1.0 2016-09-30 23:20:31 UTC 2020-04-22 15:16:58 UTC BMDB0006221 BMDB06221 13-cis Retinol Vitamin a, also known as (13cis)-retinol, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, vitamin a is considered to be an isoprenoid lipid molecule. Vitamin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Vitamin a exists in all living organisms, ranging from bacteria to humans. Vitamin a participates in a number of enzymatic reactions, within cattle. In particular, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme diacylglycerol O-acyltransferase 1. In addition, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme acyl-CoA wax alcohol acyltransferase 1. In cattle, vitamin a is involved in the metabolic pathway called the retinol metabolism pathway. Vitamin a is a potentially toxic compound. Vitamin a has been found to be associated with several diseases known as pregnancy, hemodialysis, and thyroid cancer; also vitamin a has been linked to the inborn metabolic disorders including abetalipoproteinemia. (13cis)-Retinol (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol RETINOL Neovitamin a (11-cis,13-cis)-Retinol acetate 11,13-Di-cis-vitamin a acetate 11-cis-13-cis-Retinol acetate 11-cis-13-cis-Retinyl acetate C20H30O 286.4516 286.229665582 (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol 13-cis retinol 2052-63-3 C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C 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-HWCYFHEPSA-N belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Retinoids Diterpenoids Fatty alcohols Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic homomonocyclic compound Diterpenoid Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Retinoid skeleton Aliphatic homomonocyclic compounds Retinoids retinol Solid logp 6.38 ALOGPS logs -4.58 ALOGPS logp 4.69 ChemAxon pka_strongest_acidic 16.44 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol ChemAxon average_mass 286.4516 ChemAxon mono_mass 286.229665582 ChemAxon smiles C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C20H30O ChemAxon inchi 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- ChemAxon inchikey FPIPGXGPPPQFEQ-HWCYFHEPSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 97.92 ChemAxon polarizability 36.28 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Retinol Metabolism SMP0087260 Specdb::EiMs 1998 Specdb::NmrTwoD 2027 Specdb::CMs 21999 Specdb::CMs 38969 Specdb::CMs 174214 Specdb::MsMs 314854 Specdb::MsMs 314855 Specdb::MsMs 314856 Specdb::MsMs 360676 Specdb::MsMs 360677 Specdb::MsMs 360678 Specdb::MsMs 1218230 Specdb::MsMs 1218231 Specdb::MsMs 1218232 Specdb::MsMs 2702691 Specdb::MsMs 2702692 Specdb::MsMs 2702693 Specdb::MsMs 3002209 Specdb::MsMs 3002210 Specdb::MsMs 3002211 FDB112229 8079655 9904001 45479 C19962 2455099 Vitamin A Albert, Klaus; Schlotterbeck, Goetz; Braumann, Ulrich; Haendel, Heidrun; Spraul, Manfred; Krack, Gerhard. Structure determination of vitamin A acetate isomers through coupled HPLC and 1H NMR spectroscopy. Angewandte Chemie, International Edition in English (1995), 34(9), 1014-16.