T3DB: Uracil mustard

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-09-11 02:06:17 UTC

Update Date

2014-12-24 20:26:56 UTC

Accession Number

T3D4718

Identification

Common Name

Uracil mustard

Class

Small Molecule

Description

Uracil mustard is only found in individuals that have used or taken this drug. It is a nitrogen mustard derivative of uracil. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage. After activation, uracil mustard binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.

Compound Type

Amide
Amine
Drug
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
5-(Di-2-chloroethyl)aminouracil
5-Aminouracil mustard
5-N,N-Bis(2-chloroethyl)aminouracil
5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione
5-[Di(beta-chloroethyl)amino]uracil
Aminouracil mustard
Uracil nitrogen mustard

Chemical Formula

C₈H₁₁Cl₂N₃O₂

Average Molecular Mass

252.098 g/mol

Monoisotopic Mass

251.023 g/mol

CAS Registry Number

66-75-1

IUPAC Name

5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

uracil mustard

SMILES

OC1=NC=C(N(CCCl)CCCl)C(O)=N1

InChI Identifier

InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)

InChI Key

InChIKey=IDPUKCWIGUEADI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Lactam
Tertiary amine
Urea
Organoheterocyclic compound
Azacycle
Alkyl halide
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Organopnictogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nitrogen mustard (CHEBI:9884 )
aminouracil (CHEBI:9884 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	206°C
Boiling Point	Not Available
Solubility	1070 mg/L
LogP	1.2

Predicted Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	0.79	ALOGPS
logP	0.41	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.05	ChemAxon
pKa (Strongest Basic)	1.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.35 m³·mol⁻¹	ChemAxon
Polarizability	22.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0frf-1930000000-b082a72f43cd6ef8d865	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0190000000-ee3938fb1cac655b6750	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0r00-3690000000-e3d7d6c32273a27ea452	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-4900000000-c141e19ee451b1467b29	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0k96-6290000000-93d545f0c9fde44350d4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9220000000-ee1cf7bef8946f7dc9fe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-5577de19673152e348b9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-5f08b1b5a345ae125a3f	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0490000000-86e8889e895d31e6b5a4	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w4i-3900000000-73fd2207850235223106	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9310000000-abaab02ed488d29cc339	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9500000000-fffdc9aec429e5149380	2021-10-11	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0w29-9730000000-047cc283312feb25a4ed	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

After activation, it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (1)

Uses/Sources

Used for its antineoplastic properties.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

9884

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Uracil_mustard

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

1. DNA

General Function:: Used for biological information storage.
Specific Function:: DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:: 2.15 x 10¹² Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Hartley JA, Forrow SM, Souhami RL: Effect of ionic strength and cationic DNA affinity binders on the DNA sequence selective alkylation of guanine N7-positions by nitrogen mustards. Biochemistry. 1990 Mar 27;29(12):2985-91. [2337578 ]

Uracil mustard (T3D4718)

Structure for T3D4718: Uracil mustard

Targets

References