ContaminantDB: Nimustine

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:02:57 UTC

Update Date

2016-11-09 01:15:45 UTC

Accession Number

CHEM018182

Identification

Common Name

Nimustine

Class

Small Molecule

Description

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. An antineoplastic agent especially effective against malignant brain tumors.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(4-Amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosourea	ChEBI
3-(4-Amino-2-methyl-5-pyrimidinyl)methyl-1-(2-chloroethyl)-1-nitrosourea	ChEBI
Nimustina	ChEBI
Nimustinum	ChEBI
ACNU	MeSH

Chemical Formula

C₉H₁₃ClN₆O₂

Average Molecular Mass

272.690 g/mol

Monoisotopic Mass

272.079 g/mol

CAS Registry Number

42471-28-3

IUPAC Name

2-chloro-N-{[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]-C-hydroxycarbonimidoyl}-N-nitrosoethan-1-amine

Traditional Name

2-chloro-N-{[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl]-C-hydroxycarbonimidoyl}-N-nitrosoethanamine

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 Key

VFEDRRNHLBGPNN-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.).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Hydropyrimidines

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic cation (CHEBI:75271 )

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	0.093 g/L	ALOGPS
logP	0.63	ALOGPS
logP	0.21	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.85 m³·mol⁻¹	ChemAxon
Polarizability	26.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-074i-9730000000-dd2830cfdc622f7cf9f2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-2940000000-c836eaf58a10745a405c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0609-2900000000-572c9f091ef2282d744d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ka-9500000000-a89bfd7ccfa81fb9da7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0c00-2950000000-c5ea4b8db3b2e5dd4139	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uxr-5950000000-494c4be9ad3e158ef5fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-d4fe58c14da6e796c36d	Spectrum