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Record Information
Version2.0
Created at2024-05-03 03:51:40 UTC
Updated at2024-09-03 04:20:49 UTC
NP-MRD IDNP0332981
Natural Product DOIhttps://doi.org/10.57994/2262
Secondary Accession NumbersNone
Natural Product Identification
Common NameWithastramonolide A
DescriptionWithastramonolide A 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. Withastramonolide A was first documented in 2024 (PMID: 38084071). Based on a literature review very few articles have been published on Withastramonolide A.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC43H54O12
Average Mass762.8930 Da
Monoisotopic Mass762.36153 Da
IUPAC Name[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)C(O)[C@H]2O)C(=O)O1
InChI Identifier
InChI=1S/C43H54O12/c1-22-18-32(23(2)28-13-14-29-36-30(16-17-42(28,29)3)43(4)25(19-31(36)45)6-5-7-34(43)46)54-40(51)27(22)20-53-41-39(50)38(49)37(48)33(55-41)21-52-35(47)15-10-24-8-11-26(44)12-9-24/h5,7-12,15,19,23,28-33,36-39,41,44-45,48-50H,6,13-14,16-18,20-21H2,1-4H3/b15-10+/t23-,28+,29-,30-,31+,32+,33+,36-,37+,38?,39+,41+,42+,43-/m0/s1
InChI KeyXLHUMJNCPFKSNR-PPOKXSMESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)570075670@qq.com黑龙江中医药大学Pan juan2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
stramonium
      Not Available
Chemical Taxonomy
DescriptionThis compound 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
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Steroid ester
  • Diterpenoid
  • Diterpene lactone
  • Saccharolipid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • Hydroxysteroid
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Coumaric acid ester
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Fatty alcohol ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Alkyl glycoside
  • Quinomethane
  • M-quinomethane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Phenol
  • Dihydropyranone
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated ketone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Enone
  • Acryloyl-group
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP4.97ChemAxon
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.28 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity202.86 m³·mol⁻¹ChemAxon
Polarizability83.63 ųChemAxon
Number of Rings7ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available