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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:58:37 UTC
Update Date2022-03-07 02:56:13 UTC
HMDB IDHMDB0039495
Secondary Accession Numbers
  • HMDB39495
Metabolite Identification
Common Name2-(Malonylamino)benzoic acid
Description2-(Malonylamino)benzoic acid belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. 2-(Malonylamino)benzoic acid has been detected, but not quantified in, nuts. This could make 2-(malonylamino)benzoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-(Malonylamino)benzoic acid.
Structure
Data?1563863386
Synonyms
ValueSource
2-(Malonylamino)benzoateGenerator
2-[(2-Carboxyacetyl)amino]benzenecarboxylic acidHMDB
2-[(Carboxyacetyl)amino]benzoic acid, 9ciHMDB
N-Malonylanthranilic acidHMDB
N-MalonylanthranilateGenerator
Chemical FormulaC10H9NO5
Average Molecular Weight223.1822
Monoisotopic Molecular Weight223.048072403
IUPAC Name2-(2-carboxyacetamido)benzoic acid
Traditional NameN-malonylanthranilic acid
CAS Registry Number53947-84-5
SMILES
OC(=O)CC(=O)NC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C10H9NO5/c12-8(5-9(13)14)11-7-4-2-1-3-6(7)10(15)16/h1-4H,5H2,(H,11,12)(H,13,14)(H,15,16)
InChI KeyZDSSCYCDBASEJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Substituents
  • Acylaminobenzoic acid or derivatives
  • Benzoic acid
  • Anilide
  • Benzoyl
  • N-arylamide
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Vinylogous amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 - 192 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2853 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP0.26ALOGPS
logP1.41ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-7.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.52 m³·mol⁻¹ChemAxon
Polarizability20.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.36131661259
DarkChem[M-H]-143.58931661259
DeepCCS[M+H]+144.02830932474
DeepCCS[M-H]-141.6730932474
DeepCCS[M-2H]-176.75430932474
DeepCCS[M+Na]+151.35530932474
AllCCS[M+H]+148.032859911
AllCCS[M+H-H2O]+144.232859911
AllCCS[M+NH4]+151.532859911
AllCCS[M+Na]+152.532859911
AllCCS[M-H]-145.732859911
AllCCS[M+Na-2H]-146.032859911
AllCCS[M+HCOO]-146.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-(Malonylamino)benzoic acidOC(=O)CC(=O)NC1=CC=CC=C1C(O)=O3742.3Standard polar33892256
2-(Malonylamino)benzoic acidOC(=O)CC(=O)NC1=CC=CC=C1C(O)=O1967.1Standard non polar33892256
2-(Malonylamino)benzoic acidOC(=O)CC(=O)NC1=CC=CC=C1C(O)=O2166.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-(Malonylamino)benzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)NC1=CC=CC=C1C(=O)O2141.2Semi standard non polar33892256
2-(Malonylamino)benzoic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)CC(=O)O2115.3Semi standard non polar33892256
2-(Malonylamino)benzoic acid,1TMS,isomer #3C[Si](C)(C)N(C(=O)CC(=O)O)C1=CC=CC=C1C(=O)O2080.1Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)NC1=CC=CC=C1C(=O)O[Si](C)(C)C2148.2Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C2075.3Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)CC(=O)O)[Si](C)(C)C2059.3Semi standard non polar33892256
2-(Malonylamino)benzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C2090.2Semi standard non polar33892256
2-(Malonylamino)benzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C2105.6Standard non polar33892256
2-(Malonylamino)benzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)NC1=CC=CC=C1C(=O)O2392.4Semi standard non polar33892256
2-(Malonylamino)benzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)CC(=O)O2372.5Semi standard non polar33892256
2-(Malonylamino)benzoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)CC(=O)O)C1=CC=CC=C1C(=O)O2304.7Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2608.8Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C2536.1Semi standard non polar33892256
2-(Malonylamino)benzoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)CC(=O)O)[Si](C)(C)C(C)(C)C2514.8Semi standard non polar33892256
2-(Malonylamino)benzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2718.7Semi standard non polar33892256
2-(Malonylamino)benzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2607.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Malonylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5920000000-6a0a26330b4c8bcc2ebc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Malonylamino)benzoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9482000000-eda068a249e4625331c72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Malonylamino)benzoic acid 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 - 2-(Malonylamino)benzoic acid 10V, Positive-QTOFsplash10-000i-0960000000-64fc6a5f8ba7bfb3e1dd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 20V, Positive-QTOFsplash10-000i-2910000000-668a44cbbfe2e1449c002016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 40V, Positive-QTOFsplash10-0f76-9600000000-e12348a5340ec3d99efd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 10V, Negative-QTOFsplash10-00b9-1940000000-04d3622576af0a7f7b062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 20V, Negative-QTOFsplash10-003r-2900000000-a94870c3ff32cbae86d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 40V, Negative-QTOFsplash10-0006-9600000000-abe669f5090a3f2199ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 10V, Negative-QTOFsplash10-0006-9400000000-a856f2b65e16f5a0d8df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 20V, Negative-QTOFsplash10-052f-9100000000-7bfc27d77c9c2919404b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 40V, Negative-QTOFsplash10-0006-9300000000-67e8c072fff4814f1d3c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 10V, Positive-QTOFsplash10-00di-0900000000-dfbfe9e3c1ad855f375f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 20V, Positive-QTOFsplash10-00di-0900000000-2a84382389cb76e37ea52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Malonylamino)benzoic acid 40V, Positive-QTOFsplash10-00dl-6900000000-95b9e07d602c6bc2cc892021-09-22Wishart 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 IDFDB019102
KNApSAcK IDC00054078
Chemspider ID388954
KEGG Compound IDC03147
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439922
PDB IDNot Available
ChEBI ID52430
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1877761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .