3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1→6)-beta-glucopyranoside)-stilbene - Compound Card

3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1→6)-beta-glucopyranoside)-stilbene

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3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1→6)-beta-glucopyranoside)-stilbene

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Stilbenoid
    • Subclass: Stilbene Glycoside
Canonical Smiles COc1cc(/C=C/c2ccc(cc2)O[C@H]2O[C@@H](CO[C@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)cc(c1)OC
InChI InChI=1S/C28H36O12/c1-14-21(29)23(31)25(33)27(38-14)37-13-20-22(30)24(32)26(34)28(40-20)39-17-8-6-15(7-9-17)4-5-16-10-18(35-2)12-19(11-16)36-3/h4-12,14,20-34H,13H2,1-3H3/b5-4+/t14-,20-,21-,22-,23+,24+,25+,26-,27-,28-/m0/s1
InChIKey NFEVXMANPKSNQD-CGLORVJSSA-N
Formula C28H36O12
HBA 12
HBD 6
MW 564.58
Rotatable Bonds 9
TPSA 176.76
LogP -0.1
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 564.22
Number of Lipinski Rule Violations 3
# 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]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2ccc(cc2)OC(O3)CCCC3COC4CCCCO4

Level: 3

Mol. Weight: 564.58 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 564.58 g/mol

Structure

SMILES: c1ccccc1C=Cc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 564.58 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 564.58 g/mol

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 564.58 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 564.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.25
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
85.75
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.710
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.610
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.480
Micronucleos
Toxic
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
-3670.000
Rat (Acute)
2.600
Rat (Chronic Oral)
3.960
Fathead Minnow
10.250
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
510.480
Hydration Free Energy
-2.920
Log(D) at pH=7.4
1.700
Log(P)
1.28
Log S
-3.61
Log(Vapor Pressure)
-11.78
Melting Point
172.21
pKa Acid
5.21
pKa Basic
2.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9831
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9732
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9691
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.9115
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9047
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8843
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8599
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8563
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8369
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8334
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8309
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8219
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8064
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8023
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7978
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7967
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7912
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7879
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7876
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7866
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7805
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7798
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7778
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7768
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7761
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7758
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7725
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7722
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7719
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7687
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7684
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7656
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7650
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7645
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7629
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7619
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7606
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7585
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 3 0.7585
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7576
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7565
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7549
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 2 0.7530
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 3 0.7526
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7507
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7504
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7493
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7492
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 3 0.7481
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7481
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7465
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7454
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7452
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7426
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7422
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7421
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7412
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7394
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7391
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7358
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7353
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7353
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7347
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 4 0.7344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7334
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7331
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7326
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7324
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7321
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7317
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7310
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7308
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7307
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7299
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7298
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7297
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7292
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 2 0.7284
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7280
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7275
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7271
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7269
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7263
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7253
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7246
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7246
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7242
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7241
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7241
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7237
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7228
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7217
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7215
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7214
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7211
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7206
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7203
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7192
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7192
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7192
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7176
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7170
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7170
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7168
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7165
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7160
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7158
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7152
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7142
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7141
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7135
LL-diaminopimelate aminotransferase, chloroplastic Q93ZN9 DAPAT_ARATH Arabidopsis thaliana 2 0.7134
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7130
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7125
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7124
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7124
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 2 0.7122
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7121
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7119
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7116
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7102
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 2 0.7101
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7099
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7096
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7090
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7085
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7083
Xanthine dehydrogenase/oxidase P22985 XDH_RAT Rattus norvegicus 2 0.7080
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7080
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7079
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7076
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7072
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7064
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7044
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7041
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7038
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7036
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7033
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7033
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7033
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7033
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7032
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7027
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7021
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7018
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7015
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7009
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7003
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7001

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