Methyl 4-hydroxybenzoate - Compound Card

Methyl 4-hydroxybenzoate

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Methyl 4-hydroxybenzoate

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Fungi, Plantae
  • Class: Phenolic
    • Subclass: Hydroxybenzoate Ester
Canonical Smiles COC(=O)c1ccc(cc1)O
InChI InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChIKey LXCFILQKKLGQFO-UHFFFAOYSA-N
Formula C8H8O3
HBA 3
HBD 1
MW 152.15
Rotatable Bonds 1
TPSA 46.53
LogP 1.18
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 152.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Nigrospora sphaerica Trichosphaeriaceae Fungi 114231
2 Senecio roseiflorus Asteraceae Plantae 1886451
3 Ficus thonningii Moraceae Plantae 309310
4 Chaetomium sp. Chaetomiaceae Fungi 1769349

Showing of synonyms

  • Kerubo LO, Midiwo JO, et al. (2013). Antiplasmodial activity of compounds from the surface exudates of Senecio roseiflorus. Natural Product Communications,2013,8(2),175-176. [View] [PubMed]
  • Ancheeva E, Küppers L, et al. (2017). Expanding the Metabolic Profile of the Fungus Chaetomium sp. through Co-culture with Autoclaved Pseudomonas aeruginosa. Eur. J. Org. Chem., 2017(22), 3256-3264. [View]
  • Metwaly AM, Kadry HA, et al. (2014). Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochemistry Letters,2014,7,1-5. [View]
  • Ango PY, Kapche DW, et al. (2016). Thonningiiflavanonol A and thonningiiflavanonol B, two novel flavonoids, and other constituents of Ficus thonningii Blume (Moraceae).. Zeitschrift fur Naturforschung. C, Journal of biosciences,2016, 71(3-4), 65-71. [View] [PubMed]
Pubchem: 7456
Chebi: 31835
Nmrshiftdb2: 10008850
Metabolights: MTBLC31835
Drugbank: DB14212
Pdb Ligand: MPB
Bindingdb: 50209100
CPRiL: 8976
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 152.15 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.020
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.380
Plasma Protein Binding
12.29
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
7.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.810
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
1.050
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.490
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
3.480
Rat (Acute)
1.880
Rat (Chronic Oral)
2.450
Fathead Minnow
3.940
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
269.600
Hydration Free Energy
-9.650
Log(D) at pH=7.4
2.010
Log(P)
1.91
Log S
-2.1
Log(Vapor Pressure)
-2.45
Melting Point
114.82
pKa Acid
8.33
pKa Basic
-0.26
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 0.9665
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9665
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9584
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9584
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9512
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9512
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9243
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9243
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9005
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9005
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8700
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8700
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8672
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8672
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7929
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7929
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7918
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7918
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7869
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7869
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7840
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7840
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7680
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7680
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7590
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7590
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7550
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7550
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7543
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7543
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7537
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7537
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7519
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7519
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7459
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7459
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7455
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7455
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7450
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7450
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7433
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7433
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7408
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7408
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7376
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7376
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7357
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7357
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7349
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7349
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7348
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7348
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7331
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7331
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7285
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7285
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 2 0.7264
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 2 0.7264
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7258
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7258
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7256
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7256
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7239
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7239
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7232
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7232
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7199
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7199
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7196
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7196
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7191
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7191
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7189
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7189
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7177
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7177
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7169
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7169
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7168
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7168
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7154
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7154
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7148
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7148
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7145
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7145
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7142
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7142
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7134
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7134
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7119
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7119
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7101
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7101
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7095
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7095
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7057
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7057
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7056
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7056
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7044
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7044
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 2 0.7043
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 2 0.7043
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7040
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7040
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7040
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7040
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7038
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7038
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7030
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7022
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7022
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7021
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7021
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7020
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7020
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7008
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7008
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7008
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7008
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7006
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7006
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7001
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7001

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