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

Details

• Internal ID: b5cb3258-ae87-461f-8251-18b1ee305cc8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)OC)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)OC)O)CO)O)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-9-18(33)21(36)23(38)27(40-9)44-26-22(37)19(34)16(8-29)42-28(26)43-25-20(35)17-13(32)6-11(30)7-15(17)41-24(25)10-3-4-14(39-2)12(31)5-10/h3-7,9,16,18-19,21-23,26-34,36-38H,8H2,1-2H3/t9-,16+,18+,19+,21+,22+,23+,26-,27+,28+/m1/s1
• InChI Key: HDBLGMREZKSBMK-QAHLOMPASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.38
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.9074	90.74%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.7096	70.96%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8508	85.08%
P-glycoprotein inhibitior	-	0.5951	59.51%
P-glycoprotein substrate	+	0.6171	61.71%
CYP3A4 substrate	+	0.6633	66.33%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.8489	84.89%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9150	91.50%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6771	67.71%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9108	91.08%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8466	84.66%
Androgen receptor binding	+	0.5547	55.47%
Thyroid receptor binding	+	0.5487	54.87%
Glucocorticoid receptor binding	+	0.6326	63.26%
Aromatase binding	+	0.5673	56.73%
PPAR gamma	+	0.7068	70.68%
Honey bee toxicity	-	0.7072	70.72%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7522	75.22%

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	98.80%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.81%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.98%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.56%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.17%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.66%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.98%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.37%	95.56%
CHEMBL3194	P02766	Transthyretin	87.61%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	87.32%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	86.90%	94.75%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.78%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.32%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.32%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.98%	97.36%
CHEMBL4208	P20618	Proteasome component C5	80.95%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.66%	99.15%

Plants that contains it

• Costus spicatus

Cross-Links

• PubChem: 162927286
• LOTUS: LTS0134966
• wikiData: Q105026248