P-hydroxybenzoic acid - Compound Card

P-hydroxybenzoic acid

Select a section from the left sidebar

P-hydroxybenzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Asparagaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzoic Acid Derivative
Canonical Smiles Oc1ccc(cc1)C(=O)O
InChI InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
InChIKey FJKROLUGYXJWQN-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 Parmentiera cereifera Bignoniaceae Plantae 163100
2 Pteranthus dichotomus Caryophyllaceae Plantae 325512
3 Helianthemum sessiliflorum Cistaceae Plantae 2650562
4 Anastatica hierochuntica Cruciferae-Brassicaceea Plantae 663965
5 Ephedra aphylla Ephedraceae Plantae 191304
6 Oligomeris linifolia Resedaceae Plantae 265230
7 Achyranthes aspera Amaranthaceae Plantae 240005
8 Dracaena mannii Asparagaceae Plantae 1237547

Showing of synonyms

  • 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]
  • Anigboro AA, Akeghware O, et al. (2022). Evaluation of bioactive constituents and In vitro antioxidant potentials of the ethanolic leaf extracts of Dracaena mannii, Euphorbia hirta and Senna alata. Journal of bio-research, 2022, 20(3), 1753-1762. [View]
  • Hussein SAM, Barakat HH, et al. (1997). Flavonoids from Ephedra aphylla. Phytochemistry,1997,45(7),1529-1532. [View]
  • Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
  • Nakashima S, Matsuda H, et al. (2010). Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic and Medicinal Chemistry,2010,18(6),2337-2345. [View] [PubMed]
  • Atta EM, Nassar AA, et al. (2013). New flavonoid glycoside and pharmacological activities of Pteranthus dichotomus Forssk.. Records of Natural Products,2013,7(2),69-79. [View]
  • Abdel-Wahab NM, Hamed ANE, et al. (2014). Phenolic acid glycosides from Parmentiera cereifera Seem. (Candle tree). Phytochemistry Letters,2014,9,74-77. [View]
  • Hussein SR, Elkhateeb A, et al. (2013). Phytochemical investigation of Oligomeris linifolia (Vahl) Macbr. (Resedaceae). Biochemical Systematics and Ecology,2013,49,73-76. [View]
Pubchem: 135
Kegg Ligand: C00156
Chebi: 30763
Nmrshiftdb2: 10024827
Metabolights: MTBLC30763
Drugbank: DB04242
Pdb Ligand: PHB
Bindingdb: 26194
CPRiL: 11241
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 138.12 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.030
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
27.04
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
5.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.050
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
1.260
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
2.050
Micronucleos
Safe
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
2.080
Rat (Acute)
1.950
Rat (Chronic Oral)
2.830
Fathead Minnow
3.840
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
303.220
Hydration Free Energy
-9.880
Log(D) at pH=7.4
-1.400
Log(P)
1.55
Log S
-1.82
Log(Vapor Pressure)
-4.62
Melting Point
249.12
pKa Acid
5.07
pKa Basic
-2.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9658
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9658
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9556
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9556
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9493
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9493
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9464
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9464
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9371
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9371
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.9340
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.9340
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9275
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9275
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9261
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9261
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9187
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.9187
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.9129
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.9129
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9045
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9045
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8981
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8981
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8946
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8946
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8938
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8938
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8861
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8861
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8765
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8765
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 3 0.8660
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 3 0.8660
Chorismate pyruvate-lyase P26602 UBIC_ECOLI Escherichia coli 3 0.8627
Chorismate pyruvate-lyase P26602 UBIC_ECOLI Escherichia coli 3 0.8627
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8588
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8588
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8550
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8550
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8456
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8456
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8411
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8411
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8099
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8099
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7954
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7954
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7874
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7874
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7759
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7759
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7749
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7749
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7742
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7742
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7721
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7721
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7468
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7468
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7444
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7444
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7367
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7367
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7363
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7363
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7342
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7342
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7337
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7337
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7330
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7330
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7321
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7321
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7320
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7320
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7311
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7311
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7301
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7301
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7300
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7300
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7252
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7252
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7246
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7246
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7241
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7241
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7209
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7192
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7192
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7175
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7175
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7144
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7144
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7135
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7135
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7133
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7133
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7105
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7105
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7092
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7092
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7080
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7080
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7078
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7078
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7064
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7064
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7053
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7053
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7045
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7045
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7039
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7039
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7032
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7032
p-hydroxybenzoate hydroxylase P00438 PHHY_PSEFL Pseudomonas fluorescens 3 0.7030
p-hydroxybenzoate hydroxylase P00438 PHHY_PSEFL Pseudomonas fluorescens 3 0.7030
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7018
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7018
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7008
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7008
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004

Download SDF