Cannabis Compound Database: Showing Compound Card for Hippuric acid (CDB006338)

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Record Information

Version

1.0

Created at

2020-09-11 15:49:36 UTC

Updated at

2022-12-13 23:36:27 UTC

CannabisDB ID

CDB006338

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Hippuric acid

Description

Hippuric acid, also known as N-benzoylglycine or hippurate, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Hippuric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hippuric acid is found, on average, in the highest concentration within milk (cow). Hippuric acid has also been detected, but not quantified in, american cranberries and avocado. This could make hippuric acid a potential biomarker for the consumption of these foods. An N-acylglycine in which the acyl group is specified as benzoyl. Hippuric acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzamidoacetic acid	ChEBI
Benzamidoessigsaeure	ChEBI
Benzoylaminoacetic acid	ChEBI
Benzoylaminoessigsaeure	ChEBI
Hippurate	ChEBI
Hippursaeure	ChEBI
Phenylcarbonylaminoacetic acid	ChEBI
N-Benzoylglycine	Kegg
Benzamidoacetate	Generator
Benzoylaminoacetate	Generator
Phenylcarbonylaminoacetate	Generator
Hippate	Generator
Hippic acid	Generator
(Benzoylamino)-acetate	HMDB
(Benzoylamino)-acetic acid	HMDB
2-Benzamidoacetate	HMDB
2-Benzamidoacetic acid	HMDB
Benzoylglycine	HMDB
N-Benzoylglycinate	HMDB
Hippuric acid	HMDB

Chemical Formula

C₉H₉NO₃

Average Molecular Weight

179.1727

Monoisotopic Molecular Weight

179.058243159

IUPAC Name

2-(phenylformamido)acetic acid

Traditional Name

hippuric acid

CAS Registry Number

Not Available

SMILES

OC(=O)CNC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)

InChI Key

QIAFMBKCNZACKA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Benzoyl
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:18089 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.23	ALOGPS
logP	0.53	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.12 m³·mol⁻¹	ChemAxon
Polarizability	17.57 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5900000000-99084c1783177c807011	2014-09-20	View Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0930000000-6f50aaca6d403e269682	Spectrum
GC-MS	Hippuric acid, 1 TMS, GC-MS Spectrum	splash10-0a4i-5930000000-166d57ae498305a4eee9	Spectrum
GC-MS	Hippuric acid, 2 TMS, GC-MS Spectrum	splash10-0a4i-4920000000-358e012cae8853105371	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a6r-8900000000-01e7057139a995115ddb	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0il0-9700000000-5eb7d5acc34cdb44f3e0	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2910000000-fac0a1c19c9209e1daf5	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0930000000-6f50aaca6d403e269682	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-5930000000-166d57ae498305a4eee9	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-4920000000-358e012cae8853105371	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2910000000-19b240c27664cf096501	Spectrum
GC-MS	Hippuric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0930000000-b1d771fba596fcbf4d44	Spectrum
Predicted GC-MS	Hippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-2900000000-3f2da6ec78f21732afea	Spectrum
Predicted GC-MS	Hippuric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9810000000-58ac2f50544c1db5247f	Spectrum
Predicted GC-MS	Hippuric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hippuric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hippuric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hippuric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0059-1900000000-412e9313d23685caab38	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-9100000000-cc560a494407b3c33abb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-004i-9200000000-103f81d635660cdb0aa0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-8900000000-734176188abc8a1dd766	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a6r-6900000000-9bebc859a11a987fc2d4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-7f332f3c98391a276547	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9200000000-fc8a26847a77460ed21a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a6r-9000000000-9c160b377301023f1df2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-7f332f3c98391a276547	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-003r-2900000000-a8b444dcb0522a2aab6d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9200000000-d20e52137daf3db2f638	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-1beabd6a9820b379f52f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-7ac8420c577cebb0e8a9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0900000000-fae7f8c300bf6943f8d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-003r-0900000000-5d25dcc019489d867073	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-003r-0900000000-ef98916bdf0fc8627083	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0900000000-cbfff04acbf0c95d7e30	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-65954d58bf9851d84f75	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-730b49f058aae1303aba	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9500000000-2707fadcc633cb9d989c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8040a946088ae227b41e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-48c46f688fb318e3a7ba	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-4ded9b0d44ce0068065d	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.00318 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.001052 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.000989 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00121 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00105 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.000482 mg/g dry wt	David S. Wishart,...	details