3,4’-dihydroxy-5-methoxy-2-prenylstilbene - Compound Card

3,4’-dihydroxy-5-methoxy-2-prenylstilbene

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3,4’-dihydroxy-5-methoxy-2-prenylstilbene

Structure
Zoomed Structure
  • Family: Plantae - Cyperaceae
  • Kingdom: Plantae
  • Class: Stilbene
    • Subclass: Prenylated Stilbene
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)O)c(c(c1)O)CC=C(C)C
InChI InChI=1S/C20H22O3/c1-14(2)4-11-19-16(12-18(23-3)13-20(19)22)8-5-15-6-9-17(21)10-7-15/h4-10,12-13,21-22H,11H2,1-3H3/b8-5+
InChIKey SIBQNRICTJZQSR-VMPITWQZSA-N
Formula C20H22O3
HBA 3
HBD 2
MW 310.39
Rotatable Bonds 5
TPSA 49.69
LogP 4.79
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 310.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Schoenus nigricans Cyperaceae Plantae 76506

Showing of synonyms

  • Dawidar A, Jakupovic J, et al. (1994). Prenylstilbenes and prenylflavanones from Schoenus nigricans.. Phytochemistry, 1994, 36(3), 803-806. [View]
Pubchem: 101665864
Nmrshiftdb2: 70078990

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 310.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 310.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
46.83
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.300
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.410
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.180
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
3.970
Rat (Acute)
1.690
Rat (Chronic Oral)
2.670
Fathead Minnow
5.080
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
404.510
Hydration Free Energy
-8.250
Log(D) at pH=7.4
4.060
Log(P)
5.72
Log S
-5.75
Log(Vapor Pressure)
-6.69
Melting Point
130.99
pKa Acid
10.56
pKa Basic
7.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9650
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9594
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9585
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9555
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9551
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9440
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9357
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9345
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9230
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9222
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.9184
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9019
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9017
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8988
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8967
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8891
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8848
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8833
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8816
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.8801
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8785
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8775
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8760
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8682
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8677
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8558
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8545
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8504
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8379
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8351
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8277
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8242
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8227
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.8195
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8189
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8175
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8152
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8130
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8093
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8064
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8015
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8010
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7970
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7954
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7906
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 4 0.7896
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7859
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7841
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7772
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7757
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7747
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7738
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7722
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7696
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7695
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7685
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7677
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7646
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7631
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7617
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7584
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7579
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7573
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7560
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7546
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7533
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7495
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7490
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7474
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7473
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7463
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7463
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7459
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7457
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7434
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7420
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7420
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7417
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7404
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7396
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7387
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7386
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7371
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7367
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7362
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7346
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7345
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7324
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7312
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7310
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7304
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7302
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 4 0.7293
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7293
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7286
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7281
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7257
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7247
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7244
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7241
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7239
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7236
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7234
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7233
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7228
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7220
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7196
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7176
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7174
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7155
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7144
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7135
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7098
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7097
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7089
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7087
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7080
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7077
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7075
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7066
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7062
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7057
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7053
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7052
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7045
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7036
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7034
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7022
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7022
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7015
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7013
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7012
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7012
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7008
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7002

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