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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:59:37 UTC

Update Date

2021-09-26 23:12:10 UTC

HMDB ID

HMDB0256499

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phthalamic acid

Description

2-carbamoylbenzoic acid, also known as phthalamic acid or phthalic acid monoamide, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Based on a literature review a significant number of articles have been published on 2-carbamoylbenzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phthalamic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phthalamic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5    9   10                                                  
CONECT    8    6   11   12                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Aminocarbonyl)benzoic acid	ChEBI
O-Carbamoylbenzoic acid	ChEBI
Phthalamic acid	ChEBI
Phthalamide acid	ChEBI
Phthalamidic acid	ChEBI
Phthalic acid monoamide	ChEBI
Phthalic monoamide	ChEBI
2-(Aminocarbonyl)benzoate	Generator
O-Carbamoylbenzoate	Generator
Phthalamate	Generator
Phthalamidate	Generator
Phthalate monoamide	Generator
2-Carbamoylbenzoate	Generator

Chemical Formula

C₈H₇NO₃

Average Molecular Weight

165.1461

Monoisotopic Molecular Weight

165.042593095

IUPAC Name

2-(C-hydroxycarbonimidoyl)benzoic acid

Traditional Name

2-(C-hydroxycarbonimidoyl)benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=N)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C8H7NO3/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H2,9,10)(H,11,12)

InChI Key

CYMRPDYINXWJFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids

Alternative Parents

Substituents

Benzoic acid
Benzoyl
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamoylbenzoic acid (CHEBI:50736 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.07	ALOGPS
logP	-1.3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	6.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.33 m³·mol⁻¹	ChemAxon
Polarizability	15.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	135.874	30932474
DeepCCS	[M-H]-	132.047	30932474
DeepCCS	[M-2H]-	169.25	30932474
DeepCCS	[M+Na]+	144.789	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phthalamic acid	OC(=N)C1=CC=CC=C1C(O)=O	2862.7	Standard polar	33892256
Phthalamic acid	OC(=N)C1=CC=CC=C1C(O)=O	1608.5	Standard non polar	33892256
Phthalamic acid	OC(=N)C1=CC=CC=C1C(O)=O	1768.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phthalamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C	1742.7	Semi standard non polar	33892256
Phthalamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C	1834.6	Standard non polar	33892256
Phthalamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2005.2	Standard polar	33892256
Phthalamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2407.1	Semi standard non polar	33892256
Phthalamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2392.8	Standard non polar	33892256
Phthalamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2376.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2900000000-ea963029550fedb3c370	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalamic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalamic acid 10V, Positive-QTOF	splash10-0002-0900000000-966b1a9c7ab5c1dc9716	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalamic acid 30V, Positive-QTOF	splash10-0002-0900000000-b6f39e014227ccfd5b65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalamic acid 35V, Positive-QTOF	splash10-0002-0900000000-b2642c84b7617abc8924	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalamic acid 35V, Negative-QTOF	splash10-03di-0900000000-f12d37996ab1f67f45d7	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6691

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

50736

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1290141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Phthalamic acid (HMDB0256499)

MOL for HMDB0256499 (Phthalamic acid)

3D MOL for HMDB0256499 (Phthalamic acid)

3D SDF for HMDB0256499 (Phthalamic acid)

3D-SDF for HMDB0256499 (Phthalamic acid)

PDB for HMDB0256499 (Phthalamic acid)

3D PDB for HMDB0256499 (Phthalamic acid)

SMILES for HMDB0256499 (Phthalamic acid)

INCHI for HMDB0256499 (Phthalamic acid)

Structure for HMDB0256499 (Phthalamic acid)

3D Structure for HMDB0256499 (Phthalamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra