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Identification
NameEpothilone D
Accession NumberDB01873  (EXPT01350)
Typesmall molecule
Groupsexperimental, investigational
DescriptionNot Available
Structure
Thumb
Synonyms
SynonymLanguageCode
KOS-862Not AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number189453-10-9
WeightAverage: 491.683
Monoisotopic: 491.270544117
Chemical FormulaC27H41NO5S
InChI KeyInChIKey=XOZIUKBZLSUILX-UKMAFROXSA-N
InChI
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19-,22+,23+,25+/m0/s1
IUPAC Name
(4R,7S,8R,9S,13Z,16R)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
SMILES
C[C@H]1CCC\C(C)=C/C[C@@H](OC(=O)C[C@@H](O)C(C)(C)C(=O)[C@@H](C)[C@@H]1O)C(\C)=C\C1=CSC(C)=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassMacrolides and Analogues
SubclassEpothilones and Analogues
Direct parentEpothilones and Analogues
Alternative parents2,4-disubstituted Thiazoles; Ketones; Secondary Alcohols; Carboxylic Acid Esters; Polyamines
Substituents2,4-disubstituted 1,3-thiazole; thiazole; azole; secondary alcohol; ketone; carboxylic acid ester; polyamine; carboxylic acid derivative; organonitrogen compound; alcohol; carbonyl group
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationInvestigated for use/treatment in colorectal cancer, lung cancer, breast cancer, solid tumors, and prostate cancer.
PharmacodynamicsNot Available
Mechanism of actionThe principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8749
Blood Brain Barrier + 0.7345
Caco-2 permeable - 0.5948
P-glycoprotein substrate Substrate 0.689
P-glycoprotein inhibitor I Non-inhibitor 0.8151
P-glycoprotein inhibitor II Non-inhibitor 0.9518
Renal organic cation transporter Non-inhibitor 0.9136
CYP450 2C9 substrate Non-substrate 0.8473
CYP450 2D6 substrate Non-substrate 0.8372
CYP450 3A4 substrate Substrate 0.6028
CYP450 1A2 substrate Non-inhibitor 0.5443
CYP450 2C9 substrate Non-inhibitor 0.7697
CYP450 2D6 substrate Non-inhibitor 0.92
CYP450 2C19 substrate Non-inhibitor 0.612
CYP450 3A4 substrate Non-inhibitor 0.835
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8559
Ames test Non AMES toxic 0.6843
Carcinogenicity Non-carcinogens 0.9367
Biodegradation Not ready biodegradable 0.5931
Rat acute toxicity 2.8243 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9905
hERG inhibition (predictor II) Non-inhibitor 0.9322
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.46e-03 g/lALOGPS
logP4.54ALOGPS
logP5.1ChemAxon
logS-5.3ALOGPS
pKa (strongest acidic)14.09ChemAxon
pKa (strongest basic)2.73ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area96.72ChemAxon
rotatable bond count2ChemAxon
refractivity136.04ChemAxon
polarizability55.11ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Ludger Wessjohann, “Epothilone synthesis building blocks III and IV: asymmetrically substituted acyloins and acyloin derivatives, methods for their production and methods for the production of epothilones B, D and epothilone derivatives.” U.S. Patent US20040082651, issued April 29, 2004.

US20040082651
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC12039
PubChem Compound46936246
PubChem Substance46508361
ChemSpider3813699
HETEPD
WikipediaEpothilone
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Tubulin alpha-3C/D chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-3C/D chain Q13748 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Tubulin beta chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin beta chain P07437 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Tubulin beta-1 chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin beta-1 chain Q9H4B7 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Tubulin beta-4B chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin beta-4B chain P68371 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Tubulin beta-4A chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin beta-4A chain P04350 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Tubulin alpha-4A chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-4A chain P68366 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

7. Tubulin beta-3 chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin beta-3 chain Q13509 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Tubulin alpha-1C chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-1C chain Q9BQE3 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Tubulin alpha-8 chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-8 chain Q9NY65 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

10. Tubulin alpha-1B chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-1B chain P68363 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

11. Tubulin alpha-1A chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Tubulin alpha-1A chain Q71U36 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16