5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7- dimethoxy-3-methyl-2H-1-benzopyran-2-one - Compound Card

5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7- dimethoxy-3-methyl-2H-1-benzopyran-2-one

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5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7- dimethoxy-3-methyl-2H-1-benzopyran-2-one

Structure
Zoomed Structure
  • Family: Dipterocarpaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Stilbene-Coumarin Derivative
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)O)c2c(c1)oc(=O)cc2OC
InChI InChI=1S/C19H16O5/c1-22-15-9-13(6-3-12-4-7-14(20)8-5-12)19-16(23-2)11-18(21)24-17(19)10-15/h3-11,20H,1-2H3/b6-3+
InChIKey RDPUQEDAFZNDBT-ZZXKWVIFSA-N
Formula C19H16O5
HBA 5
HBD 1
MW 324.33
Rotatable Bonds 4
TPSA 68.9
LogP 3.69
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.11
Exact Mass 324.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Monotes kerstingii Dipterocarpaceae Plantae 2029430

Showing of synonyms

  • Fotso GW, Mogue Kamdem L, et al. (2019). Antimicrobial secondary metabolites from the stem barks and leaves of Monotes kerstingii Gilg (Dipterocarpaceae).. Fitoterapia,2019, 137, 104239. [View] [PubMed]
Pubchem: 10358875
Nmrshiftdb2: 70081165

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2cccc(c23)oc(=O)cc3

Level: 1

Mol. Weight: 248.28 g/mol

Structure

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

Level: 0

Mol. Weight: 146.15 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
73.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.490
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.710
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.230
Rat (Acute)
1.880
Rat (Chronic Oral)
2.070
Fathead Minnow
5.220
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
457.500
Hydration Free Energy
-9.940
Log(D) at pH=7.4
3.450
Log(P)
3.77
Log S
-5.88
Log(Vapor Pressure)
-7.7
Melting Point
205.1
pKa Acid
8.38
pKa Basic
4.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9790
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9754
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9599
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9555
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9508
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9417
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9320
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9306
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9234
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9172
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8991
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8981
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8952
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8848
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8781
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8746
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8696
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8693
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8633
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8622
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8617
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8584
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8503
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8446
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8440
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8416
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8347
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8338
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8326
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8319
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8315
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8310
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8301
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8129
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8118
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8095
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8089
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8081
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8071
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8058
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8054
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7965
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7936
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7928
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7910
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7907
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7893
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7845
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7789
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7785
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7781
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7774
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7734
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7733
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7731
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7698
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7682
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7656
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7647
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7637
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7589
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7578
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 2 0.7576
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7568
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7566
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7517
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7515
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7504
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7493
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7486
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7483
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7482
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7473
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7472
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7462
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7457
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7455
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7444
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7440
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7431
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7420
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7331
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7327
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7314
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7310
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7299
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7288
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7270
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7267
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7258
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7247
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7246
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7231
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7227
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7213
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7212
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7201
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7198
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7195
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7188
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7184
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7180
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7173
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7171
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7148
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7126
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7121
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7121
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7117
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7116
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7115
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7108
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7099
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7095
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7085
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7074
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7074
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7063
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7056
Dihydrofolate reductase Q6FPH0 Q6FPH0_CANGA Candida glabrata 4 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7049
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7046
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7041
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7035
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7034
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7033
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7023
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7018
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7016
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7003
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7003
tRNA (guanine-N(1)-)-methyltransferase P43912 TRMD_HAEIN Haemophilus influenzae 4 0.7001

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