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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:19:58 UTC

Update Date

2021-09-26 22:55:18 UTC

HMDB ID

HMDB0246304

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(Dimethylamino)benzoic acid

Description

4-(Dimethylamino)benzoic acid belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Based on a literature review very few articles have been published on 4-(Dimethylamino)benzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(dimethylamino)benzoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(Dimethylamino)benzoic 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: XP1                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -15.405 -40.192   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0     -15.405 -41.732   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0     -14.072 -42.502   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.739 -42.502   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -16.739 -44.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.073 -44.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -19.406 -44.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -20.740 -44.812   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -20.740 -46.352   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0     -19.406 -42.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -18.073 -41.732   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -22.074 -44.042   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11    4   10                                                       
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
4-(Dimethylamino)benzoate	Generator
4-dimethylamino-Benzoic acid	ChEMBL
4-dimethylamino-Benzoate	Generator
P-Dimethylaminobenzoic acid	MeSH
4-(dimethylamino)Benzoic acid, lithium salt	MeSH
4-(dimethylamino)Benzoic acid, sodium salt	MeSH
Para-dimethylaminobenzoic acid	MeSH
4EDMAB	MeSH

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

4-(dimethylamino)benzoic acid

Traditional Name

4-(dimethylamino)benzoic acid

CAS Registry Number

Not Available

SMILES

CN(C)C1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H11NO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6H,1-2H3,(H,11,12)

InChI Key

YDIYEOMDOWUDTJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Amino acid or derivatives
Amino acid
Tertiary amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0246304)

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	1.51	ALOGPS
logP	1.6	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.76	ChemAxon
pKa (Strongest Basic)	2.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.74 m³·mol⁻¹	ChemAxon
Polarizability	17.61 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]+	134.369	30932474
DeepCCS	[M-H]-	130.541	30932474
DeepCCS	[M-2H]-	168.056	30932474
DeepCCS	[M+Na]+	143.594	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	135.3	32859911
AllCCS	[M+Na-2H]-	136.4	32859911
AllCCS	[M+HCOO]-	137.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.2937 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1350.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	331.9 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	362.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	881.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	267.7 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	1087.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	426.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	247.4 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	103.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(Dimethylamino)benzoic acid	CN(C)C1=CC=C(C=C1)C(O)=O	2582.2	Standard polar	33892256
4-(Dimethylamino)benzoic acid	CN(C)C1=CC=C(C=C1)C(O)=O	1708.3	Standard non polar	33892256
4-(Dimethylamino)benzoic acid	CN(C)C1=CC=C(C=C1)C(O)=O	1739.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-(Dimethylamino)benzoic acid EI-B (Non-derivatized)	splash10-02t9-3900000000-2c3d138038a38784bb91	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Dimethylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ba-1900000000-60aadc55ccf7b70ba268	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Dimethylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Dimethylamino)benzoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Dimethylamino)benzoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 10V, Positive-QTOF	splash10-014i-0900000000-5dbccd7986aebff85807	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 20V, Positive-QTOF	splash10-014i-0900000000-a5edd438522ffe083089	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 40V, Positive-QTOF	splash10-0aba-5900000000-2e58937f739f1a6c442e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 10V, Negative-QTOF	splash10-03di-0900000000-b72b16854f0cde642bae	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 20V, Negative-QTOF	splash10-0229-0900000000-21e8e502ae56e8ece21a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 40V, Negative-QTOF	splash10-0uk9-2900000000-503176cd2b30c282adad	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 10V, Positive-QTOF	splash10-014i-0900000000-528cd626a787a972f3b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 20V, Positive-QTOF	splash10-0002-0900000000-e350aad40ac5cf49689d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 40V, Positive-QTOF	splash10-0ir0-3900000000-0fbf917daa0b8d95031b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 10V, Negative-QTOF	splash10-03di-0900000000-60ef8ed6ade6bfe9f473	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 20V, Negative-QTOF	splash10-0fk9-0900000000-5d2470f4a991a19fcf13	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Dimethylamino)benzoic acid 40V, Negative-QTOF	splash10-0uxu-9100000000-94642e4e8f92f8748ca8	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

DB08748

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11595

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

Not Available

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

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 4-(Dimethylamino)benzoic acid (HMDB0246304)

MOL for HMDB0246304 (4-(Dimethylamino)benzoic acid)

3D MOL for HMDB0246304 (4-(Dimethylamino)benzoic acid)

3D SDF for HMDB0246304 (4-(Dimethylamino)benzoic acid)

3D-SDF for HMDB0246304 (4-(Dimethylamino)benzoic acid)

PDB for HMDB0246304 (4-(Dimethylamino)benzoic acid)

3D PDB for HMDB0246304 (4-(Dimethylamino)benzoic acid)

SMILES for HMDB0246304 (4-(Dimethylamino)benzoic acid)

INCHI for HMDB0246304 (4-(Dimethylamino)benzoic acid)

Structure for HMDB0246304 (4-(Dimethylamino)benzoic acid)

3D Structure for HMDB0246304 (4-(Dimethylamino)benzoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra