Showing metabocard for 13-cis Retinol (BMDB0006221)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:31 UTC
Update Date2020-04-22 15:16:58 UTC
BMDB IDBMDB0006221
Secondary Accession Numbers
  • BMDB06221
Metabolite Identification
Common Name13-cis Retinol
DescriptionVitamin 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13cis)-RetinolChEBI
(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-olChEBI
RETINOLChEBI
Neovitamin aKegg
(11-cis,13-cis)-Retinol acetateHMDB
11,13-Di-cis-vitamin a acetateHMDB
11-cis-13-cis-Retinol acetateHMDB
11-cis-13-cis-Retinyl acetateHMDB
Chemical FormulaC20H30O
Average Molecular Weight286.4516
Monoisotopic Molecular Weight286.229665582
IUPAC Name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional Name13-cis retinol
CAS Registry Number2052-63-3
SMILES
C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
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-
InChI KeyFPIPGXGPPPQFEQ-HWCYFHEPSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 m³·mol⁻¹ChemAxon
Polarizability36.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006221
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112229
KNApSAcK IDNot Available
Chemspider ID8079655
KEGG Compound IDC19962
BioCyc IDNot Available
BiGG ID2455099
Wikipedia LinkVitamin A
METLIN IDNot Available
PubChem Compound9904001
PDB IDNot Available
ChEBI ID45479
References
Synthesis ReferenceAlbert, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available