Showing metabocard for 10-Deacetyl-2-debenzoylbaccatin III (LMDB00822)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-30 18:57:15 UTC
Update Date2016-08-01 19:17:41 UTC
LmdbLMDB00822
Secondary Accession NumbersNone
Metabolite Identification
Common Name10-Deacetyl-2-debenzoylbaccatin III
Description10-deacetyl-2-debenzoylbaccatin III belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system. 10-deacetyl-2-debenzoylbaccatin III is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC22H32O9
Average Molecular Weight440.489
Monoisotopic Molecular Weight440.20463261
IUPAC Name(1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,9,12,15-pentahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-4-yl acetate
Traditional Name(1S,2S,3R,4S,7R,9S,10S,12R,15S)-1,2,9,12,15-pentahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-4-yl acetate
CAS Registry NumberNot Available
SMILES
[H][C@@]12C[C@]([H])(O)[C@@]3(C)C(=O)[C@]([H])(O)C4=C(C)[C@@]([H])(O)C[C@@](O)([C@@]([H])(O)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C
InChI Identifier
InChI=1S/C22H32O9/c1-9-11(24)7-22(29)18(28)16-20(5,17(27)15(26)14(9)19(22,3)4)12(25)6-13-21(16,8-30-13)31-10(2)23/h11-13,15-16,18,24-26,28-29H,6-8H2,1-5H3/t11-,12-,13+,15+,16-,18-,20+,21-,22+/m0/s1
InChI KeyLHXBWTCSJBQSGI-QOBCYHTASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTaxanes and derivatives
Alternative Parents
Substituents
  • Taxane diterpenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Oxetane
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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-0.24ALOGPS
logP-1.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.75ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.38 m³·mol⁻¹ChemAxon
Polarizability43.66 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0002900000-3e2321f05092917278ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-0004900000-62fb28bd6793f27d08b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06si-0339200000-f9353b267df037b55402Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1003900000-f38ef7ad463b87cde60aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-6109600000-8646c7e1d62746af4310Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9803000000-9e45730305b8671df756Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID32897
PubChem Compound ID443489
Kegg Compound IDC11899
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available