Nocodazole (CHEM017329)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:14:50 UTC
Update Date2016-11-09 01:15:34 UTC
Accession NumberCHEM017329
Identification
Common NameNocodazole
ClassSmall Molecule
DescriptionA member of the class of benzimidazoles that is benzimidalole which is substituted at position 2 by a (methoxycarbonyl)amino group and at position 5 by a 2-thienoyl group. It is an antineoplastic agent that exerts its effect by depolymerising microtubules.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl)-carbamic acid methyl esterChEBI
Methyl (5-(2-thienylcarbonyl))-1H-benzimidazole-2-ylcarbamateChEBI
Methyl N-(5-thenoyl-2-benzimidazolyl)carbamateChEBI
N-(5-(2-Thenoyl)-2-benzimidazolyl)carbamic acid methyl esterChEBI
N-(5-(2-Thienoyl)-2-benzimidazolyl)carbamic acid methyl esterChEBI
NocodazolChEBI
NocodazolumChEBI
OncodazoleChEBI
R 17934ChEBI
R-17934ChEBI
R17,934ChEBI
(5-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl)-carbamate methyl esterGenerator
Methyl (5-(2-thienylcarbonyl))-1H-benzimidazole-2-ylcarbamic acidGenerator
Methyl N-(5-thenoyl-2-benzimidazolyl)carbamic acidGenerator
N-(5-(2-Thenoyl)-2-benzimidazolyl)carbamate methyl esterGenerator
N-(5-(2-Thienoyl)-2-benzimidazolyl)carbamate methyl esterGenerator
Chemical FormulaC14H11N3O3S
Average Molecular Mass301.320 g/mol
Monoisotopic Mass301.052 g/mol
CAS Registry Number31430-18-9
IUPAC Namemethyl N-[6-(thiophene-2-carbonyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional Namenocodazole
SMILESCOC(=O)NC1=NC2=CC=C(C=C2N1)C(=O)C1=CC=CS1
InChI IdentifierInChI=1S/C14H11N3O3S/c1-20-14(19)17-13-15-9-5-4-8(7-10(9)16-13)12(18)11-3-2-6-21-11/h2-7H,1H3,(H2,15,16,17,19)
InChI KeyKYRVNWMVYQXFEU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Thiophene carboxylic acid or derivatives
  • Aryl ketone
  • Benzenoid
  • Azole
  • Imidazole
  • Thiophene
  • Heteroaromatic compound
  • Ketone
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Carboximidic acid derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility0.018 g/LALOGPS
logP2.84ALOGPS
logP3.17ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.34ChemAxon
pKa (Strongest Basic)3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.39 m³·mol⁻¹ChemAxon
Polarizability30.93 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1790000000-825534d5d7b658640d20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-3790000000-449c2492c2ab67a70502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-32c61dc92bf665194cfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0190000000-0b03ee19763aafda8637Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1490000000-b138a6f40b2cc9f1c17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ldi-4095000000-1acc188f83672b11d1c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-4092000000-a97f7670cc206c37f57cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-c16486ccbe15cf396319Spectrum
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 IDDB08313
HMDB IDHMDB0255688
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNocodazole
Chemspider ID3979
ChEBI ID34892
PubChem Compound ID4122
Kegg Compound IDC13719
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11679255
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20399776
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22002881
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23869451
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=518692
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6384770
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7199049
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7284368
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7344613