Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2022-09-05 23:12:10 UTC
Updated at2022-09-05 23:12:10 UTC
NP-MRD IDNP0221581
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-(2-{3a,7,8-trihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1,2-dihydroxypropyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one
Description5-(1,2-Dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. 5-(2-{3a,7,8-trihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1,2-dihydroxypropyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one is found in Ajuga reptans. 5-(1,2-Dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H44O9
Average Mass536.6620 Da
Monoisotopic Mass536.29853 Da
IUPAC Name5-(1,2-dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one
Traditional Name5-(1,2-dihydroxy-2-{4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-14-yl}propyl)-4-ethyl-4-hydroxy-3-methyloxolan-2-one
CAS Registry NumberNot Available
SMILES
CCC1(O)C(C)C(=O)OC1C(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C29H44O9/c1-6-28(36)14(2)24(34)38-23(28)22(33)27(5,35)21-8-10-29(37)16-11-18(30)17-12-19(31)20(32)13-25(17,3)15(16)7-9-26(21,29)4/h11,14-15,17,19-23,31-33,35-37H,6-10,12-13H2,1-5H3
InChI KeyJWAUYPGAZQEFKS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ajuga reptansLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Hexahydroxy bile acid, alcohol, or derivatives
  • Withanolide-skeleton
  • Ecdysteroid
  • 24-hydroxysteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • 20-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 6-oxosteroid
  • 2-hydroxysteroid
  • 14-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Cyclohexenone
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Ketone
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • 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
logP1.29ALOGPS
logP0.49ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.67ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity136.97 m³·mol⁻¹ChemAxon
Polarizability57.25 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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 Compound74932721
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]