Epothilone B (CHEM019311)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:00:28 UTC
Update Date2026-04-03 15:02:14 UTC
Accession NumberCHEM019311
Identification
Common NameEpothilone B
ClassSmall Molecule
DescriptionEpothilone B is a 16-membered macrolide that mimics the biological effects of taxol.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-Epothilone bChEBI
EPO 906ChEBI
Epo bChEBI
EpoBChEBI
PatupilonaChEBI
PatupilonumChEBI
Epothilon bMeSH
PatupiloneChEBI
Chemical FormulaC27H41NO6S
Average Molecular Mass507.683 g/mol
Monoisotopic Mass507.265 g/mol
CAS Registry Number152044-54-7
IUPAC Name(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Traditional Nameepothilone B
SMILES[H]\C(=C(\C)[C@]1([H])C[C@]2([H])O[C@]2(C)CCC[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C(=O)C(C)(C)[C@@]([H])(O)CC(=O)O1)C1=CSC(C)=N1
InChI IdentifierInChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
InChI KeyQXRSDHAAWVKZLJ-PVYNADRNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassEpothilones and analogues
Direct ParentEpothilones and analogues
Alternative Parents
Substituents
  • Epothilone
  • 2,4-disubstituted 1,3-thiazole
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP3.7ALOGPS
logP4.12ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)2.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity134.76 m³·mol⁻¹ChemAxon
Polarizability56.11 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0000920000-beab03151a77adb7a2a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2310900000-e20b37b4de444c043d28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-2910000000-79555575e98fbdf2aaefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-8210970000-40ae626108a4f2df033dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-4240910000-4edb6aa04ae9117900dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-20fab527e2b8f2f57800Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03010
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00044747
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID31550
PubChem Compound ID448013
Kegg Compound IDC12154
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10831849
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21743064
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22234539
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22688083
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22918719
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23205945
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23214997
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23801302
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24374386
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24470546
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24583341
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24913659
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25694444
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25721485
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25765066
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25919223
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=26081685
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26308485
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26316786