3-[7-[(2R,3R,4S,5S,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methyloxan-2-yl]oxy-3-(4-methoxyphenyl)-4-oxochromen-2-yl]oxy-3-oxopropanoic acid

Details

• Internal ID: b44701eb-6873-4202-b869-023de20c1650
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-[7-[(2R,3R,4S,5S,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-methyloxan-2-yl]oxy-3-(4-methoxyphenyl)-4-oxochromen-2-yl]oxy-3-oxopropanoic acid
• SMILES (Canonical): CC1C(OC(C(C1O)O)OC2=CC3=C(C=C2)C(=O)C(=C(O3)OC(=O)CC(=O)O)C4=CC=C(C=C4)OC)CO
• SMILES (Isomeric): C[C@@H]1[C@H](O[C@@H]([C@@H]([C@H]1O)O)OC2=CC3=C(C=C2)C(=O)C(=C(O3)OC(=O)CC(=O)O)C4=CC=C(C=C4)OC)CO
• InChI: InChI=1S/C26H26O12/c1-12-18(11-27)37-26(24(33)22(12)31)35-15-7-8-16-17(9-15)36-25(38-20(30)10-19(28)29)21(23(16)32)13-3-5-14(34-2)6-4-13/h3-9,12,18,22,24,26-27,31,33H,10-11H2,1-2H3,(H,28,29)/t12-,18-,22+,24-,26+/m1/s1
• InChI Key: DVTYHDJISDVAAM-PIGBDQBESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆O₁₂
• Molecular Weight: 530.50 g/mol
• Exact Mass: 530.14242626 g/mol
• Topological Polar Surface Area (TPSA): 178.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7762	77.62%
Caco-2	-	0.8668	86.68%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6561	65.61%
OATP2B1 inhibitior	-	0.8440	84.40%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9047	90.47%
P-glycoprotein inhibitior	+	0.6409	64.09%
P-glycoprotein substrate	-	0.5273	52.73%
CYP3A4 substrate	+	0.6493	64.93%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.9042	90.42%
CYP2C9 inhibition	-	0.8871	88.71%
CYP2C19 inhibition	-	0.9401	94.01%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.5712	57.12%
CYP inhibitory promiscuity	-	0.9037	90.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7316	73.16%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.8285	82.85%
Skin corrosion	-	0.9569	95.69%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6595	65.95%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8668	86.68%
Acute Oral Toxicity (c)	III	0.6891	68.91%
Estrogen receptor binding	+	0.7563	75.63%
Androgen receptor binding	+	0.7329	73.29%
Thyroid receptor binding	-	0.5482	54.82%
Glucocorticoid receptor binding	+	0.6145	61.45%
Aromatase binding	-	0.5853	58.53%
PPAR gamma	+	0.6847	68.47%
Honey bee toxicity	-	0.8043	80.43%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.8659	86.59%

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	99.34%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.83%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	96.34%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	96.12%	86.92%
CHEMBL2581	P07339	Cathepsin D	95.67%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.38%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.86%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.99%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.88%	94.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	90.58%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.14%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.66%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.45%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.02%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.65%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.64%	81.11%
CHEMBL340	P08684	Cytochrome P450 3A4	82.34%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.20%	94.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.01%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.29%	97.09%

Plants that contains it

• Cicer arietinum
• Verbascum phlomoides
• Verbascum sinuatum

Cross-Links

• PubChem: 162879552
• LOTUS: LTS0266731
• wikiData: Q104997618