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Record Information
Version2.0
Created at2022-09-06 22:59:43 UTC
Updated at2022-09-06 22:59:43 UTC
NP-MRD IDNP0239401
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
Description9-(Hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid is found in Aralia armata, Caryocar glabrum, Eleutherococcus senticosus and Medicago hybrida. 9-(Hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
9-(Hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylateGenerator
Chemical FormulaC37H58O10
Average Mass662.8610 Da
Monoisotopic Mass662.40300 Da
IUPAC Name9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
Traditional Name9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC(=O)C1OC(OC2CCC3(C)C(CCC4(C)C3CC=C3C5CC(C)(C)CCC5(CCC43C)C(O)=O)C2(C)CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C37H58O10/c1-32(2)14-16-37(31(43)44)17-15-35(5)20(21(37)18-32)8-9-23-33(3)12-11-24(34(4,19-38)22(33)10-13-36(23,35)6)46-30-27(41)25(39)26(40)28(47-30)29(42)45-7/h8,21-28,30,38-41H,9-19H2,1-7H3,(H,43,44)
InChI KeyNYWHIGQIORRJMF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aralia armataLOTUS Database
Caryocar glabrumLOTUS Database
Eleutherococcus senticosusLOTUS Database
Medicago hybridaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • Steroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Methyl ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Acetal
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP4.5ALOGPS
logP4.01ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity172.45 m³·mol⁻¹ChemAxon
Polarizability74.18 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14020473
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]