5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: 31db0231-1c46-47a2-9d83-f5ab354dadb1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)O)O)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-15(32)18(35)20(37)26(39-8)43-25-17(34)14-11(30)6-12(31)23(24(14)41-22(25)9-2-4-10(29)5-3-9)42-27-21(38)19(36)16(33)13(7-28)40-27/h2-6,8,13,15-16,18-21,26-33,35-38H,7H2,1H3/t8-,13+,15-,16+,18+,19-,20+,21+,26-,27-/m0/s1
• InChI Key: ZBCIMVCVGORQFA-ZGQVXQITSA-N
• Popularity: 0 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

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	-	0.9053	90.53%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5758	57.58%
P-glycoprotein inhibitior	-	0.4887	48.87%
P-glycoprotein substrate	-	0.6385	63.85%
CYP3A4 substrate	+	0.5988	59.88%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
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	+	0.6718	67.18%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8848	88.48%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5209	52.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.6718	67.18%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.5875	58.75%
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	-	0.7756	77.56%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7594	75.94%
Androgen receptor binding	+	0.6416	64.16%
Thyroid receptor binding	-	0.4914	49.14%
Glucocorticoid receptor binding	+	0.5643	56.43%
Aromatase binding	-	0.5080	50.80%
PPAR gamma	+	0.6620	66.20%
Honey bee toxicity	-	0.7728	77.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
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	99.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.46%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.36%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.39%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.55%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.96%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.50%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	88.28%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.80%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.35%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.84%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.38%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	82.71%	98.35%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.22%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.22%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.52%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.17%	97.09%

Plants that contains it

• Ephedra aphylla

Cross-Links

• PubChem: 101714436
• LOTUS: LTS0016698
• wikiData: Q105370462