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Record Information
Version2.0
Created at2022-09-06 22:21:13 UTC
Updated at2022-09-06 22:21:13 UTC
NP-MRD IDNP0238874
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3ar,5as,6s,7s,9as,9br,11ar)-1-[(2r,3e,5s)-5-isopropyl-6-methylhepta-3,6-dien-2-yl]-6,9a,11a-trimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
Description(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5S)-6-methyl-5-(propan-2-yl)hepta-3,6-dien-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (1r,3ar,5as,6s,7s,9as,9br,11ar)-1-[(2r,3e,5s)-5-isopropyl-6-methylhepta-3,6-dien-2-yl]-6,9a,11a-trimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Viola reichenbachiana. Based on a literature review very few articles have been published on (1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5S)-6-methyl-5-(propan-2-yl)hepta-3,6-dien-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-ol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H50O
Average Mass438.7400 Da
Monoisotopic Mass438.38617 Da
IUPAC Name(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5S)-6-methyl-5-(propan-2-yl)hepta-3,6-dien-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,6S,7S,11R,14R,15R)-14-[(2R,3E,5S)-5-isopropyl-6-methylhepta-3,6-dien-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@@H](\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)=C
InChI Identifier
InChI=1S/C31H50O/c1-19(2)23(20(3)4)10-9-21(5)25-13-14-27-24-11-12-26-22(6)29(32)16-18-31(26,8)28(24)15-17-30(25,27)7/h9-11,20-23,25-29,32H,1,12-18H2,2-8H3/b10-9+/t21-,22+,23+,25-,26+,27+,28+,29+,30-,31+/m1/s1
InChI KeyMIMFGBDIMNNWHS-YPXXWRHSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Viola reichenbachianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP7.79ChemAxon
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.68 m³·mol⁻¹ChemAxon
Polarizability56.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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 Compound163076183
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]