of MCF7 cell proliferation. Our studies demonstrate that 9-cis-retinol in combination with cRDH inhibits breast cancer cell proliferation by production of retinol metabolites other than RA. | Wolf G (2000) The oxidation of 9-cis-retinol: a possible synthesis pathway for 9-cis-retinoic acid. Nutrition reviews 58, 354-356 [PubMed:11140907] [show Abstract] A short-chain alcohol dehydrogenase has been discovered that oxidizes 9-cis- and 11-cis-retinol to their corresponding aldehydes. The gene for this enzyme was sequenced and appears to be expressed with highest efficiency in the retinal pigment epithelium of the eye, as well as in human liver and mammary gland and in mouse liver and kidney. Because 9-cis-retinol occurs in liver, it may be a precursor of 9-cis-retinoic acid. |
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