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Record Information
Version2.0
Created at2022-09-06 22:46:40 UTC
Updated at2022-09-06 22:46:40 UTC
NP-MRD IDNP0239230
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(1s,5r)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]oxy}oxane-3,4,5-triol
Description(-)-Trans-Carveol glucoside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone (-)-trans-Carveol glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-trans-Carveol glucoside has been detected, but not quantified in, citrus. (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(1s,5r)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]oxy}oxane-3,4,5-triol is found in Mentha spicata. This could make (-)-trans-carveol glucoside a potential biomarker for the consumption of these foods.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H26O6
Average Mass314.3740 Da
Monoisotopic Mass314.17294 Da
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]oxy}oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]oxy}oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CC(=C)[C@@H]1CC=C(C)[C@H](C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H26O6/c1-8(2)10-5-4-9(3)11(6-10)21-16-15(20)14(19)13(18)12(7-17)22-16/h4,10-20H,1,5-7H2,2-3H3/t10-,11+,12-,13-,14+,15-,16-/m1/s1
InChI KeyIPOIBBMZOXJYFV-RMPHEQRESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mentha spicataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • P-menthane monoterpenoid
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP-0.04ALOGPS
logP0.22ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.41 m³·mol⁻¹ChemAxon
Polarizability33.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029848
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001068
KNApSAcK IDNot Available
Chemspider ID8885718
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10710378
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]