Vincetoxicoside A

Details

• Internal ID: 3c01a9e3-b55c-49f7-bc38-836a38465f38
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1
• InChI Key: OTUCXMIQUNROBJ-JFNZIVIESA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 18016-58-5
• Quercetin 3-O-glucoside-7-O-rhamnoside
• PETIOLAROSIDE
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• Quercetin 3-glucoside 7-rhamnoside
• Quercetin 3-O-glucoside 7-O-rhamnoside
• CHEBI:67931
• DTXSID10936841
• AKOS040760660
• Quercetin3-O-glucoside-7-O-rhamnoside
• Quercetin-3-O-b-glucosyl-7-O-a-rhamnoside
• Q23418292
• quercetin-3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside
• 7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one
• 7-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9186	91.86%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5581	55.81%
OATP1B1 inhibitior	+	0.9393	93.93%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7484	74.84%
P-glycoprotein inhibitior	-	0.5565	55.65%
P-glycoprotein substrate	-	0.6370	63.70%
CYP3A4 substrate	+	0.6276	62.76%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.7955	79.55%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8889	88.89%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5399	53.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7766	77.66%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8934	89.34%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7513	75.13%
Androgen receptor binding	+	0.5879	58.79%
Thyroid receptor binding	-	0.5431	54.31%
Glucocorticoid receptor binding	+	0.5757	57.57%
Aromatase binding	-	0.5066	50.66%
PPAR gamma	+	0.6958	69.58%
Honey bee toxicity	-	0.7447	74.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.56%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.22%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.02%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.41%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.35%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.27%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.88%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.42%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.39%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.00%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.26%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.88%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.21%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.35%	95.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.83%	97.36%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.08%	95.64%
CHEMBL4208	P20618	Proteasome component C5	80.51%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.22%	90.71%

Plants that contains it

• Androsace umbellata
• Arabidopsis thaliana
• Asplenium viride
• Barbarea vulgaris
• Capsicum annuum
• Chrozophora plicata
• Delphinium staphisagria
• Elaeodendron xylocarpum
• Hippophae rhamnoides
• Lathyrus chrysanthus
• Ligustrum vulgare
• Potentilla erecta
• Pyracantha coccinea
• Sinocrassula indica
• Sorbus aria
• Vicia sativa

Cross-Links

• PubChem: 25080064
• NPASS: NPC180955
• LOTUS: LTS0148951
• wikiData: Q23418292