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Showing metabocard for Dichloromaleimide (HMDB0031151)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:19 UTC
Update Date2023-02-21 17:19:54 UTC
HMDB IDHMDB0031151
Secondary Accession Numbers
  • HMDB31151
Metabolite Identification
Common NameDichloromaleimide
DescriptionDichloromaleimide 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. Based on a literature review a small amount of articles have been published on Dichloromaleimide.
Structure
Data?1676999994
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031151 (Dichloromaleimide)


  Mrv0541 05061305462D          

  9  9  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
M  END
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3D MOL for HMDB0031151 (Dichloromaleimide)

HMDB0031151
     RDKit          3D
Dichloromaleimide
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.3552   -1.5432   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.9058   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -1.4290   -0.1051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4652   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219   -0.5950   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    0.7782   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    2.3761   -0.0739 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.5439   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.7069   -0.0169 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -0.4669    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8  2  1  0
  5 10  1  0
M  END
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3D SDF for HMDB0031151 (Dichloromaleimide)


  Mrv0541 05061305462D          

  9  9  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031151

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(=O)C(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)

> <INCHI_KEY>
KVBAKSQRUXXHCK-UHFFFAOYSA-N

> <FORMULA>
C4HCl2NO2

> <MOLECULAR_WEIGHT>
165.962

> <EXACT_MASS>
164.938433695

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.429126905722796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dichloro-5-hydroxy-2H-pyrrol-2-one

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.5095025126666668

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.223344958862329

> <JCHEM_PKA_STRONGEST_BASIC>
-6.568545671803873

> <JCHEM_POLAR_SURFACE_AREA>
49.660000000000004

> <JCHEM_REFRACTIVITY>
33.2557

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dichloro-5-hydroxypyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0031151 (Dichloromaleimide)

HMDB0031151
     RDKit          3D
Dichloromaleimide
 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.3552   -1.5432   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.9058   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619   -1.4290   -0.1051 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.4652   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219   -0.5950   -0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606    0.7782   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    2.3761   -0.0739 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.5439   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.7069   -0.0169 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -0.4669    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8  2  1  0
  5 10  1  0
M  END
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PDB for HMDB0031151 (Dichloromaleimide)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       3.770   1.651   0.000  0.00  0.00          Cl+0
HETATM    6 Cl   UNK     0       1.060   3.620   0.000  0.00  0.00          Cl+0
HETATM    7  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2    3    5                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    2    7    9                                                  
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    3    4                                                       
CONECT    8    3                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0031151 (Dichloromaleimide)

COMPND    HMDB0031151
HETATM    1  O1  UNL     1      -2.355  -1.543  -0.059  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.248  -0.906  -0.073  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.062  -1.429  -0.105  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.909  -0.465  -0.110  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.322  -0.595  -0.139  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.161   0.778  -0.080  1.00  0.00           C  
HETATM    7 CL1  UNL     1       0.869   2.376  -0.074  1.00  0.00          CL  
HETATM    8  C4  UNL     1      -1.122   0.544  -0.057  1.00  0.00           C  
HETATM    9 CL2  UNL     1      -2.457   1.707  -0.017  1.00  0.00          CL  
HETATM   10  H1  UNL     1       2.860  -0.467   0.714  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   10
CONECT    6    7    8    8
CONECT    8    9
END
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SMILES for HMDB0031151 (Dichloromaleimide)

OC1=NC(=O)C(Cl)=C1Cl
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INCHI for HMDB0031151 (Dichloromaleimide)

InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,4-Dichloro-1H-pyrrole-2,5-dioneHMDB
alpha, beta-DichloromaleimideHMDB
Dichloro-maleimideHMDB
DichloromaleinimideHMDB
Chemical FormulaC4HCl2NO2
Average Molecular Weight165.962
Monoisotopic Molecular Weight164.938433695
IUPAC Name3,4-dichloro-5-hydroxy-2H-pyrrol-2-one
Traditional Name3,4-dichloro-5-hydroxypyrrol-2-one
CAS Registry Number1193-54-0
SMILES
OC1=NC(=O)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C4HCl2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)
InChI KeyKVBAKSQRUXXHCK-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Maleimide
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Pyrroline
  • Vinylogous halide
  • Carboxylic acid derivative
  • Azacycle
  • Vinyl chloride
  • Vinyl halide
  • Chloroalkene
  • Haloalkene
  • Organoheterocyclic compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP0.94ALOGPS
logP0.51ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.26 m³·mol⁻¹ChemAxon
Polarizability12.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+128.59530932474
DeepCCS[M-H]-125.95330932474
DeepCCS[M-2H]-162.60930932474
DeepCCS[M+Na]+137.64730932474
AllCCS[M+H]+132.432859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.632859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-129.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DichloromaleimideOC1=NC(=O)C(Cl)=C1Cl2280.9Standard polar33892256
DichloromaleimideOC1=NC(=O)C(Cl)=C1Cl1560.2Standard non polar33892256
DichloromaleimideOC1=NC(=O)C(Cl)=C1Cl1374.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dichloromaleimide,1TMS,isomer #1C[Si](C)(C)OC1=NC(=O)C(Cl)=C1Cl1504.4Semi standard non polar33892256
Dichloromaleimide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)C(Cl)=C1Cl1752.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dichloromaleimide GC-MS (Non-derivatized) - 70eV, Positivesplash10-044l-5900000000-e975b752f1ab48863c4d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dichloromaleimide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9370000000-64a611a11fba05de59b42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dichloromaleimide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 10V, Positive-QTOFsplash10-014i-0900000000-0f7c59b4c9adaf0085782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 20V, Positive-QTOFsplash10-014i-0900000000-1fb3d6312c50c43770872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 40V, Positive-QTOFsplash10-00kf-9400000000-13aed952f3a2369d56d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 10V, Negative-QTOFsplash10-03di-0900000000-5821571c71986cf12c522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 20V, Negative-QTOFsplash10-03di-0900000000-5821571c71986cf12c522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 40V, Negative-QTOFsplash10-03xr-7900000000-d583e5d3f4b99e2bb6f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 10V, Positive-QTOFsplash10-014i-0900000000-9623ea68367db08a6da72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 20V, Positive-QTOFsplash10-014i-0900000000-9623ea68367db08a6da72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 40V, Positive-QTOFsplash10-052f-9200000000-36d1608933bec6e261df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 10V, Negative-QTOFsplash10-03di-0900000000-ef1da2b7c4781d53f3282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 20V, Negative-QTOFsplash10-03di-0900000000-ef1da2b7c4781d53f3282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dichloromaleimide 40V, Negative-QTOFsplash10-0006-9000000000-7f785f25ab353cffaa622021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003164
KNApSAcK IDNot Available
Chemspider ID13857
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14513
PDB IDNot Available
ChEBI IDNot Available
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. Quintao NL, da Silva GF, Antonialli CS, de Campos-Buzzi F, Correa R, Filho VC: N-antipyrine-3, 4-dichloromaleimide, an effective cyclic imide for the treatment of chronic pain: the role of the glutamatergic system. Anesth Analg. 2010 Mar 1;110(3):942-50. doi: 10.1213/ANE.0b013e3181cbd7f6. [PubMed:20185671 ]
  2. Kazmierczak F: Circular dichroism of some optically active 2,3-dichloromaleimides. Enantiomer. 2001;6(4):251-8. [PubMed:11693488 ]
  3. de Campos F, Correa R, de Souza MM, Yunes RA, Nunes RJ, Cechinel-Filho V: Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative. Arzneimittelforschung. 2002;52(6):455-61. [PubMed:12109046 ]
  4. Lopez SN, Castelli MV, de Campos F, Correa R, Cechinel Filho V, Yunes RA, Zamora MA, Enriz RD, Ribas JC, Furlan RL, Zacchino SA: In vitro antifungal properties structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds. Arzneimittelforschung. 2005;55(2):123-32. [PubMed:15787280 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .