1-{2-hydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-2H-1-benzopyran-2-one - Compound Card

1-{2-hydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-2H-1-benzopyran-2-one

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1-{2-hydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-2H-1-benzopyran-2-one

Structure
Zoomed Structure
  • Family: Plantae - Dipterocarpaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Stilbene-Coumarin Derivative
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)O)c2c(c1)oc(=O)c(c2OC)C
InChI InChI=1S/C20H18O5/c1-12-19(24-3)18-14(7-4-13-5-8-15(21)9-6-13)10-16(23-2)11-17(18)25-20(12)22/h4-11,21H,1-3H3/b7-4+
InChIKey CEMLQZUSSLCRBU-QPJJXVBHSA-N
Formula C20H18O5
HBA 5
HBD 1
MW 338.36
Rotatable Bonds 4
TPSA 68.9
LogP 3.99
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 338.12
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: 10088489
Nmrshiftdb2: 70081162

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 338.36 g/mol

Structure

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

Level: 0

Mol. Weight: 338.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.36 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.560
Plasma Protein Binding
76.83
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
4.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.530
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.890
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
2.380
Rat (Acute)
2.000
Rat (Chronic Oral)
2.000
Fathead Minnow
5.320
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
461.860
Hydration Free Energy
-9.110
Log(D) at pH=7.4
3.700
Log(P)
4.37
Log S
-6.12
Log(Vapor Pressure)
-7.74
Melting Point
184.97
pKa Acid
8.4
pKa Basic
4.58
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 0.9791
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9780
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9601
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9543
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9542
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9386
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9308
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9300
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9237
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9229
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9178
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.9006
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8995
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8993
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8954
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8949
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8855
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8807
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8687
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8680
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8680
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8625
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8546
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8538
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8468
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8432
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8431
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8416
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8345
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8300
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8299
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8268
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8248
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8240
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8213
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8203
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8147
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8140
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8130
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8127
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8105
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8091
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8083
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8053
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8044
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7971
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7943
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7882
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7852
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7851
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7795
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7781
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7762
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7748
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7730
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7728
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7726
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7703
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7692
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7685
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7644
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7626
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7622
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7616
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7604
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7601
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7590
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7585
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7585
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7585
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7554
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7552
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7523
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7512
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7503
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7481
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7468
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7456
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7441
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7429
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7413
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7409
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7403
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7396
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7386
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7376
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7334
Endoplasmic reticulum aminopeptidase 2 Q6P179 ERAP2_HUMAN Homo sapiens 2 0.7327
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7319
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7315
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7310
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7305
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7300
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7296
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7290
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7280
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7270
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7262
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7254
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7238
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7216
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7210
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7205
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7198
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7189
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7170
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7130
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7122
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7121
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7117
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7114
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7113
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7108
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7101
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7100
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7098
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7090
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7076
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7071
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7070
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7062
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7057
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7047
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7037
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7036
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7034
Flavonoid 3-O-glucosyltransferase A6XNC6 UGFGT_MEDTR Medicago truncatula 2 0.7031
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7029
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7027
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7010
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7004

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