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Record Information
Version1.0
Created at2022-09-05 21:15:24 UTC
Updated at2022-09-05 21:15:25 UTC
NP-MRD IDNP0220055
Secondary Accession NumbersNone
Natural Product Identification
Common Name(6s)-6-[(1s)-1-[(1s,3ar,3br,9ar,9bs,11as)-1,3a-dihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,8h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
Description(6S)-6-[(1S)-1-[(1S,2R,10R,11R,14S,15S)-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-5,7-dien-14-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-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. (6s)-6-[(1s)-1-[(1s,3ar,3br,9ar,9bs,11as)-1,3a-dihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,8h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one is found in Ajuga parviflora. Based on a literature review very few articles have been published on (6S)-6-[(1S)-1-[(1S,2R,10R,11R,14S,15S)-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-5,7-dien-14-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H38O7
Average Mass486.6050 Da
Monoisotopic Mass486.26175 Da
IUPAC Name(6S)-6-[(1S)-1-[(1S,2R,10R,11R,14S,15S)-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-14-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name(6S)-6-[(1S)-1-[(1S,2R,10R,11R,14S,15S)-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,7-dien-14-yl]-1-hydroxyethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
CAS Registry NumberNot Available
SMILES
CC1=C(CO)C(=O)O[C@@H](C1)[C@](C)(O)[C@]1(O)CC[C@@]2(O)[C@@H]3CC=C4C=CCC(=O)[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C28H38O7/c1-16-14-22(35-23(31)18(16)15-29)26(4,32)28(34)13-12-27(33)20-9-8-17-6-5-7-21(30)25(17,3)19(20)10-11-24(27,28)2/h5-6,8,19-20,22,29,32-34H,7,9-15H2,1-4H3/t19-,20+,22-,24-,25-,26-,27+,28-/m0/s1
InChI KeyBAIDVXUGHJDBOO-MXKUFHJFSA-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 parvifloraLOTUS 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
  • Withanolide-skeleton
  • 26-hydroxysteroid
  • 20-hydroxysteroid
  • 14-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Dihydropyranone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Enoate ester
  • Cyclic alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • 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
logP1.72ChemAxon
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity131.68 m³·mol⁻¹ChemAxon
Polarizability52.46 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 Compound163007687
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]