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Record Information
Version2.0
Created at2022-04-27 23:21:42 UTC
Updated at2022-04-27 23:21:42 UTC
NP-MRD IDNP0052223
Secondary Accession NumbersNone
Natural Product Identification
Common NameTaccalonolide A
Description(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁷,⁹.0¹⁶,²⁴.0¹⁹,²³]Pentacos-18-en-10-yl acetate 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. Taccalonolide A is found in Tacca chantrieri and Tacca plantaginea. Based on a literature review very few articles have been published on (1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0²,¹².0⁵,¹¹.0⁷,⁹.0¹⁶,²⁴.0¹⁹,²³]Pentacos-18-en-10-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-Tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0,.0,.0,.0,.0,]pentacos-18-en-10-yl acetic acidGenerator
Chemical FormulaC36H46O14
Average Mass702.7500 Da
Monoisotopic Mass702.28876 Da
IUPAC Name(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0^{2,12}.0^{5,11}.0^{7,9}.0^{16,24}.0^{19,23}]pentacos-18-en-10-yl acetate
Traditional Name(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17R,22S,23S,24R,25S)-13,14,25-tris(acetyloxy)-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.0^{2,12}.0^{5,11}.0^{7,9}.0^{16,24}.0^{19,23}]pentacos-18-en-10-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1C=C2OC(=O)[C@@](C)(O)[C@]2(C)[C@@H]2[C@@H](OC(C)=O)[C@H]3[C@@H]4[C@@H](O)C(=O)[C@H]5C[C@@H]6O[C@@H]6[C@H](OC(C)=O)[C@@]5(C)[C@H]4[C@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)[C@@H]12
InChI Identifier
InChI=1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)11-18-27(49-18)30(33)47-15(4)39/h10,12,17-18,20-24,26-31,42,44H,11H2,1-9H3/t12-,17+,18-,20-,21-,22+,23+,24-,26+,27-,28-,29-,30-,31-,33+,34+,35-,36+/m0/s1
InChI KeyPTTJLTMUKRRHAT-ONNNFQRSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tacca chantrieriLOTUS Database
Tacca plantagineaPlant
Chemical Taxonomy
Description 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
  • Steroid ester
  • 6-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Pentacarboxylic acid or derivatives
  • Oxepane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Enol ester
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • 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
logP2.11ALOGPS
logP0.0088ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)11.99ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area201.56 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity167.08 m³·mol⁻¹ChemAxon
Polarizability70.52 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
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 Compound162862626
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available