P-hydroxybenzoic acid - Compound Card

P-hydroxybenzoic acid

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P-hydroxybenzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Chenopodiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzoic Acid Derivative
Canonical Smiles OC(=O)c1ccccc1O
InChI InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChIKey YGSDEFSMJLZEOE-UHFFFAOYSA-N
Formula C7H6O3
HBA 2
HBD 2
MW 138.12
Rotatable Bonds 1
TPSA 57.53
LogP 1.09
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 10
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 138.03
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Harpephyllum caffrum Anacardiaceae Plantae 289712
2 Neurada procumbens Neuradaceae Plantae 32215
3 Coriandrum sativum Apiaceae Plantae 4047
4 Achyranthes aspera Amaranthaceae Plantae 240005
5 Trilepisium madagascariense Moraceae Plantae 241931
6 Bassia indica Chenopodiaceae Plantae 267517

Showing of synonyms

  • Othman A, Amen Y, et al. (2021). A novel acylated flavanol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica. Fitoterapia, 2021, 152, 104907. [View] [PubMed]
  • Ndhlala AR, Ghebrehiwot HM, et al. (2015). Antimicrobial, anthelmintic activities and characterisation of functional phenolic acids of Achyranthes aspera linn.: a medicinal plant used for the treatment of wounds and Ringworm in East Africa.. Frontiers in pharmacology,2015,6,274. [View] [PubMed]
  • Msaada K, Ben Jemia M, et al. (2014). Antioxidant activity of methanolic extracts from three coriander (Coriandrum sativum L.) fruit varieties. Arabian Journal of Chemistry,2014, in press. [View]
  • Nawwar M, Hussein S, et al. (2011). Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia,2011,82(8),1265-1271. [View] [PubMed]
  • Marzouk M, Hussein SR, et al. (2013). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Planta Medica,2013,79-PI46. [View]
  • Ango YP, Kapche GDWF, et al. (2016). Three New Derivatives and Others Constituents from the Roots and Twigs of Trilepisium madagascariense DC. Helvetica Chimica Acta, 2016, 99:642-649. [View]
Pubchem: 338
Kegg Ligand: C00805
Chebi: 16914
Nmrshiftdb2: 10008793
Metabolights: MTBLC16914
Chembl: CHEMBL424
Drugbank: DB00936
Pdb Ligand: SAL
Bindingdb: 26193
CPRiL: 6395
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 138.12 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.96
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
21.65
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.4
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.38
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.51
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
1.87
Rat (Acute)
2.28
Rat (Chronic Oral)
3.07
Fathead Minnow
3.87
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
281.63
Hydration Free Energy
-8.94
Log(D) at pH=7.4
-0.95
Log(P)
2.49
Log S
-1.68
Log(Vapor Pressure)
-4.3
Melting Point
162.06
pKa Acid
3.23
pKa Basic
-0.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.9047
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.9047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9039
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9039
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8754
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8754
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8646
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8646
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8555
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8555
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8469
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8469
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8305
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8305
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.8289
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.8289
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8272
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8272
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8086
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8086
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7935
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7935
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7893
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7893
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7849
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7849
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7841
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7841
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7836
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7836
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7778
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7778
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7771
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7771
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7758
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7758
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7666
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7666
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7657
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7657
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7646
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7646
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7620
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7620
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7598
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7598
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7552
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7552
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7511
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7511
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7474
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7474
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7434
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7434
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7427
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7427
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7390
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7390
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7351
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7351
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7317
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7317
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7294
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7294
Isochorismate pyruvate lyase Q51507 PCHB_PSEAE Pseudomonas aeruginosa 3 0.7240
Isochorismate pyruvate lyase Q51507 PCHB_PSEAE Pseudomonas aeruginosa 3 0.7240
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7220
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7220
3-oxoacyl-[acyl-carrier-protein] synthase 1 Q2YQQ9 Q2YQQ9_BRUA2 Brucella abortus 3 0.7206
3-oxoacyl-[acyl-carrier-protein] synthase 1 Q2YQQ9 Q2YQQ9_BRUA2 Brucella abortus 3 0.7206
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7201
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7201
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7192
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7192
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7176
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7176
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7153
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7153
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7151
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7151
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7134
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7134
3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI Escherichia coli 3 0.7124
3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI Escherichia coli 3 0.7124
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7114
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7114
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7100
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7100
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7099
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7099
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7097
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7097
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7080
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7080
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7080
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7080
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7073
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7073
Salicylate synthase P9WFX1 MBTI_MYCTU Mycobacterium tuberculosis 3 0.7058
Salicylate synthase P9WFX1 MBTI_MYCTU Mycobacterium tuberculosis 3 0.7058
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7057
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7057
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 2 0.7040
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 2 0.7040
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7039
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7039
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7027
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7027
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7009
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7009

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