1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea (Methyl-CCNU) (see Semustine) (CHEM016146)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:16:41 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016146
Identification
Common Name1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosourea (Methyl-CCNU) (see Semustine)
ClassSmall Molecule
DescriptionAn organochlorine compound that is urea in which the two hydrogens on one of the amino groups are replaced by nitroso and 2-chloroethyl groups and one hydrogen from the other amino group is replaced by a 4-methylcyclohexyl group.
Contaminant Sources
  • IARC Carcinogens General
  • IARC Carcinogens Group 1
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(2-Chloroethyl)-1-([(4-methylcyclohexyl)amino]carbonyl)-2-oxohydrazineChEBI
1-(2-Chloroethyl)-3-(4-methylcyclohexyl)-1-nitrosoureaChEBI
Methyl-ccnuChEBI
N-(2-Chloroethyl)-n'-(4-methylcyclohexyl)-N-nitrosoureaChEBI
SemustinaChEBI
SemustinumChEBI
Me ccnuMeSH
Me-ccnuMeSH
MeCCNUMeSH
Methyl ccnuMeSH
Chemical FormulaC10H18ClN3O2
Average Molecular Mass247.720 g/mol
Monoisotopic Mass247.109 g/mol
CAS Registry Number13909-09-6
IUPAC Name3-(2-chloroethyl)-1-(4-methylcyclohexyl)-3-nitrosourea
Traditional Namesemustine
SMILESCC1CCC(CC1)NC(=O)N(CCCl)N=O
InChI IdentifierInChI=1S/C10H18ClN3O2/c1-8-2-4-9(5-3-8)12-10(15)14(13-16)7-6-11/h8-9H,2-7H2,1H3,(H,12,15)
InChI KeyFVLVBPDQNARYJU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentNitrosoureas
Alternative Parents
Substituents
  • Nitrosourea
  • Semicarbazide
  • Nitrosamide
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alkyl chloride
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Organic nitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 Solubility0.38 g/LALOGPS
logP2.9ALOGPS
logP2.44ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.2 m³·mol⁻¹ChemAxon
Polarizability25.68 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0a4m-9620000000-b1ca32de400361b3736eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-4960000000-f1f37a2a874c270e824eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-5900000000-bad49b3a80f4d8707f3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9100000000-d3aea4bab5aa909da42fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06s2-1930000000-07403d68a4f621496316Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3930000000-6e57cc77d4d7615d6730Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9500000000-90633626bba54c296850Spectrum
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 IDNot Available
HMDB IDHMDB0258228
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSemustine
Chemspider ID5009
ChEBI ID6863
PubChem Compound IDNot Available
Kegg Compound IDC07640
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19537027
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19782419
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21698685
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21807073
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22381771
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22385186
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23224642
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2329971
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23570586
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3941685
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6217886
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6353233
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6708984
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6953997
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=7032289
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7083244
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7306917
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=922750