ContaminantDB: Ixabepilone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:28:46 UTC

Update Date

2016-11-09 01:17:28 UTC

Accession Number

CHEM022338

Identification

Common Name

Ixabepilone

Class

Small Molecule

Description

Ixabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. On October 16, 2007, the U.S. Food and Drug Administration approved ixabepilone for the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies. Ixabepilone is administered through injection, and will be marketed under the trade name Ixempra. [Wikipedia] Ixabepilone is a semisynthetic analogue of epothilone B. It has a lactone lactam modification that

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aza-epothilone b	HMDB
Azaepothilone b	HMDB
BMS-247550	HMDB
Ixabepilone	MeSH

Chemical Formula

C₂₇H₄₂N₂O₅S

Average Molecular Mass

506.698 g/mol

Monoisotopic Mass

506.281 g/mol

CAS Registry Number

219989-84-1

IUPAC Name

(1S,3S,7R,10S,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]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione

Traditional Name

ixempra

SMILES

C[C@H]1CCC[C@@]2(C)O[C@@]2([H])C[C@H](NC(=O)C[C@@H](O)C(C)(C)C(=O)[C@@H](C)[C@H]1O)C(\C)=C\C1=CSC(C)=N1

InChI Identifier

InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17-,20-,21+,22-,24-,27+/m0/s1

InChI Key

FABUFPQFXZVHFB-CFWQTKTJSA-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Epothilones and analogues

Direct Parent

Epothilones and analogues

Alternative Parents

Substituents

Epothilone
Macrolactam
2,4-disubstituted 1,3-thiazole
Azole
Heteroaromatic compound
Thiazole
Carboxamide group
Ketone
Lactam
Secondary alcohol
Cyclic ketone
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	3.28	ALOGPS
logP	3.39	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.71 m³·mol⁻¹	ChemAxon
Polarizability	57.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ko-1206900000-7e5a87d7a7bb2dfe2473	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-000i-9000034000-b5f94f22d5b0cc02b144	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0000920000-895b7a871811c222d334	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0000900000-3c13cea8febf0aa40a14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-1921200000-0bc925065c5cc4976294	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0abi-8000790000-5b776781d0783345dabd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-5001920000-95a90cd142d884c2d15c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9c67923639010f5c6cc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0000980000-9c850701f82620366891	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000920000-dfe275c993b1d6aac55a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9601200000-375a5afa97b47cce3937	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000090000-b87a3b8bf6933a185f2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0100690000-3f6c0a4495a7db495064	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-732302f674b258c7bbb9	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0015593

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Ixabepilone

Chemspider ID

4949236

ChEBI ID

Not Available

PubChem Compound ID

23305354

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Ixabepilone (CHEM022338)

Structure for CHEM022338: Ixabepilone