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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014929

Secondary Accession Numbers

HMDB14929

Metabolite Identification

Common Name

Uracil mustard

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. [PubChem]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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

791
  Mrv0541 02231215002D          

 15 15  0  0  0  0            999 V2000
    1.6500   -0.3630    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.1120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.6005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  2  0  0  0  0
  4 15  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014929

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCN(CCCl)C1=CNC(=O)NC1=O

> <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>
IDPUKCWIGUEADI-UHFFFAOYSA-N

> <FORMULA>
C8H11Cl2N3O2

> <MOLECULAR_WEIGHT>
252.098

> <EXACT_MASS>
251.022832025

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.91267136191089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
0.40531176

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.446032947684088

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.048360675058582

> <JCHEM_PKA_STRONGEST_BASIC>
1.6091536587486126

> <JCHEM_POLAR_SURFACE_AREA>
61.440000000000005

> <JCHEM_REFRACTIVITY>
58.350100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
uracil mustard

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 791                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.678   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       5.748   3.942   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       7.081  -2.988   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.416  -2.988   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   0.092   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748  -2.988   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.082  -0.678   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.748  -0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   2.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -2.218   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   0.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -2.218   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   15                                                            
CONECT    5    8    9   10                                                  
CONECT    6   13   15                                                       
CONECT    7   14   15                                                       
CONECT    8    5   11                                                       
CONECT    9    5   12                                                       
CONECT   10    5   13   14                                                  
CONECT   11    1    8                                                       
CONECT   12    2    9                                                       
CONECT   13    3    6   10                                                  
CONECT   14    7   10                                                       
CONECT   15    4    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(Di-2-chloroethyl)aminouracil	ChEBI
5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione	ChEBI
5-[Di(beta-chloroethyl)amino]uracil	ChEBI
5-Aminouracil mustard	ChEBI
5-N,N-Bis(2-chloroethyl)aminouracil	ChEBI
Aminouracil mustard	ChEBI
Uracil nitrogen mustard	ChEBI
Uramustine	Kegg
5-[Di(b-chloroethyl)amino]uracil	Generator
5-[Di(β-chloroethyl)amino]uracil	Generator
Mustard, uracil	HMDB
5-(Bis(2-chloroethyl)amino)-2,4-(1H,3H)pyrimidinedione	HMDB
Uracil mustard	ChEBI

Chemical Formula

C₈H₁₁Cl₂N₃O₂

Average Molecular Weight

252.098

Monoisotopic Molecular Weight

251.022832025

IUPAC Name

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

Traditional Name

uracil mustard

CAS Registry Number

66-75-1

SMILES

ClCCN(CCCl)C1=CNC(=O)NC1=O

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014929)
Membrane (HMDB: HMDB0014929)

Source

Exogenous

Exogenous (HMDB: HMDB0014929)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.32 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.146	30932474
DeepCCS	[M-H]-	143.314	30932474
DeepCCS	[M-2H]-	180.778	30932474
DeepCCS	[M+Na]+	156.443	30932474
AllCCS	[M+H]+	149.6	32859911
AllCCS	[M+H-H2O]+	146.1	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	153.9	32859911
AllCCS	[M-H]-	148.7	32859911
AllCCS	[M+Na-2H]-	149.3	32859911
AllCCS	[M+HCOO]-	150.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.35 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0633 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1166.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	122.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	360.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	436.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	798.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	367.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1132.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	218.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	18.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Uracil mustard	ClCCN(CCCl)C1=CNC(=O)NC1=O	2735.1	Standard polar	33892256
Uracil mustard	ClCCN(CCCl)C1=CNC(=O)NC1=O	2182.9	Standard non polar	33892256
Uracil mustard	ClCCN(CCCl)C1=CNC(=O)NC1=O	2428.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Uracil mustard,1TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	2197.3	Semi standard non polar	33892256
Uracil mustard,1TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	2319.7	Standard non polar	33892256
Uracil mustard,1TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	3072.2	Standard polar	33892256
Uracil mustard,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	2187.4	Semi standard non polar	33892256
Uracil mustard,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	2279.3	Standard non polar	33892256
Uracil mustard,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	3026.2	Standard polar	33892256
Uracil mustard,2TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O	2262.3	Semi standard non polar	33892256
Uracil mustard,2TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O	2376.8	Standard non polar	33892256
Uracil mustard,2TMS,isomer #1	C[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C)C1=O	2713.9	Standard polar	33892256
Uracil mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	2475.2	Semi standard non polar	33892256
Uracil mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	2553.8	Standard non polar	33892256
Uracil mustard,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)[NH]C1=O	3061.6	Standard polar	33892256
Uracil mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	2423.0	Semi standard non polar	33892256
Uracil mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	2514.6	Standard non polar	33892256
Uracil mustard,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(N(CCCl)CCCl)C1=O	2999.9	Standard polar	33892256
Uracil mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2717.6	Semi standard non polar	33892256
Uracil mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2811.5	Standard non polar	33892256
Uracil mustard,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(N(CCCl)CCCl)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2783.8	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00791	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00791	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00791

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5959

KEGG Compound ID

C11686

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Uramustine

METLIN ID

Not Available

PubChem Compound

6194

PDB ID

Not Available

ChEBI ID

9884

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Uracil mustard (HMDB0014929)

MOL for HMDB0014929 (Uracil mustard)

3D MOL for HMDB0014929 (Uracil mustard)

3D SDF for HMDB0014929 (Uracil mustard)

3D-SDF for HMDB0014929 (Uracil mustard)

PDB for HMDB0014929 (Uracil mustard)

3D PDB for HMDB0014929 (Uracil mustard)

SMILES for HMDB0014929 (Uracil mustard)

INCHI for HMDB0014929 (Uracil mustard)

Structure for HMDB0014929 (Uracil mustard)

3D Structure for HMDB0014929 (Uracil mustard)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized