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3,4-dihydroxybenzoic acid
- Family: Plantae - Ranunculaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | OC(=O)c1cccc(c1O)O |
|---|---|
| InChI | InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) |
| InChIKey | GLDQAMYCGOIJDV-UHFFFAOYSA-N |
| Formula | C7H6O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 154.12 |
| Rotatable Bonds | 1 |
| TPSA | 77.76 |
| LogP | 0.8 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 154.03 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ranunculus macrophyllus | Ranunculaceae | Plantae | 286909 |
Showing of synonyms
3,4-dihydroxybenzoic acid
2,3-Dihydroxybenzoic acid
303-38-8
Pyrocatechuic acid
O-Pyrocatechuic acid
Benzoic acid, 2,3-dihydroxy-
2-Pyrocatechuic acid
3-Hydroxysalicylic acid
DOBK
2,3-Dihydroxybenzoicacid
DHBA
Catecholcarboxylic acid
Dihydroxybenzoic acid
2,3-DIHYDROXY-BENZOIC ACID
2,3 DHB
MFCD00002446
Catechol-3-carboxylic acid
2,3-dihydroxy benzoic acid
27138-57-4
2,3-DIHDROXYBENZOIC ACID
CHEBI:18026
70D5FBB392
NSC-27435
Resorcylic acid
Benzoic acid, dihydroxy-
EINECS 206-139-5
NSC 27435
BRN 2209117
Pyrocatechuate
UNII-70D5FBB392
O-Pyrocatechuate
Catecholcarboxylate
1l6m
3tf6
3u0d
Spectrum2_001086
Spectrum3_001819
Benzoic acid,3-dihydroxy-
2,3 Dihydroxy-benzoic acid
2,3-Dihydroxybenzoate, IV
CHEMBL1432
SCHEMBL37458
BSPBio_003437
4-10-00-01414 (Beilstein Handbook Reference)
MLS001066375
SPBio_001132
Pyrocatechol-3-carboxylic Acid
BDBM92456
KBio3_002940
DTXSID70858712
2,3-Dihydroxybenzoic acid, 99%
HMS2231J14
HMS3369A12
KUC106698N
HY-Y0202
NSC27435
CCG-40337
AKOS009156763
AC-2985
CS-W019844
DB01672
FD00785
PS-3013
SDCCGMLS-0066859.P001
NCGC00178064-01
BP-12659
KSC-11-207-9
SMR000471836
SY003494
DB-027090
NS00009040
S4946
1,2-DIHYDROXYBENZENE-3-CARBOXYLIC ACID
C00196
EN300-112276
SR-01000761414
Q2823200
SR-01000761414-2
Z367679198
FF124556-A828-490B-B324-9AE859B695FA
InChI=1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11
- Deghima A, Righi N, et al. (2019). Bioactive polyphenols from Ranunculus macrophyllus Desf Roots:Quantification, identification and antioxidant activity. South African Journal of Botany, 2019, 123, 208-213. [View]
Pubchem:
19
Cas:
303-38-8
Gnps:
CCMSLIB00000426907
Zinc:
ZINC000000388166
Kegg Ligand:
C00196
Chebi:
18026
Nmrshiftdb2:
20035558
Metabolights:
MTBLC18026
Chembl:
CHEMBL1432
Comptox:
DTXSID70858712
Drugbank:
DB01672
Pdb Ligand:
DBH
Bindingdb:
92456
CPRiL:
35719
SMILES: c1ccccc1
Level: 0
Mol. Weight: 154.12 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.28
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.69
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- 18.39
- 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
- Non-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
- 8.22
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.46
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.25
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.9
- 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
- 1.97
- Rat (Acute)
- 2.04
- Rat (Chronic Oral)
- 3.45
- Fathead Minnow
- 3.81
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 317.82
- Hydration Free Energy
- -11.69
- Log(D) at pH=7.4
- -1.51
- Log(P)
- 1.23
- Log S
- -1.09
- Log(Vapor Pressure)
- -5.12
- Melting Point
- 184.76
- pKa Acid
- 3.64
- pKa Basic
- 1.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.9208 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9181 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9178 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9114 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.9005 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8992 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8976 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8826 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8747 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8658 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8644 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8634 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8550 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8523 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.8452 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.8355 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8156 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 3 | 0.8130 |
| Carbonic anhydrase 5A, mitochondrial | P23589 | CAH5A_MOUSE | Mus musculus | 3 | 0.8128 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8087 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8057 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8042 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7931 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7900 |
| 4-substituted benzoates-glutamate ligase GH3.12 | Q9LYU4 | GH312_ARATH | Arabidopsis thaliana | 3 | 0.7790 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7787 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7774 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7763 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7707 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7685 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 3 | 0.7647 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7589 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7579 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7573 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7561 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7534 |
| 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase | Q988D3 | Q988D3_RHILO | Mesorhizobium japonicum) | 3 | 0.7492 |
| Uridine phosphorylase | Q9KT71 | Q9KT71_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7482 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.7464 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7427 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7425 |
| Ribosome-inactivating protein 3 | P25891 | RIP3_MAIZE | Zea mays | 3 | 0.7409 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7408 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 4 | 0.7338 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7306 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7288 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7269 |
| Uncharacterized protein | Q3F0V8 | Q3F0V8_BACTI | Bacillus thuringiensis serovar israelensis ATCC 35646 | 3 | 0.7262 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7244 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.7242 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7241 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7205 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7202 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7197 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7195 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7182 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7181 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7160 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7145 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7145 |
| L-methionine gamma-lyase | P13254 | MEGL_PSEPU | Pseudomonas putida | 3 | 0.7133 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7130 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7124 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7111 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7109 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7095 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7091 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7089 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7089 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 3 | 0.7074 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7054 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7036 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7027 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7022 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7009 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7005 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7001 |