Homogentisic Acid
PubChem CID: 780
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| Compound Synonyms | Homogentisic acid, 451-13-8, 2,5-Dihydroxyphenylacetic acid, Alcapton, Homogentisate acid, 2-(2,5-dihydroxyphenyl)acetic acid, Homogentisinic acid, homogentisate, (2,5-Dihydroxyphenyl)acetic acid, Benzeneacetic acid, 2,5-dihydroxy-, 2,5-Dihydroxybenzeneacetic acid, 2,5-Dihydroxy-alpha-toluic acid, Melanic acid, Homogentisinate, Acetic acid, (2,5-dihydroxyphenyl)-, BRN 2692860, 2,5-Dihydroxyphenylacetate, 2,5-Dihydroxy-.alpha.-toluic acid, 2-(3,6-DIHYDROXYPHENYL)ACETIC ACID, EINECS 207-192-7, NP8UE6VF08, NSC 88940, 2,5-DHPOP, 2,5-dihydroxy-benzeneacetic acid, MFCD00004324, NSC-88940, 2,5-Dihydroxy-a-toluate, 2,5-Dihydroxy-alpha-toluate, 2,5-Dihydroxy-benzeneacetate, 2,5-Dihydroxy-a-toluic acid, HOMOGENTISIC ACID [MI], (2,5-dihydroxyphenyl)-Acetate, DTXSID1060005, CHEBI:44747, (2,5-dihydroxyphenyl)-Acetic acid, 4-10-00-01506 (Beilstein Handbook Reference), 71694-00-3, Acid, Homogentisic, UNII-NP8UE6VF08, 1ajp, 4aq6, bmse000200, 2,5Dihydroxyalphatoluic acid, Homogentisic acid (Standard), 2,5Dihydroxyphenylacetic acid, Homogentisic acid, crystalline, SCHEMBL155333, 2,5Dihydroxybenzeneacetic acid, Benzeneacetic acid,5-dihydroxy-, DTXCID6040375, (2,5Dihydroxyphenyl)acetic acid, Acetic acid,5-dihydroxyphenyl)-, Benzeneacetic acid, 2,5dihydroxy, 2-(2,5-dihydroxyphenyl)aceticacid, Acetic acid, (2,5dihydroxyphenyl), NSC88940, RYB46848, s9352, Homogentisic acid, analytical standard, AKOS004910342, DB08327, FH23844, HY-113283R, 1ST40047, AS-19326, SY051598, DB-020087, HY-113283, CS-0059508, D1050, NS00015132, C00544, T70932, Q416054, 5A20D3D5-DF92-400D-AB62-07CC3E7DBFBB, 2,5-Dihydroxybenzeneacetic acid, 2,5-Dihydroxyphenylacetic acid, HQ9 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 77.8 |
| Hydrogen Bond Donor Count | 3.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | C1CCCCC1 |
| Np Classifier Class | Simple phenolic acids |
| Deep Smiles | OC=O)CcccO)ccc6O |
| Heavy Atom Count | 12.0 |
| Classyfire Class | Benzene and substituted derivatives |
| Description | 2-(3,6-dihydroxyphenyl)acetic acid, also known as homogentisic acid or homogentisate, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. 2-(3,6-dihydroxyphenyl)acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-(3,6-dihydroxyphenyl)acetic acid can be found in a number of food items such as gooseberry, angelica, chinese broccoli, and cucumber, which makes 2-(3,6-dihydroxyphenyl)acetic acid a potential biomarker for the consumption of these food products. 2-(3,6-dihydroxyphenyl)acetic acid can be found primarily in blood, feces, and urine, as well as in human cartilage, connective tissue and kidney tissues. In humans, 2-(3,6-dihydroxyphenyl)acetic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 2-(3,6-dihydroxyphenyl)acetic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, tyrosinemia type 3 (TYRO3), alkaptonuria, and tyrosinemia type 2 (or richner-hanhart syndrome). Moreover, 2-(3,6-dihydroxyphenyl)acetic acid is found to be associated with alkaptonuria. 2-(3,6-dihydroxyphenyl)acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Apart from treatment of the complications (such as pain relief using NSAIDs and joint replacement for the cartilage damage), vitamin C has been used to reduce the ochronosis and lowering of the homogentisic acid levels may be attempted with a low-protein diet. Recently the drug nitisinone has been found to suppress homogentisic acid production. Nitrisinone inhibits the enzyme, 4-hydroxyphenylpyruvate dioxygenase, responsible for converting tyrosine to homogentisic acid, thereby blocking the production and accumulation of homogentisic acid. Nitisinone treatment has been shown to cause a 95% reduction in plasma and urinary homogentisic acid (T3DB). |
| Scaffold Graph Node Level | C1CCCCC1 |
| Classyfire Subclass | Phenylacetic acids |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 168.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | P32754, Q93099 |
| Iupac Name | 2-(2,5-dihydroxyphenyl)acetic acid |
| Prediction Hob | 1.0 |
| Class | Benzene and substituted derivatives |
| Veber Rule | True |
| Classyfire Superclass | Benzenoids |
| Xlogp | 0.5 |
| Superclass | Benzenoids |
| Subclass | Phenylacetic acids |
| Gsk 4 400 Rule | True |
| Molecular Formula | C8H8O4 |
| Scaffold Graph Node Bond Level | c1ccccc1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | IGMNYECMUMZDDF-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.125 |
| Logs | 0.41 |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Logd | 0.726 |
| Synonyms | 2,5-Dihydroxyphenylacetic acid, 2-(3,6-DIHYDROXYPHENYL)acetIC ACID, 2,5-Dihydroxyphenylacetate, 2-(3,6-DIHYDROXYPHENYL)acetate, Homogentisate, (2,5-Dihydroxyphenyl)-acetate, (2,5-Dihydroxyphenyl)-acetic acid, 2,5-Dihydroxy-a-toluate, 2,5-Dihydroxy-a-toluic acid, 2,5-Dihydroxy-alpha-toluate, 2,5-Dihydroxy-alpha-toluic acid, 2,5-Dihydroxy-benzeneacetate, 2,5-Dihydroxy-benzeneacetic acid, Alcapton, Homogentisate acid, Homogentisinate, Homogentisinic acid, Melanic acid, Acid, homogentisic, 2,5-dihydroxyphenylacetic acid, homogentisic acid |
| Esol Class | Very soluble |
| Functional Groups | CC(=O)O, cO |
| Compound Name | Homogentisic Acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 168.042 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 168.042 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 168.15 |
| 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 |
| Esol | -1.6623176000000002 |
| Inchi | InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) |
| Smiles | C1=CC(=C(C=C1O)CC(=O)O)O |
| Nring | 1.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | 2(hydroxyphenyl)acetic acids |
| Np Classifier Superclass | Phenolic acids (C6-C1) |
- 1. Outgoing r'ship
FOUND_INto/from Arbutus Unedo (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/10552766 - 2. Outgoing r'ship
FOUND_INto/from Entada Rheedii (Plant) Rel Props:Reference:ISBN:9788185042145 - 3. Outgoing r'ship
FOUND_INto/from Petasites Japonicus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Pinellia Ternata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Sophora Flavescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all