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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:23:39 UTC
Update Date2021-09-26 23:10:36 UTC
HMDB IDHMDB0255613
Secondary Accession NumbersNone
Metabolite Identification
Common NameNimustine
DescriptionNimustine, also known as nimustinum, belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.). Nimustine is a moderately basic compound (based on its pKa). An 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-amino-2-methylpyrimidin-5-ylmethyl] group. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nimustine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nimustine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1-(4-Amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosoureaChEBI
3-(4-Amino-2-methyl-5-pyrimidinyl)methyl-1-(2-chloroethyl)-1-nitrosoureaChEBI
NimustinaChEBI
NimustinumChEBI
ACNUMeSH
Chemical FormulaC9H13ClN6O2
Average Molecular Weight272.69
Monoisotopic Molecular Weight272.0788514
IUPAC Name2-chloro-N-{[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]-C-hydroxycarbonimidoyl}-N-nitrosoethan-1-amine
Traditional Name2-chloro-N-{[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl]-C-hydroxycarbonimidoyl}-N-nitrosoethanamine
CAS Registry NumberNot Available
SMILES
CC1=NC=C(CN=C(O)N(CCCl)N=O)C(=N)N1
InChI Identifier
InChI=1S/C9H13ClN6O2/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14)
InChI KeyVFEDRRNHLBGPNN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.E. Containing less than the maximum number of double bonds.).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHydropyrimidines
Alternative Parents
Substituents
  • Hydropyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13069
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNimustine
METLIN IDNot Available
PubChem Compound39214
PDB IDNot Available
ChEBI ID75270
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]