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Record Information
Version2.0
Created at2022-09-05 22:04:03 UTC
Updated at2022-09-05 22:04:03 UTC
NP-MRD IDNP0220685
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3br,4r,5ar,9ar,9br,11as)-1-[(2s)-5-hydroxyhexan-2-yl]-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate
DescriptionAzadiradionol belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1s,3br,4r,5ar,9ar,9br,11as)-1-[(2s)-5-hydroxyhexan-2-yl]-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate is found in Azadirachta indica. Based on a literature review very few articles have been published on Azadiradionol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H44O5
Average Mass484.6770 Da
Monoisotopic Mass484.31887 Da
IUPAC Name(1R,2R,7R,9R,10R,14S,15S)-14-[(2S)-5-hydroxyhexan-2-yl]-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate
Traditional Name(1R,2R,7R,9R,10R,14S,15S)-14-[(2S)-5-hydroxyhexan-2-yl]-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate
CAS Registry NumberNot Available
SMILES
CC(O)CC[C@H](C)[C@@H]1C(=O)C=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)C=CC(=O)C(C)(C)[C@@H]3C[C@@H](OC(C)=O)[C@@]21C
InChI Identifier
InChI=1S/C30H44O5/c1-17(9-10-18(2)31)26-20(33)15-23-29(26,7)13-11-21-28(6)14-12-24(34)27(4,5)22(28)16-25(30(21,23)8)35-19(3)32/h12,14-15,17-18,21-22,25-26,31H,9-11,13,16H2,1-8H3/t17-,18?,21+,22-,25+,26+,28+,29+,30+/m0/s1
InChI KeyCMRZGEHWMGLZNJ-FCJWWUNXSA-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
Azadirachta indicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • 24-hydroxysteroid
  • Monohydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Steroid ester
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 16-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-1-steroid
  • Steroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP5.17ChemAxon
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.14 m³·mol⁻¹ChemAxon
Polarizability56.2 ųChemAxon
Number of Rings4ChemAxon
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 IDC00049626
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102316535
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]