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Record Information
Version2.0
Created at2022-09-06 22:24:38 UTC
Updated at2022-09-06 22:24:38 UTC
NP-MRD IDNP0238927
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,4s,7r,8r,9s,10s,12s,13s,16r)-13-(acetyloxy)-7,8,10,12-tetrahydroxy-5,9-dimethyl-2-(prop-1-en-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-5-en-4-yl acetate
Description(2AS)-5aalpha,8-Dimethyl-2abeta,9beta-diacetoxy-10aalpha-isopropenyl-2a,3,4,5,5a,6,7,9,10,10a,10balpha,10cbeta-dodecahydro-2H-1-oxabenzo[cd]cyclopenta[h]azulene-3beta,5alpha,6beta,7alpha-tetraol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,2s,4s,7r,8r,9s,10s,12s,13s,16r)-13-(acetyloxy)-7,8,10,12-tetrahydroxy-5,9-dimethyl-2-(prop-1-en-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-5-en-4-yl acetate is found in Taxus canadensis. Based on a literature review very few articles have been published on (2aS)-5aalpha,8-Dimethyl-2abeta,9beta-diacetoxy-10aalpha-isopropenyl-2a,3,4,5,5a,6,7,9,10,10a,10balpha,10cbeta-dodecahydro-2H-1-oxabenzo[cd]cyclopenta[h]azulene-3beta,5alpha,6beta,7alpha-tetraol.
Structure
Thumb
Synonyms
ValueSource
(2AS)-5aalpha,8-dimethyl-2abeta,9b-diacetoxy-10aalpha-isopropenyl-2a,3,4,5,5a,6,7,9,10,10a,10balpha,10cbeta-dodecahydro-2H-1-oxabenzo[CD]cyclopenta[H]azulene-3b,5a,6b,7a-tetraolGenerator
(2AS)-5aalpha,8-dimethyl-2abeta,9β-diacetoxy-10aalpha-isopropenyl-2a,3,4,5,5a,6,7,9,10,10a,10balpha,10cbeta-dodecahydro-2H-1-oxabenzo[CD]cyclopenta[H]azulene-3β,5α,6β,7α-tetraolGenerator
Chemical FormulaC24H34O9
Average Mass466.5270 Da
Monoisotopic Mass466.22028 Da
IUPAC Name(1S,2S,4S,7R,8R,9S,10S,12S,13S,16R)-13-(acetyloxy)-7,8,10,12-tetrahydroxy-5,9-dimethyl-2-(prop-1-en-2-yl)-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-5-en-4-yl acetate
Traditional Name(1S,2S,4S,7R,8R,9S,10S,12S,13S,16R)-13-(acetyloxy)-7,8,10,12-tetrahydroxy-5,9-dimethyl-2-(prop-1-en-2-yl)-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-5-en-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@H]1C[C@]2([C@H]3OC[C@@]4(OC(C)=O)[C@@H]3[C@@](C)([C@@H](O)C[C@@H]4O)[C@@H](O)[C@H](O)C2=C1C)C(C)=C
InChI Identifier
InChI=1S/C24H34O9/c1-10(2)23-8-14(32-12(4)25)11(3)17(23)18(29)20(30)22(6)15(27)7-16(28)24(33-13(5)26)9-31-21(23)19(22)24/h14-16,18-21,27-30H,1,7-9H2,2-6H3/t14-,15-,16-,18+,19-,20-,21-,22+,23-,24-/m0/s1
InChI KeyUNPHDVLMOFWPKV-VEDVJMMMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Taxus canadensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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
logP-1.5ChemAxon
pKa (Strongest Acidic)13.14ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.67 m³·mol⁻¹ChemAxon
Polarizability47.86 ųChemAxon
Number of Rings4ChemAxon
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 ID28285434
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102474305
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]