3,4’-diacetoxy-5-methoxy-2-prenylsrilbene - Compound Card

3,4’-diacetoxy-5-methoxy-2-prenylsrilbene

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3,4’-diacetoxy-5-methoxy-2-prenylsrilbene

Structure
Zoomed Structure
  • Family: Plantae - Cyperaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylflavone
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)OC(=O)C)c(c(c1)OC(=O)C)CC=C(C)C
InChI InChI=1S/C24H26O5/c1-16(2)6-13-23-20(14-22(27-5)15-24(23)29-18(4)26)10-7-19-8-11-21(12-9-19)28-17(3)25/h6-12,14-15H,13H2,1-5H3/b10-7+
InChIKey LZIUYSGUPSFZOH-JXMROGBWSA-N
Formula C24H26O5
HBA 5
HBD 0
MW 394.47
Rotatable Bonds 7
TPSA 61.83
LogP 5.22
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 394.18
Number of Lipinski Rule Violations 1
# 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]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 394.47 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 394.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
43.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.500
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.820
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.370
Micronucleos
Safe
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
-6.340
Rat (Acute)
2.050
Rat (Chronic Oral)
2.300
Fathead Minnow
5.700
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
444.440
Hydration Free Energy
-5.520
Log(D) at pH=7.4
4.210
Log(P)
5.9
Log S
-6.61
Log(Vapor Pressure)
-6.91
Melting Point
123.64
pKa Acid
12.16
pKa Basic
6.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9434
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9250
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9176
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9095
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8964
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8786
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8770
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8740
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8701
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8692
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8658
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8638
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8620
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8531
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8492
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8429
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8412
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8383
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8313
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8312
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8286
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8260
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8252
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8223
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8159
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8123
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8086
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8079
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8076
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8032
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8015
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8006
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7965
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7901
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7866
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7852
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7843
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7810
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7789
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7784
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7773
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7679
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7672
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7670
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7649
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7618
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7581
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7562
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7532
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7528
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7526
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7509
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7495
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7495
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7491
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7490
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7482
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7481
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7468
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7446
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7443
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7395
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7394
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7393
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7388
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7377
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7370
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7368
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7364
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7351
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7325
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7322
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7307
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7307
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7303
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7300
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7295
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7279
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7267
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7263
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7252
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7248
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7240
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7240
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7237
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7235
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7222
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7222
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7218
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7215
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7212
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7206
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7205
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7205
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7203
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7200
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7197
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7193
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7190
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7185
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7181
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7176
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 2 0.7173
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7169
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7153
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7146
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7143
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7141
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7139
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7139
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7129
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7125
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7124
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7112
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7106
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7104
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7097
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7094
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7090
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7084
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7079
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7077
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7074
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7046
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7045
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7041
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7041
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7032
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7031
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7030
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7028
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7027
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7022
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7019
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7009
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7000

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