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

Details

• Internal ID: 270c529e-cefd-49f8-83c6-fc1c99c2793a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C26H28O14/c27-7-15-19(33)21(35)25(40-26-22(36)20(34)16(8-28)39-26)24(38-15)18-12(31)5-11(30)17-13(32)6-14(37-23(17)18)9-1-3-10(29)4-2-9/h1-6,15-16,19-22,24-31,33-36H,7-8H2/t15-,16-,19-,20+,21+,22-,24+,25-,26+/m1/s1
• InChI Key: BBUDILRMCLBZGM-UXMIUJOESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.44
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5737	57.37%
Caco-2	-	0.9323	93.23%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6767	67.67%
OATP2B1 inhibitior	-	0.5523	55.23%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7607	76.07%
P-glycoprotein inhibitior	-	0.6196	61.96%
P-glycoprotein substrate	-	0.7854	78.54%
CYP3A4 substrate	+	0.6167	61.67%
CYP2C9 substrate	-	0.6643	66.43%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.8613	86.13%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.8109	81.09%
CYP2D6 inhibition	-	0.9082	90.82%
CYP1A2 inhibition	-	0.8791	87.91%
CYP2C8 inhibition	+	0.6614	66.14%
CYP inhibitory promiscuity	-	0.5669	56.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.8230	82.30%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5536	55.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4395	43.95%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7913	79.13%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7195	71.95%
Acute Oral Toxicity (c)	III	0.5291	52.91%
Estrogen receptor binding	+	0.8046	80.46%
Androgen receptor binding	+	0.7782	77.82%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	+	0.5459	54.59%
Aromatase binding	+	0.7178	71.78%
PPAR gamma	+	0.7365	73.65%
Honey bee toxicity	-	0.6831	68.31%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8457	84.57%

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	99.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.68%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.70%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.84%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.80%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.38%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.33%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.24%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.42%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.75%	96.21%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.59%	83.57%
CHEMBL3194	P02766	Transthyretin	84.83%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.44%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	83.42%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.65%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.25%	91.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.24%	89.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.34%	94.45%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.09%	91.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.86%	95.83%

Plants that contains it

• Passiflora serratodigitata

Cross-Links

• PubChem: 162897225
• LOTUS: LTS0037345
• wikiData: Q104923067