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

Details

• Internal ID: a97a7377-7285-4b4d-8e4e-ba1060ff13f5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-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=C(C(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)C5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-8-19(32)22(35)25(38)27(39-8)42-15-6-14-17(12(31)5-13(40-14)9-2-3-10(29)11(30)4-9)21(34)18(15)26-24(37)23(36)20(33)16(7-28)41-26/h2-6,8,16,19-20,22-30,32-38H,7H2,1H3/t8-,16+,19-,20+,22+,23-,24+,25+,26?,27-/m0/s1
• InChI Key: BWFNSKPHIOFUMZ-WHGHPVCESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.70
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 5

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	-	0.9183	91.83%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5622	56.22%
OATP1B1 inhibitior	+	0.8356	83.56%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6816	68.16%
P-glycoprotein inhibitior	-	0.6463	64.63%
P-glycoprotein substrate	-	0.5212	52.12%
CYP3A4 substrate	+	0.6150	61.50%
CYP2C9 substrate	-	0.6724	67.24%
CYP2D6 substrate	-	0.8609	86.09%
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	+	0.7495	74.95%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5635	56.35%
Human Ether-a-go-go-Related Gene inhibition	+	0.7084	70.84%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9300	93.00%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7471	74.71%
Androgen receptor binding	+	0.6553	65.53%
Thyroid receptor binding	+	0.5417	54.17%
Glucocorticoid receptor binding	+	0.5684	56.84%
Aromatase binding	+	0.5393	53.93%
PPAR gamma	+	0.7135	71.35%
Honey bee toxicity	-	0.7077	70.77%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6249	62.49%
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	99.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.85%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.54%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.37%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.79%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.00%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.63%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.55%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.07%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	90.84%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.86%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.29%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.80%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.40%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.35%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	83.68%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.65%	97.09%

Plants that contains it

• Hyparrhenia hirta

Cross-Links

• PubChem: 162834054
• LOTUS: LTS0048608
• wikiData: Q104947205