Select a section from the left sidebar
Homogentisic acid
- Family: Plantae - Mimosaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Acid
| Canonical Smiles | OC(=O)Cc1cc(O)ccc1O |
|---|---|
| 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) |
| InChIKey | IGMNYECMUMZDDF-UHFFFAOYSA-N |
| Formula | C8H8O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 168.15 |
| Rotatable Bonds | 2 |
| TPSA | 77.76 |
| LogP | 0.72 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.12 |
| Exact Mass | 168.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Entada rheedei | Leguminosae/Fabaceae | Plantae | 204974 |
| 2 | Entada rheedei | Mimosaceae | Plantae | 204974 |
Showing of synonyms
Homogentisic acid
451-13-8
2,5-Dihydroxyphenylacetic acid
2-(2,5-dihydroxyphenyl)acetic acid
Alcapton
Homogentisate acid
Homogentisinic acid
(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-Dihydroxy-.alpha.-toluic acid
2-(3,6-DIHYDROXYPHENYL)ACETIC ACID
EINECS 207-192-7
NP8UE6VF08
NSC 88940
2,5-dihydroxy-benzeneacetic acid
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)
Acid, Homogentisic
2,5Dihydroxyalphatoluic acid
2,5Dihydroxyphenylacetic acid
2,5Dihydroxybenzeneacetic acid
DTXCID6040375
(2,5Dihydroxyphenyl)acetic acid
Benzeneacetic acid, 2,5dihydroxy
Acetic acid, (2,5dihydroxyphenyl)
Inchi=1/c8h8o4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10h,4h2,(h,11,12
Homogentisate
2,5-Dihydroxyphenylacetate
2,5-DHPOP
MFCD00004324
71694-00-3
UNII-NP8UE6VF08
1ajp
4aq6
Bmse000200
Homogentisic acid (Standard)
Homogentisic acid, crystalline
SCHEMBL155333
Benzeneacetic acid,5-dihydroxy-
Acetic acid,5-dihydroxyphenyl)-
2-(2,5-dihydroxyphenyl)aceticacid
MSK40047
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
HQ9
Pubchem:
780
Cas:
451-13-8
Gnps:
CCMSLIB00006676037
Zinc:
ZINC000000388428
Kegg Ligand:
C00544
Chebi:
44747
Nmrshiftdb2:
20039579
Metabolights:
MTBLC44747
Comptox:
DTXSID1060005
Drugbank:
DB08327
Pdb Ligand:
OMD
CPRiL:
22609
SMILES: c1ccccc1
Level: 0
Mol. Weight: 168.15 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.44
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.98
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.56
- Plasma Protein Binding
- 18.42
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.48
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.17
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.15
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.61
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 2.12
- Rat (Acute)
- 2.02
- Rat (Chronic Oral)
- 2.91
- Fathead Minnow
- 3.8
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 333.02
- Hydration Free Energy
- -12.19
- Log(D) at pH=7.4
- -2.12
- Log(P)
- 0.47
- Log S
- -0.32
- Log(Vapor Pressure)
- -5.57
- Melting Point
- 168.85
- pKa Acid
- 5.91
- pKa Basic
- 5.09
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.9018 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8929 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8911 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8844 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.8812 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8741 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8694 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8652 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 3 | 0.8530 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.8520 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8444 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.8356 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8339 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8314 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8312 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.8281 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8228 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.8093 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8058 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7976 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7930 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.7850 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7813 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7794 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 3 | 0.7738 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7729 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7714 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7685 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7565 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7539 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7526 |
| Carboxyethyl-arginine beta-lactam-synthase | P0DJQ7 | BLS_STRCL | Streptomyces clavuligerus | 3 | 0.7452 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 3 | 0.7441 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7419 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7415 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7393 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7380 |
| uroporphyrinogen-III C-methyltransferase | P95417 | P95417_PSEAI | Pseudomonas aeruginosa | 3 | 0.7376 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7373 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7353 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7349 |
| Ribosomal RNA large subunit methyltransferase H | P0C1V0 | RLMH_STAAU | Staphylococcus aureus | 3 | 0.7339 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7315 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7315 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7300 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7298 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7285 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7272 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7266 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7242 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7242 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7216 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7200 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7190 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7179 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7175 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7170 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 3 | 0.7104 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7070 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | P62617 | ISPF_ECOLI | Escherichia coli | 4 | 0.7069 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7064 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7061 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7051 |
| Glutamate receptor 3 | P19492 | GRIA3_RAT | Rattus norvegicus | 3 | 0.7046 |
| Cytosol aminopeptidase | P00727 | AMPL_BOVIN | Bos taurus | 2 | 0.7022 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7020 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7002 |