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Record Information
Version3.6
Creation Date2013-05-09 20:56:15 UTC
Update Date2016-02-11 07:59:57 UTC
HMDB IDHMDB60123
Secondary Accession NumbersNone
Metabolite Identification
Common Namerac-5,6-Epoxy-retinoyl-beta-D-glucuronide
DescriptionThis compound belongs to the family of Diterpene Glycosides. These are diterpenes in which an isoprene unit is glycosylated.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H36O9
Average Molecular Weight492.5586
Monoisotopic Molecular Weight492.23593275
IUPAC Name(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1/C26H36O9/c1-15(10-13-26-24(3,4)11-7-12-25(26,5)35-26)8-6-9-16(2)14-17(27)33-23-20(30)18(28)19(29)21(34-23)22(31)32/h6,8-10,13-14,18-21,23,28-30H,7,11-12H2,1-5H3,(H,31,32)/b9-6+,13-10+,15-8+,16-14+/t18-,19+,20-,21-,23-,25-,26-/s2
InChI KeyInChIKey=BZPOQLONXBJGAZ-NBUYDMCONA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Retinoid ester
  • Retinoid skeleton
  • Diterpenoid
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Oxepane
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
OriginNot Available
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 mg/mLALOGPS
logP3.14ALOGPS
logP2.83ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.05 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.82 m3·mol-1ChemAxon
Polarizability52.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60123
Metagene LinkHMDB60123
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]