Hippuric Acid
PubChem CID: 464
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| Compound Synonyms | Hippuric acid, 495-69-2, 2-Benzamidoacetic acid, N-Benzoylglycine, Benzoylglycine, Glycine, N-benzoyl-, Benzamidoacetic acid, Benzoylaminoacetic acid, hippurate, Hippursaeure, Phenylcarbonylaminoacetic acid, Benzamidoessigsaeure, Benzoylaminoessigsaeure, N-Benzoyl-glycin, (benzoylamino)acetic acid, Acetic acid, (benzoylamino)-, Acido ippurico, 2-(Phenylformamido)Acetic Acid, Bz-Gly-OH, 66407-11-2, Acido ippurico [Italian], NSC 9982, MFCD00002692, EINECS 207-806-3, UNII-TE0865N2ET, BRN 1073987, TE0865N2ET, DTXSID9046073, CHEBI:18089, AI3-01062, HIPPURICUM ACIDUM, NSC-9982, N-(phenylcarbonyl)glycine, CHEMBL461, DTXCID7026073, 4-09-00-00778 (Beilstein Handbook Reference), NCGC00159486-02, 2-benzamidoacetate, Benzoylaminoethanoic acid, ACETIC ACID,BENZAMIDE HIPPURIC ACID, N-BENZOYL(D5) GLYCINE, CAS-495-69-2, 2-benzamidoaceticacid, Benzoylglycin, benzoyl glycine, hippuric-acid, Benzamidoacetate, Benzoylglycocoll, METHYLAMINOLEVULINATE HYDROCHLORIDE IMPURITY H (EP IMPURITY), METHYLAMINOLEVULINATE HYDROCHLORIDE IMPURITY H [EP IMPURITY], n-benzoyl-glycine, N-benzoyl glycine, Hippuric acid, Na, Hippuric Acid,(S), (benzoylamino)-Acetate, Hippuric acid, 98%, benzoylamino-acetic acid, 2-benzamidoethanoic acid, Phenylcarbonylaminoacetate, Hippuric acid (Standard), (benzoylamino)-Acetic acid, bmse000408, Cambridge id 5116993, HIPPURIC ACID [MI], SCHEMBL7486, TimTec1_002805, Oprea1_124422, Oprea1_492747, MLS001074359, BIDD:ER0490, HIPPURICUM ACIDUM [HPUS], acetic acid, 2-(benzoylamino)-, NSC9982, Hippuric acid, puriss., 99.0%, HMS1541P11, HMS2230I23, HMS3373I07, ALBB-005966, BCP25964, HY-W016562R, Benzenecarboxamide, N-carboxymethyl-, Tox21_111710, BBL008217, BDBM50009999, s5618, STK011394, AKOS000118897, Tox21_111710_1, BS-3968, CCG-266415, CS-W017278, FH23833, HY-W016562, SDCCGMLS-0064636.P001, s11321, NCGC00159486-03, NCGC00159486-04, NCGC00159486-06, SMR000112115, DB-051645, H0143, NS00013745, EN300-16768, C01586, SBI-0633529.0002, AB00375781-06, Q412803, BRD-K62914667-001-13-9, F2111-0036, 2-Benzamidoacetic acid, N-Benzoylglycine, Glycine, N-benzoyl-, 37C5E4E2-F7A0-451C-A041-5C9A71D92FA7, N-Benzoylglycine, 2-(Benzoylamino)acetic acid, 2-Benzamidoacetic acid, 207-806-3, InChI=1/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 66.4 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | C1CCCCC1 |
| Np Classifier Class | Aminoacids |
| Deep Smiles | O=Ccccccc6))))))NCC=O)O |
| Heavy Atom Count | 13.0 |
| Classyfire Class | Benzene and substituted derivatives |
| Description | Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine., Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air., Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460). |
| Scaffold Graph Node Level | C1CCCCC1 |
| Classyfire Subclass | Benzoic acids and derivatives |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 197.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q6IB77, Q969I3, Q8WU03, Q5SZD4, P07943, Q8VC69, Q80UJ1, Q969S8, P02545, Q13951, Q4U2R8, O35956, P84022, Q9R1U7, Q8TCC7, n.a., P0DTD1, P00374 |
| Iupac Name | 2-benzamidoacetic acid |
| Class | Benzene and substituted derivatives |
| Veber Rule | True |
| Classyfire Superclass | Benzenoids |
| Xlogp | 0.3 |
| Superclass | Benzenoids |
| Subclass | Benzoic acids and derivatives |
| Gsk 4 400 Rule | True |
| Molecular Formula | C9H9NO3 |
| Scaffold Graph Node Bond Level | c1ccccc1 |
| Inchi Key | QIAFMBKCNZACKA-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 3.0 |
| State | Solid |
| Synonyms | (benzoylamino)-acetate, (benzoylamino)-acetic acid, (benzoylamino)acetic acid, 2-benzamido-acetic acid, 2-Benzamidoacetate, 2-Benzamidoacetic acid, 532-93-4 (mono-ammonium salt), 532-94-5 (mono-hydrochloride salt), 583-10-8 (mono-potassium salt), Acetic acid, (benzoylamino)-, Acetic acid,benzamide hippuric acid, Acido ippurico, Benzamidoacetate, Benzamidoacetic acid, Benzaminoacetic acid, Benzenecarboxamide, n-carboxymethyl-, Benzoylaminoacetic acid, Benzoylglycin, Benzoylglycine, Benzoylglycocoll, Glycine, n-benzoyl-, Hippurate, Hippuricum acidum, N-(phenylcarbonyl)glycine, N-benzoyl-glycin, N-benzoylglycine, Phenylcarbonylaminoacetate, Phenylcarbonylaminoacetic acid, Benzamidoessigsaeure, Benzoylaminoessigsaeure, Hippursaeure, N-Benzoylglycine, Benzoylaminoacetate, Hippate, Hippic acid, (Benzoylamino)-acetate, (Benzoylamino)-acetic acid, N-Benzoylglycinate, Hippuric acid, hippuric acid |
| Esol Class | Very soluble |
| Functional Groups | CC(=O)O, cC(=O)NC |
| Compound Name | Hippuric Acid |
| Kingdom | Organic compounds |
| Exact Mass | 179.058 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 179.058 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 179.17 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Lipinski Rule Of 5 | True |
| Inchi | 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) |
| Smiles | C1=CC=C(C=C1)C(=O)NCC(=O)O |
| Np Classifier Biosynthetic Pathway | Amino acids and Peptides |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Hippuric acids |
| Np Classifier Superclass | Small peptides |
- 1. Outgoing r'ship
FOUND_INto/from Persea Americana (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Plantago Asiatica (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/19998322 - 3. Outgoing r'ship
FOUND_INto/from Vaccinium Macrocarpon (Plant) Rel Props:Source_db:fooddb_chem_all