5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxymethyl]-2-oxanyl]oxy]-1-benzopyran-4-one

Details

• Internal ID: 87d85ec6-9b4c-4f16-a208-80464f42465e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)OC)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)OC)O)O)O)O)O)O
• InChI: InChI=1S/C29H34O15/c1-11-20(31)23(34)25(36)28(41-11)40-10-18-21(32)24(35)26(37)29(44-18)43-17-9-16-19(22(33)27(17)39-3)14(30)8-15(42-16)12-4-6-13(38-2)7-5-12/h4-9,11,18,20-21,23-26,28-29,31-37H,10H2,1-3H3/t11-,18+,20-,21+,23+,24-,25+,26+,28+,29-/m0/s1
• InChI Key: DUXQKCCELUKXOE-NCNDPSPSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₅
• Molecular Weight: 622.60 g/mol
• Exact Mass: 622.18977037 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.79
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-
• 5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxymethyl]-2-oxanyl]oxy]-1-benzopyran-4-one
• C29H34O15
• C29-H34-O15
• Spectrum_000529
• SpecPlus_000298
• Spectrum2_000210
• Spectrum3_000166
• Spectrum4_001489
• Spectrum5_000197
• BSPBio_001631
• KBioGR_002097
• KBioSS_001009
• SPECTRUM200115
• DivK1c_006394
• SPBio_000199
• SCHEMBL22680317
• KBio1_001338
• KBio2_001009
• KBio2_003577
• KBio2_006145
• KBio3_001131
• CHEBI:109534
• CCG-38413
• AKOS015909680
• SDCCGMLS-0066414.P001
• NCGC00179136-01
• SR-05000002766
• SR-05000002766-1
• BRD-K20043699-001-02-3
• BRD-K20043699-001-03-1
• Q27188681

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8758	87.58%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.5742	57.42%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8031	80.31%
P-glycoprotein inhibitior	-	0.6881	68.81%
P-glycoprotein substrate	+	0.6242	62.42%
CYP3A4 substrate	+	0.6204	62.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9351	93.51%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	+	0.6967	69.67%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9294	92.94%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.6164	61.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7304	73.04%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9665	96.65%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.8101	81.01%
Androgen receptor binding	+	0.6088	60.88%
Thyroid receptor binding	+	0.5388	53.88%
Glucocorticoid receptor binding	+	0.6481	64.81%
Aromatase binding	+	0.5445	54.45%
PPAR gamma	+	0.6931	69.31%
Honey bee toxicity	-	0.7900	79.00%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.8533	85.33%

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	99.71%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.13%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.10%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.31%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.96%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.12%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.73%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.22%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.94%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.55%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.46%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.03%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.94%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	85.77%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.02%	97.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.80%	81.11%
CHEMBL1907	P15144	Aminopeptidase N	82.80%	93.31%
CHEMBL4208	P20618	Proteasome component C5	81.83%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.69%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.29%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.16%	97.36%

Plants that contains it

• Cirsium arvense
• Cirsium japonicum
• Duranta erecta
• Potentilla chinensis
• Trifolium pratense

Cross-Links

• PubChem: 6708644
• NPASS: NPC157663