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Record Information
Version1.0
Created at2022-09-12 15:11:09 UTC
Updated at2022-09-12 15:11:09 UTC
NP-MRD IDNP0330128
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4r,5r,7s)-7-[(1s,2r,3as,3bs,5ar,6s,9ar,9bs,11as)-1,2,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one
DescriptionAnomanolide F belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (1r,4r,5r,7s)-7-[(1s,2r,3as,3bs,5ar,6s,9ar,9bs,11as)-1,2,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3ah,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one is found in Tubocapsicum anomalum. Based on a literature review very few articles have been published on anomanolide F.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H40O8
Average Mass504.6200 Da
Monoisotopic Mass504.27232 Da
IUPAC Name(1R,4R,5R,7S)-4-hydroxy-4,5-dimethyl-7-[(1S,2R,6S,7R,10S,11S,13R,14S,15S)-6,7,13,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-14-yl]-2-oxabicyclo[3.2.1]octan-3-one
Traditional Name(1R,4R,5R,7S)-4-hydroxy-4,5-dimethyl-7-[(1S,2R,6S,7R,10S,11S,13R,14S,15S)-6,7,13,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-14-yl]-2-oxabicyclo[3.2.1]octan-3-one
CAS Registry NumberNot Available
SMILES
C[C@@]12C[C@@H](OC(=O)[C@]1(C)O)[C@H](C2)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3CC[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C28H40O8/c1-23-12-17(18(13-23)36-22(32)26(23,4)33)28(35)21(31)11-16-14-7-10-27(34)20(30)6-5-19(29)25(27,3)15(14)8-9-24(16,28)2/h5-6,14-18,20-21,30-31,33-35H,7-13H2,1-4H3/t14-,15+,16+,17+,18-,20+,21-,23-,24+,25+,26+,27+,28-/m1/s1
InChI KeyIIXRXLFGAXOZNE-XUQMPVOBSA-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
Tubocapsicum anomalumLOTUS 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
  • 24-hydroxysteroid
  • Prostaglandin skeleton
  • Steroid lactone
  • Eicosanoid
  • Androstane-skeleton
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • Hydroxysteroid
  • 5-hydroxysteroid
  • 4-hydroxysteroid
  • Caprolactone
  • Cyclohexenone
  • Oxepane
  • Delta_valerolactone
  • Delta valerolactone
  • Fatty acyl
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP1.11ChemAxon
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity129.3 m³·mol⁻¹ChemAxon
Polarizability53.89 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
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 IDC00038464
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102086554
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]