5-hydroxy-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Details

• Internal ID: 7e7f58a6-f781-4df5-a82d-6d6707d88dda
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)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=C(OC3=CC(=CC(=C3C2=O)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/C27H30O17/c1-7-16(32)20(36)22(38)26(40-7)44-25-19(35)15-10(29)4-9(41-27-23(39)21(37)18(34)14(6-28)43-27)5-13(15)42-24(25)8-2-11(30)17(33)12(31)3-8/h2-5,7,14,16,18,20-23,26-34,36-39H,6H2,1H3/t7-,14-,16-,18+,20+,21-,22-,23+,26-,27+/m0/s1
• InChI Key: GCVLSSMQGXPXDX-LIRIZSJSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₇
• Molecular Weight: 626.50 g/mol
• Exact Mass: 626.14829948 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.33
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9102	91.02%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4760	47.60%
P-glycoprotein inhibitior	-	0.5535	55.35%
P-glycoprotein substrate	-	0.5932	59.32%
CYP3A4 substrate	+	0.6130	61.30%
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	+	0.6951	69.51%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8922	89.22%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5299	52.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7267	72.67%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9015	90.15%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7183	71.83%
Androgen receptor binding	+	0.5644	56.44%
Thyroid receptor binding	+	0.5363	53.63%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5373	53.73%
PPAR gamma	+	0.6794	67.94%
Honey bee toxicity	-	0.7890	78.90%
Biodegradation	-	0.8000	80.00%
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	99.74%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.24%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.11%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.33%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.16%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.90%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.36%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.53%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.09%	95.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.11%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.47%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.45%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.52%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.35%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL3194	P02766	Transthyretin	81.98%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.84%	86.92%

Plants that contains it

• Lithophragma bolanderi

Cross-Links

• PubChem: 163067513
• LOTUS: LTS0160136
• wikiData: Q105006499