5,7-Dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbutyl)-4-oxo-4H-chromen-3-YL 6-deoxy-alpha-L-mannopyranoside

Details

• Internal ID: 38c2f8a2-5add-4c09-9581-4c8a1102e6cc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbutyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CCC(C)C)C4=CC=C(C=C4)OC)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CCC(C)C)C4=CC=C(C=C4)OC)O)O)O
• InChI: InChI=1S/C27H32O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h6-9,11-13,20,22-23,27-30,32-33H,5,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
• InChI Key: PFVZUXQCELCLBL-LVKFHIPRSA-N
• Popularity: 169 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₀
• Molecular Weight: 516.50 g/mol
• Exact Mass: 516.19954721 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 7CA
• BDBM15338
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbutyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• Q27456703
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbutyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chromen-4-one
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbutyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7300	73.00%
Caco-2	-	0.8632	86.32%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6949	69.49%
OATP2B1 inhibitior	-	0.7077	70.77%
OATP1B1 inhibitior	+	0.8883	88.83%
OATP1B3 inhibitior	+	0.8560	85.60%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5894	58.94%
P-glycoprotein inhibitior	+	0.6890	68.90%
P-glycoprotein substrate	+	0.5564	55.64%
CYP3A4 substrate	+	0.6444	64.44%
CYP2C9 substrate	-	0.6855	68.55%
CYP2D6 substrate	-	0.8412	84.12%
CYP3A4 inhibition	-	0.8889	88.89%
CYP2C9 inhibition	-	0.7085	70.85%
CYP2C19 inhibition	-	0.7911	79.11%
CYP2D6 inhibition	-	0.8510	85.10%
CYP1A2 inhibition	-	0.6582	65.82%
CYP2C8 inhibition	+	0.5713	57.13%
CYP inhibitory promiscuity	-	0.7256	72.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6837	68.37%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.7765	77.65%
Skin corrosion	-	0.9316	93.16%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4764	47.64%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9020	90.20%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9001	90.01%
Acute Oral Toxicity (c)	III	0.5817	58.17%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7505	75.05%
Thyroid receptor binding	+	0.5147	51.47%
Glucocorticoid receptor binding	+	0.7736	77.36%
Aromatase binding	+	0.6255	62.55%
PPAR gamma	+	0.6006	60.06%
Honey bee toxicity	-	0.8055	80.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9789	97.89%

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	99.68%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.81%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.71%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.10%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.80%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.68%	85.14%
CHEMBL1907	P15144	Aminopeptidase N	93.79%	93.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.05%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.13%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.18%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.02%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.87%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.83%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.23%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.48%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.40%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.71%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.26%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	84.21%	91.49%
CHEMBL4208	P20618	Proteasome component C5	84.00%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.53%	92.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.22%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%

Plants that contains it

• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense

Cross-Links

• PubChem: 6852214
• NPASS: NPC76648
• LOTUS: LTS0080692
• wikiData: Q27456703