Epsilon-viniferin - Compound Card

Epsilon-viniferin

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Epsilon-viniferin

Structure
Zoomed Structure
  • Family: Plantae - Vitaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles Oc1ccc(cc1)/C=C/c1cc(O)cc2c1[C@@H](c1cc(O)cc(c1)O)[C@@H](O2)c1ccc(cc1)O
InChI InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1
InChIKey FQWLMRXWKZGLFI-YVYUXZJTSA-N
Formula C28H22O6
HBA 6
HBD 5
MW 454.48
Rotatable Bonds 4
TPSA 110.38
LogP 5.65
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 454.14
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cyphostemma crotalarioides Vitaceae Plantae 178803

Showing of synonyms

  • Ducrot PH, Koilmann A, et al. (1998). Cyphostemmins A-B, two new antifungal oligostilbenes from Cyphostemma crotalarioides (Vitaceae). Tetrahedron Letters,1998,39(52),9655-9658. [View]
Pubchem: 5281728
Kegg Ligand: C10289
Chebi: 10556
Nmrshiftdb2: 60027416
Metabolights: MTBLC10556
Bindingdb: 50531887
CPRiL: 79247
Structure

SMILES: c1ccccc1C=Cc2cccc(c23)OC(c4ccccc4)C3c5ccccc5

Level: 3

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1ccccc1C=Cc2cccc(c23)OC(C3)c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C2c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3

Level: 1

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1cccc(c12)OCC2c3ccccc3

Level: 1

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 454.48 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 454.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 454.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.63
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.980
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.390
Plasma Protein Binding
97.95
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.230
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.710
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.120
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.270
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-350.020
Rat (Acute)
2.040
Rat (Chronic Oral)
3.130
Fathead Minnow
6.580
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
588.000
Hydration Free Energy
-3.390
Log(D) at pH=7.4
3.320
Log(P)
5.1
Log S
-4.69
Log(Vapor Pressure)
-12.38
Melting Point
301.75
pKa Acid
8.58
pKa Basic
9.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9327
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9327
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9199
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9199
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9007
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9007
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8977
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8977
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8959
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8959
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8878
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8878
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8555
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8555
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8536
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8536
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8360
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8360
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8312
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8312
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8304
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8304
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8302
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8302
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8285
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8285
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8282
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8282
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8269
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8269
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8225
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8225
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8157
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8157
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8059
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8059
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8005
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8005
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7860
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7860
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7784
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7784
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7716
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7716
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7711
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7711
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7700
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7700
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7675
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7675
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7626
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7626
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7534
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7534
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7525
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7525
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7518
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7518
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7509
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7509
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7477
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7477
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7462
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7462
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7461
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7461
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7447
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7447
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7434
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7434
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7426
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7426
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7420
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7420
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7383
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7383
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7371
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7371
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7352
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7352
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7272
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7272
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7212
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7212
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7203
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7203
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7199
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7199
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7198
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7198
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7193
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7193
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7185
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7185
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 3 0.7171
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 3 0.7171
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7163
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7163
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7131
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7131
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 3 0.7126
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 3 0.7126
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7076
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7076
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7067
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7067
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7044
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7044
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7020
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7020

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