4-hydroxyl-5-methylcoumarin - Compound Card

4-hydroxyl-5-methylcoumarin

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4-hydroxyl-5-methylcoumarin

Structure
Zoomed Structure
  • Family: Plantae - Ebenaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles O=c1cc(O)c2c(o1)cccc2C
InChI InChI=1S/C10H8O3/c1-6-3-2-4-8-10(6)7(11)5-9(12)13-8/h2-5,11H,1H3
InChIKey SGMVRLBDQDWGRZ-UHFFFAOYSA-N
Formula C10H8O3
HBA 3
HBD 1
MW 176.17
Rotatable Bonds 0
TPSA 50.44
LogP 1.81
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 176.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Diospyros bipindensis Ebenaceae Plantae 413723

Showing of synonyms

  • Cesari I, Queiroz EF, et al. (2013). Extensive phytochemical investigation of the polar constituents of Diospyros bipindensis Gürke traditionally used by Baka pygmies.. Phytochemistry,2013, 96, 279-287. [View] [PubMed]
Pubchem: 54688203
Nmrshiftdb2: 60049873

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 176.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.1
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.94
Plasma Protein Binding
58.81
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.85
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.68
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
3.69
Rat (Acute)
2.03
Rat (Chronic Oral)
2.07
Fathead Minnow
3.93
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
326.5
Hydration Free Energy
-9.74
Log(D) at pH=7.4
1.8
Log(P)
1.34
Log S
-2.6
Log(Vapor Pressure)
-4.24
Melting Point
163.5
pKa Acid
4.38
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.9821
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9513
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9422
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9255
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9227
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9216
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9211
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9180
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9152
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9093
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.9077
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.8992
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8983
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8890
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8879
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8786
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8769
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8538
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8475
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8470
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.8235
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 3 0.8055
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8051
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7954
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7765
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7753
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7742
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7736
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7709
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7609
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7574
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7565
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7539
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7519
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7507
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7506
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7493
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 3 0.7483
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7480
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7468
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7461
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7390
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7386
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7352
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7331
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7300
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7281
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7252
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7243
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7238
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7192
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7188
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7162
Uricase Q00511 URIC_ASPFL Aspergillus flavus 3 0.7160
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7141
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7141
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7124
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7117
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7115
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7061
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7049
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 3 0.7043
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7025
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7019
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7012

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