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Record Information
Version2.0
Created at2022-09-12 01:06:08 UTC
Updated at2022-09-12 01:06:08 UTC
NP-MRD IDNP0322368
Secondary Accession NumbersNone
Natural Product Identification
Common Name(6r)-6-{1-[(1z,2s,3as,3bs,6s,9ar,9bs,11as)-2,6-dihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-ylidene]ethyl}-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
Description(22R)-4beta,16beta,27-Trihydroxy-22,26-epoxyergosta-2,5,17(20),24-tetraene-1,26-dione belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (6r)-6-{1-[(1z,2s,3as,3bs,6s,9ar,9bs,11as)-2,6-dihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-ylidene]ethyl}-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one is found in Withania aristata. Based on a literature review very few articles have been published on (22R)-4beta,16beta,27-Trihydroxy-22,26-epoxyergosta-2,5,17(20),24-tetraene-1,26-dione.
Structure
Thumb
Synonyms
ValueSource
(22R)-4b,16b,27-Trihydroxy-22,26-epoxyergosta-2,5,17(20),24-tetraene-1,26-dioneGenerator
(22R)-4Β,16β,27-trihydroxy-22,26-epoxyergosta-2,5,17(20),24-tetraene-1,26-dioneGenerator
Chemical FormulaC28H36O6
Average Mass468.5900 Da
Monoisotopic Mass468.25119 Da
IUPAC Name(6R)-6-{1-[(1S,2R,6S,10S,11S,13S,14Z,15S)-6,13-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,7-dien-14-ylidene]ethyl}-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name(6R)-6-{1-[(1S,2R,6S,10S,11S,13S,14Z,15S)-6,13-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,7-dien-14-ylidene]ethyl}-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
CAS Registry NumberNot Available
SMILES
C\C([C@H]1CC(C)=C(CO)C(=O)O1)=C1\[C@@H](O)C[C@H]2[C@@H]3CC=C4[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C28H36O6/c1-14-11-23(34-26(33)17(14)13-29)15(2)25-22(31)12-20-16-5-6-19-21(30)7-8-24(32)28(19,4)18(16)9-10-27(20,25)3/h6-8,16,18,20-23,29-31H,5,9-13H2,1-4H3/b25-15+/t16-,18+,20+,21+,22+,23-,27+,28-/m1/s1
InChI KeyGPNLSEVBFOXDFF-GUBMYHPBSA-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
Withania aristataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Steroid lactone
  • Androstane-skeleton
  • 4-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • 16-beta-hydroxysteroid
  • 16-hydroxysteroid
  • Cyclohexenone
  • Dihydropyranone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen 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
logP2.49ChemAxon
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity130.84 m³·mol⁻¹ChemAxon
Polarizability52.01 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 Compound46939432
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]