Homogentisic acid

Details

• Internal ID: d641b404-d54a-4ee3-b343-510ddf3d4eb7
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylacetic acids > 2(hydroxyphenyl)acetic acids
• IUPAC Name: 2-(2,5-dihydroxyphenyl)acetic acid
• SMILES (Canonical): C1=CC(=C(C=C1O)CC(=O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1O)CC(=O)O)O
• 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)
• InChI Key: IGMNYECMUMZDDF-UHFFFAOYSA-N
• Popularity: 1,712 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15 g/mol
• Exact Mass: 168.04225873 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 451-13-8
• 2,5-Dihydroxyphenylacetic acid
• Alcapton
• Homogentisate acid
• Homogentisinic acid
• 2-(2,5-dihydroxyphenyl)acetic acid
• homogentisate
• (2,5-Dihydroxyphenyl)acetic acid
• Benzeneacetic acid, 2,5-dihydroxy-
• 2,5-Dihydroxybenzeneacetic acid
• 2,5-Dihydroxy-alpha-toluic acid
• Melanic acid
• 2,5-Dihydroxyphenylacetate
• 2,5-DHPOP
• Acetic acid, (2,5-dihydroxyphenyl)-
• BRN 2692860
• 2-(3,6-DIHYDROXYPHENYL)ACETIC ACID
• 2,5-Dihydroxy-.alpha.-toluic acid
• EINECS 207-192-7
• NSC 88940
• UNII-NP8UE6VF08
• NP8UE6VF08
• NSC-88940
• 2,5-dihydroxy-benzeneacetic acid
• 4-10-00-01506 (Beilstein Handbook Reference)
• 71694-00-3
• 2-(2,5-dihydroxyphenyl)acetate
• Homogentisinate
• 1ajp
• 4aq6
• 2,5-Dihydroxy-a-toluate
• bmse000200
• 2,5-Dihydroxy-alpha-toluate
• 2,5-Dihydroxy-benzeneacetate
• 2,5-Dihydroxy-a-toluic acid
• Homogentisic acid, crystalline
• SCHEMBL155333
• HOMOGENTISIC ACID [MI]
• (2,5-dihydroxyphenyl)-Acetate
• Benzeneacetic acid,5-dihydroxy-
• DTXSID1060005
• Acetic acid,5-dihydroxyphenyl)-
• CHEBI:44747
• 2-(2,5-dihydroxyphenyl)aceticacid
• (2,5-dihydroxyphenyl)-Acetic acid
• NSC88940
• MFCD00004324
• s9352
• Homogentisic acid, analytical standard
• AKOS004910342
• DB08327
• AS-19326
• HY-113283
• CS-0059508
• D1050
• FT-0610384
• FT-0669226
• C00544
• T70932
• A826718
• Q416054
• W-109536
• 5A20D3D5-DF92-400D-AB62-07CC3E7DBFBB
• HQ9
• InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9688	96.88%
Caco-2	+	0.5414	54.14%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.9108	91.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9395	93.95%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9708	97.08%
P-glycoprotein inhibitior	-	0.9904	99.04%
P-glycoprotein substrate	-	0.9847	98.47%
CYP3A4 substrate	-	0.7745	77.45%
CYP2C9 substrate	+	0.8019	80.19%
CYP2D6 substrate	-	0.8141	81.41%
CYP3A4 inhibition	-	0.9404	94.04%
CYP2C9 inhibition	-	0.9533	95.33%
CYP2C19 inhibition	-	0.9432	94.32%
CYP2D6 inhibition	-	0.9609	96.09%
CYP1A2 inhibition	-	0.9660	96.60%
CYP2C8 inhibition	-	0.7992	79.92%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7740	77.40%
Carcinogenicity (trinary)	Non-required	0.7190	71.90%
Eye corrosion	-	0.9101	91.01%
Eye irritation	+	0.9963	99.63%
Skin irritation	+	0.7538	75.38%
Skin corrosion	-	0.8901	89.01%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8348	83.48%
Micronuclear	+	0.5795	57.95%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	+	0.7507	75.07%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7245	72.45%
Acute Oral Toxicity (c)	III	0.7573	75.73%
Estrogen receptor binding	-	0.8293	82.93%
Androgen receptor binding	-	0.4857	48.57%
Thyroid receptor binding	-	0.8169	81.69%
Glucocorticoid receptor binding	-	0.5199	51.99%
Aromatase binding	-	0.7888	78.88%
PPAR gamma	-	0.5164	51.64%
Honey bee toxicity	-	0.9719	97.19%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.8882	88.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.44%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.22%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.67%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.81%	96.09%
CHEMBL3194	P02766	Transthyretin	86.31%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.26%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.56%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.11%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.09%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.24%	94.62%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	80.57%	88.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.48%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.03%	90.71%

Plants that contains it

• Arbutus unedo
• Lupinus albus
• Petasites japonicus
• Pinellia ternata

Cross-Links

• PubChem: 780
• NPASS: NPC167345
• LOTUS: LTS0178183
• wikiData: Q416054