delta-Viniferin

Details

• Internal ID: 2bd99670-5a8a-4a2a-bc3a-201c2ec7acd9
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=CC4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
• InChI: InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m1/s1
• InChI Key: LILPTCHQLRKZNG-CKKRXTSSSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₆
• Molecular Weight: 454.50 g/mol
• Exact Mass: 454.14163842 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.65
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• delta-viniferin
• trans-delta-viniferin-A
• (2R,3R)-trans-delta-viniferin
• 204076-78-8
• CHEMBL4209546
• SCHEMBL17995572
• CHEBI:76147
• 5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]benzene-1,3-diol
• Q5254535
• (2R)-2beta-(4-Hydroxyphenyl)-3alpha-(3,5-dihydroxyphenyl)-5-(3,5-dihydroxystyryl)-2,3-dihydrobenzofuran
• 1,3-benzenediol, 5-[(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-2,3-dihydro-2-(4-hydroxyphenyl)-5-benzofuranyl]ethenyl]-
• 5-[(2R,3R)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• InChI=1/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m1/s
• rel-5-{(E)-2-[(2R,3R)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]vinyl}benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	-	0.7727	77.27%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4875	48.75%
OATP2B1 inhibitior	+	0.5650	56.50%
OATP1B1 inhibitior	+	0.8003	80.03%
OATP1B3 inhibitior	-	0.2406	24.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6814	68.14%
P-glycoprotein inhibitior	+	0.6012	60.12%
P-glycoprotein substrate	-	0.9472	94.72%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	+	0.6202	62.02%
CYP2D6 substrate	+	0.3681	36.81%
CYP3A4 inhibition	+	0.5901	59.01%
CYP2C9 inhibition	+	0.9088	90.88%
CYP2C19 inhibition	+	0.8471	84.71%
CYP2D6 inhibition	-	0.8727	87.27%
CYP1A2 inhibition	+	0.9282	92.82%
CYP2C8 inhibition	+	0.7971	79.71%
CYP inhibitory promiscuity	+	0.9725	97.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.3539	35.39%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.5088	50.88%
Skin irritation	+	0.5230	52.30%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7907	79.07%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5400	54.00%
skin sensitisation	-	0.6951	69.51%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.6295	62.95%
Acute Oral Toxicity (c)	III	0.4075	40.75%
Estrogen receptor binding	+	0.6338	63.38%
Androgen receptor binding	+	0.7906	79.06%
Thyroid receptor binding	+	0.7073	70.73%
Glucocorticoid receptor binding	+	0.7180	71.80%
Aromatase binding	+	0.6319	63.19%
PPAR gamma	+	0.8219	82.19%
Honey bee toxicity	-	0.6989	69.89%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.60%	91.11%
CHEMBL3194	P02766	Transthyretin	93.34%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	92.59%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.42%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.72%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.44%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.87%	94.45%
CHEMBL242	Q92731	Estrogen receptor beta	85.76%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.44%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.67%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.00%	91.71%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 637098
• NPASS: NPC154362
• LOTUS: LTS0087137
• wikiData: Q5254535