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

Details

• Internal ID: a9969a12-d12f-4068-8b00-d930811d47b3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=CC4=C3C(=O)C=C(O4)C5=CC(=C(C=C5)O)O)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=CC(=CC4=C3C(=O)C=C(O4)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)40-17-6-11(29)5-16-19(17)14(32)7-15(39-16)10-2-3-12(30)13(31)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m1/s1
• InChI Key: BPDCNECYBTUJGT-JNJMNIGZSA-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): 245.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• 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	-	0.4777	47.77%
Caco-2	-	0.9206	92.06%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5663	56.63%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6078	60.78%
P-glycoprotein inhibitior	-	0.7450	74.50%
P-glycoprotein substrate	-	0.5205	52.05%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
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	+	0.7254	72.54%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3890	38.90%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7875	78.75%
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	-	0.8626	86.26%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8074	80.74%
Androgen receptor binding	+	0.6123	61.23%
Thyroid receptor binding	+	0.5885	58.85%
Glucocorticoid receptor binding	+	0.6011	60.11%
Aromatase binding	+	0.6304	63.04%
PPAR gamma	+	0.7704	77.04%
Honey bee toxicity	-	0.6454	64.54%
Biodegradation	-	0.8250	82.50%
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	99.59%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.16%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.56%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.73%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.94%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.93%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.54%	97.36%
CHEMBL3194	P02766	Transthyretin	91.56%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.98%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.90%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.64%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.79%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.36%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.81%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.30%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.20%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.03%	85.14%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.42%	80.78%

Plants that contains it

• Carallia brachiata

Cross-Links

• PubChem: 162932223
• LOTUS: LTS0025373
• wikiData: Q104941784