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Record Information
Version2.0
Created at2022-09-04 20:29:10 UTC
Updated at2022-09-04 20:29:10 UTC
NP-MRD IDNP0201440
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-[(1r,3as,3br,5as,7s,9ar,9bs,10r,11ar)-3a,5a,7,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one
Description11Alpha,19-dihydroxytelocinobufagin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Thus, 11alpha,19-dihydroxytelocinobufagin is considered to be a sterol. 5-[(1r,3as,3br,5as,7s,9ar,9bs,10r,11ar)-3a,5a,7,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one is found in Rhinella marina. Based on a literature review very few articles have been published on 11alpha,19-dihydroxytelocinobufagin.
Structure
Thumb
Synonyms
ValueSource
11a,19-DihydroxytelocinobufaginGenerator
11Α,19-dihydroxytelocinobufaginGenerator
Chemical FormulaC24H34O7
Average Mass434.5290 Da
Monoisotopic Mass434.23045 Da
IUPAC Name5-[(1S,2R,5S,7S,10R,11S,14S,15R,17R)-5,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2H-pyran-2-one
Traditional Name5-[(1S,2R,5S,7S,10R,11S,14S,15R,17R)-5,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pyran-2-one
CAS Registry NumberNot Available
SMILES
C[C@]12C[C@@H](O)[C@H]3[C@@H](CC[C@]4(O)C[C@@H](O)CC[C@]34CO)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1
InChI Identifier
InChI=1S/C24H34O7/c1-21-11-18(27)20-17(5-8-23(29)10-15(26)4-7-22(20,23)13-25)24(21,30)9-6-16(21)14-2-3-19(28)31-12-14/h2-3,12,15-18,20,25-27,29-30H,4-11,13H2,1H3/t15-,16+,17+,18+,20+,21+,22-,23-,24-/m0/s1
InChI KeyWHVSTINJJCCIPI-RNROHMHZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Rhinella marinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBufanolides and derivatives
Alternative Parents
Substituents
  • Bufanolide-skeleton
  • 19-hydroxysteroid
  • 3-hydroxysteroid
  • 14-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 11-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Pyranone
  • Pyran
  • Tertiary alcohol
  • Heteroaromatic compound
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary 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
logP-0.54ChemAxon
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity113.34 m³·mol⁻¹ChemAxon
Polarizability46.48 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 ID8178624
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10003044
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]