4-hydroxy-3,5-dimethylbenzoic acid - Compound Card

4-hydroxy-3,5-dimethylbenzoic acid

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4-hydroxy-3,5-dimethylbenzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC(=O)c1cc(C)c(c(c1)C)O
InChI InChI=1S/C9H10O3/c1-5-3-7(9(11)12)4-6(2)8(5)10/h3-4,10H,1-2H3,(H,11,12)
InChIKey OMNHTTWQSSUZHO-UHFFFAOYSA-N
Formula C9H10O3
HBA 2
HBD 2
MW 166.18
Rotatable Bonds 1
TPSA 57.53
LogP 1.71
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 166.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ekebergia senegalensis Meliaceae Plantae 124949

Showing of synonyms

  • Kemayou GPM, Happi GM, et al. (2021). Senegalin, a new phenylpropanoid and other secondary metabolites from the stem bark of Ekebergia senegalensis A. Juss. (Meliaceae).. Natural product research,2021, 35(21), 3694-3700. [View] [PubMed]
Pubchem: 138387
Nmrshiftdb2: 20208849

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 166.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.35
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
30.77
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
10.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.09
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
2.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
1.65
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
2.5
Rat (Acute)
2.33
Rat (Chronic Oral)
2.92
Fathead Minnow
3.73
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
293.33
Hydration Free Energy
-9.12
Log(D) at pH=7.4
0.02
Log(P)
2.47
Log S
-2.44
Log(Vapor Pressure)
-4.77
Melting Point
207.63
pKa Acid
4.16
pKa Basic
3.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9715
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9584
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9527
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9430
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9426
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9371
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9370
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 4 0.9307
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9292
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9185
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.9056
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.9032
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9023
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9020
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8943
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8768
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.8732
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8683
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8637
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8562
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.8466
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8365
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8295
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8262
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8250
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8051
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.8049
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.8046
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8020
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8019
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8008
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7903
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7776
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7773
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7766
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7683
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7670
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7636
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7632
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7460
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7433
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7381
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7379
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7377
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7310
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7242
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7239
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7238
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7172
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7151
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7137
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7132
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7059
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7053
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7036
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7016
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7013

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