5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside

Details

• Internal ID: b0d9584c-cbe9-40ce-aded-6f7dc364a656
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)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(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-8,10,19,21-31,33-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChI Key: VCCNKWWXYVWTLT-CYZBKYQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 38665-01-9
• 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• Diosmetin-7-O-neohesperidoside
• ergotaminetartrate
• SCHEMBL7027037
• DTXSID80741565
• EX-A5254
• HY-N4122
• s9322
• AKOS040750431
• CCG-270215
• CS-T-59214
• BS-49445
• CS-0032135
• N1161
• Q63395368
• 7-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8927	89.27%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5763	57.63%
OATP1B1 inhibitior	+	0.9449	94.49%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6070	60.70%
P-glycoprotein inhibitior	-	0.7629	76.29%
P-glycoprotein substrate	+	0.7088	70.88%
CYP3A4 substrate	+	0.6063	60.63%
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	+	0.7488	74.88%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7247	72.47%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9173	91.73%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8317	83.17%
Androgen receptor binding	-	0.5261	52.61%
Thyroid receptor binding	+	0.5638	56.38%
Glucocorticoid receptor binding	+	0.5913	59.13%
Aromatase binding	+	0.5743	57.43%
PPAR gamma	+	0.7399	73.99%
Honey bee toxicity	-	0.6477	64.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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	99.04%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.71%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.99%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.68%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.18%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.10%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.46%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.29%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.52%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.51%	96.09%
CHEMBL3194	P02766	Transthyretin	90.26%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.28%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.84%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.76%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.25%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.42%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.46%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.74%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.47%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.43%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.23%	95.89%

Plants that contains it

• Citrus × aurantium
• Citrus maxima
• Trollius ledebourii

Cross-Links

• PubChem: 69964214
• NPASS: NPC81945
• LOTUS: LTS0083315
• wikiData: Q63395368