5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

Details

• Internal ID: 1b544c47-2b96-4a52-888b-fe4a4b647658
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-7-[(2S,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=CC(=C4C(=C3)OC(=C(C4=O)OC)C5=CC(=C(C=C5)OC)O)O)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=CC(=C4C(=C3)OC(=C(C4=O)OC)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H34O16/c1-10-19(32)22(35)24(37)28(42-10)41-9-17-20(33)23(36)25(38)29(45-17)43-12-7-14(31)18-16(8-12)44-26(27(40-3)21(18)34)11-4-5-15(39-2)13(30)6-11/h4-8,10,17,19-20,22-25,28-33,35-38H,9H2,1-3H3/t10-,17+,19-,20+,22+,23-,24+,25+,28+,29+/m0/s1
• InChI Key: ZGHMHQGZMJLPND-GGQHDFQOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₆
• Molecular Weight: 638.60 g/mol
• Exact Mass: 638.18468499 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.08
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-
• 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8874	88.74%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.5709	57.09%
OATP1B1 inhibitior	+	0.9335	93.35%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7840	78.40%
P-glycoprotein inhibitior	-	0.7943	79.43%
P-glycoprotein substrate	+	0.7144	71.44%
CYP3A4 substrate	+	0.6079	60.79%
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	+	0.8436	84.36%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7883	78.83%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9265	92.65%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	-	0.5407	54.07%
Thyroid receptor binding	+	0.5329	53.29%
Glucocorticoid receptor binding	+	0.6135	61.35%
Aromatase binding	+	0.5504	55.04%
PPAR gamma	+	0.6906	69.06%
Honey bee toxicity	-	0.7643	76.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5749	57.49%
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	98.68%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.73%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.00%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.92%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.83%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.53%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.20%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.49%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.12%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.92%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.69%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.82%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.34%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.83%	97.09%
CHEMBL3194	P02766	Transthyretin	83.98%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.91%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.38%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.04%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.33%	94.45%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.91%	95.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.12%	95.89%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Calea lantanoides
• Chromolaena odorata
• Cibotium barometz
• Coronilla cretica
• Drosera indica
• Drummondita hassellii
• Ephedra distachya
• Flindersia xanthoxyla
• Galium mollugo
• Gardenia imperialis
• Gomesa radicans
• Grindelia scorzonerifolia
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Pinus flexilis
• Psilotum nudum
• Rydingia limbata
• Senegalia mellifera
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 5495545
• NPASS: NPC145820
• LOTUS: LTS0009772
• wikiData: Q105375190