3,5-dimethoxy-4'-hydroxystilbene - Compound Card

3,5-dimethoxy-4'-hydroxystilbene

Select a section from the left sidebar

3,5-dimethoxy-4'-hydroxystilbene

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Stilbenoid
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)O)cc(c1)OC
InChI InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
InChIKey VLEUZFDZJKSGMX-ONEGZZNKSA-N
Formula C16H16O3
HBA 3
HBD 1
MW 256.3
Rotatable Bonds 4
TPSA 38.69
LogP 3.58
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 256.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Guibourtia tessmannii Leguminosae/Fabaceae Plantae 327904

Showing of synonyms

  • Fuendjiep V, Wandji J, et al. (2002). Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.. Phytochemistry,2002, 60(8), 803-806. [View] [PubMed]
Pubchem: 5281727
Kegg Ligand: C10287
Chebi: 8630
Nmrshiftdb2: 60015865
Metabolights: MTBLC8630
Drugbank: DB17939
Pdb Ligand: 3RL
Bindingdb: 50131688
CPRiL: 292621
Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 256.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 256.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.340
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
55.51
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.070
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.860
Micronucleos
Safe
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
4.270
Rat (Acute)
1.680
Rat (Chronic Oral)
2.310
Fathead Minnow
4.840
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
378.890
Hydration Free Energy
-8.380
Log(D) at pH=7.4
3.750
Log(P)
4.22
Log S
-5.07
Log(Vapor Pressure)
-5.79
Melting Point
134.74
pKa Acid
10.45
pKa Basic
3.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9844
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9726
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9600
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9527
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.9433
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9401
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.9341
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9279
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.9212
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9171
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.9162
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.9153
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9140
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.9102
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9086
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8960
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8816
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8773
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8519
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8454
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8435
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8369
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8369
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8223
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8192
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8173
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8147
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7988
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7947
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7923
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7922
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7906
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7890
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7882
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7857
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7857
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7816
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7802
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7793
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7771
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7769
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7760
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7754
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7744
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7733
Methionine adenosyltransferase 2 subunit beta Q9NZL9 MAT2B_HUMAN Homo sapiens 4 0.7720
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7716
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7706
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7682
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7661
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7659
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7651
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7650
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7645
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7642
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7642
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7639
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7619
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7600
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7586
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7571
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7568
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7568
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 3 0.7561
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7560
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 4 0.7559
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7554
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7549
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7544
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7541
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7537
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7536
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7528
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7520
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 4 0.7517
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7509
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7506
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7497
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7496
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7479
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 2 0.7474
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7470
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7463
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7446
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7436
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7434
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 2 0.7427
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7413
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7411
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7405
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7397
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7381
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7373
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7371
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7364
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7362
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7355
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7350
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7350
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7340
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7339
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 2 0.7336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7330
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7308
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 3 0.7307
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7302
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7295
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7285
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7272
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7269
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7269
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7264
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7263
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7248
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7248
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7247
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7243
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7231
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7219
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7211
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7208
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7189
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7185
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7184
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7165
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7163
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7162
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7161
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7156
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7147
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7143
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7142
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7137
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7113
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7109
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7109
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7097
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7091
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7085
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7085
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 2 0.7074
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7074
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7074
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7058
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7057
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7055
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7052
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7050
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7048
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7047
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7037
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7035
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7027
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7026
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7025
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7024
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7023
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 3 0.7019
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7012
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7006
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7005

Download SDF