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

Details

• Internal ID: a2808bdb-cb62-4110-95cc-e450c50506d5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)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)O)O)O)C)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)O)O)O)C)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-7-16(32)20(36)22(38)26(39-7)43-25-21(37)17(33)8(2)40-27(25)42-24-19(35)15-11(29)5-10(28)6-14(15)41-23(24)9-3-12(30)18(34)13(31)4-9/h3-8,16-17,20-22,25-34,36-38H,1-2H3/t7-,8-,16-,17-,20+,21+,22+,25+,26-,27-/m0/s1
• InChI Key: UMLQYKKIQCBBDM-XYSSDXFWSA-N
• Popularity: 2 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: -0.60
• Atomic LogP (AlogP): -0.95
• H-Bond Acceptor: 16
• 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	+	0.8072	80.72%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7235	72.35%
OATP2B1 inhibitior	-	0.5596	55.96%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.8556	85.56%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7443	74.43%
P-glycoprotein inhibitior	-	0.5456	54.56%
P-glycoprotein substrate	-	0.5168	51.68%
CYP3A4 substrate	+	0.6422	64.22%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.6813	68.13%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.8648	86.48%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.6999	69.99%
CYP2C8 inhibition	+	0.7853	78.53%
CYP inhibitory promiscuity	-	0.5626	56.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6369	63.69%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8912	89.12%
Skin irritation	-	0.6827	68.27%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5514	55.14%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5697	56.97%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8743	87.43%
Acute Oral Toxicity (c)	III	0.4830	48.30%
Estrogen receptor binding	+	0.8141	81.41%
Androgen receptor binding	+	0.6625	66.25%
Thyroid receptor binding	+	0.6272	62.72%
Glucocorticoid receptor binding	+	0.6736	67.36%
Aromatase binding	+	0.5258	52.58%
PPAR gamma	+	0.7477	74.77%
Honey bee toxicity	-	0.7772	77.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5350	53.50%
Fish aquatic toxicity	+	0.9566	95.66%

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	99.65%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.60%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.26%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.64%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.00%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.39%	97.36%
CHEMBL2581	P07339	Cathepsin D	94.31%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.32%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL3194	P02766	Transthyretin	89.84%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.54%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.23%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.22%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.19%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.40%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.84%	91.38%
CHEMBL4208	P20618	Proteasome component C5	82.46%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.57%	96.09%
CHEMBL4530	P00488	Coagulation factor XIII	80.51%	96.00%

Plants that contains it

• Alyxia reinwardtii
• Centaurea linifolia
• Cneoridium dumosum
• Leuzea centauroides
• Licania densiflora
• Limonium gmelinii
• Machilus glaucescens
• Microtropis fokienensis
• Thymus vulgaris
• Vitellaria paradoxa

Cross-Links

• PubChem: 101036025
• NPASS: NPC231644
• LOTUS: LTS0221630
• wikiData: Q105275614