alpha-Viniferin

Details

• Internal ID: 88d97917-1307-4823-9a97-4caa684d72a2
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.12,5.110,13.021,25.09,27.017,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triol
• SMILES (Canonical): C1=CC(=CC=C1C2C3C4=C5C(C(OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=C8C(C(OC8=CC(=C7)O)C9=CC=C(C=C9)O)C1=C3C(=CC(=C1)O)O2)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@@H]3C4=C5[C@@H]([C@H](OC5=CC(=C4)O)C6=CC=C(C=C6)O)C7=C8[C@H]([C@@H](OC8=CC(=C7)O)C9=CC=C(C=C9)O)C1=C3C(=CC(=C1)O)O2)O
• InChI: InChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H/t37-,38-,39+,40+,41+,42-/m1/s1
• InChI Key: KUTVNHOAKHJJFL-ZSIJVUTGSA-N
• Popularity: 36 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₃₀O₉
• Molecular Weight: 678.70 g/mol
• Exact Mass: 678.18898253 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 8.03
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 62218-13-7
• (+)-Alpha-Viniferin
• (+)-.alpha.-Viniferin
• 53XER6FHLX
• CHEMBL443463
• CHEBI:66359
• (2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.12,5.110,13.021,25.09,27.017,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triol
• (+)--Viniferin
• Viniferin-alpha
• UNII-53XER6FHLX
• .ALPHA.-VINIFERIN
• VINIFERIN, ALPHA-
• SCHEMBL2721238
• DTXSID40211274
• HY-N2854
• BDBM50362650
• Cyclonona(1,2,3-cd:4,5,6-c'd':7,8,9-c''d'')trisbenzofuran-4,9,14-triol, 2,2a,7,7a,12,12a-hexahydro-2,7,12-tris(4-hydroxyphenyl)-, (2R*,2aR*,7R*,7aR*,12S*,12aS*)-
• CS-0023432
• 3'',4'':7,8,9]cyclonona[1,2,3-cd][1]benzofuran-4,9,14-triol
• (2R,2aR,7R,7aR,12S,12aS)-2,7,12-tris(4-hydroxyphenyl)-2,2a,7,7a,12,12a-hexahydrobis[1]benzofuro[3',4':4,5,6
• (2R,2aR,7R,7aR,12S,12aS)-2,7,12-tris(4-hydroxyphenyl)-2,2a,7,7a,12,12a-hexahydrobis[1]benzofuro[3',4':4,5,6;3'',4'':7,8,9]cyclonona[1,2,3-cd][1]benzofuran-4,9,14-triol
• CYCLONONA(1,2,3-CD:4,5,6-C'D':7,8,9-C''D'')TRISBENZOFURAN-4,9,14-TRIOL, 2,2A,7,7A,12,12A-HEXAHYDRO-2,7,12-TRIS(4-HYDROXYPHENYL)-, (2R*,2AR*,7R*,7AR*,12S*,12AS*)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	-	0.8723	87.23%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7302	73.02%
OATP2B1 inhibitior	-	0.5703	57.03%
OATP1B1 inhibitior	+	0.7465	74.65%
OATP1B3 inhibitior	+	0.9105	91.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7346	73.46%
P-glycoprotein inhibitior	+	0.7194	71.94%
P-glycoprotein substrate	-	0.9633	96.33%
CYP3A4 substrate	-	0.5905	59.05%
CYP2C9 substrate	-	0.7778	77.78%
CYP2D6 substrate	+	0.4927	49.27%
CYP3A4 inhibition	-	0.6358	63.58%
CYP2C9 inhibition	+	0.9497	94.97%
CYP2C19 inhibition	+	0.8042	80.42%
CYP2D6 inhibition	-	0.7239	72.39%
CYP1A2 inhibition	+	0.9277	92.77%
CYP2C8 inhibition	+	0.6168	61.68%
CYP inhibitory promiscuity	+	0.8617	86.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8508	85.08%
Carcinogenicity (trinary)	Warning	0.3692	36.92%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.6153	61.53%
Skin irritation	+	0.5285	52.85%
Skin corrosion	-	0.9792	97.92%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8255	82.55%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.7007	70.07%
skin sensitisation	-	0.8550	85.50%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4754	47.54%
Acute Oral Toxicity (c)	III	0.5647	56.47%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.8192	81.92%
Thyroid receptor binding	+	0.7084	70.84%
Glucocorticoid receptor binding	+	0.7043	70.43%
Aromatase binding	+	0.5186	51.86%
PPAR gamma	+	0.7843	78.43%
Honey bee toxicity	-	0.8858	88.58%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9326	93.26%

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	97.34%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.32%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.32%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	85.08%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.96%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.53%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.01%	98.95%

Plants that contains it

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

Cross-Links

• PubChem: 196402
• NPASS: NPC71686
• ChEMBL: CHEMBL443463
• LOTUS: LTS0186014
• wikiData: Q4734921