3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl)phenoxy]oxan-2-yl]methoxy]propanoic acid

Details

• Internal ID: 8b24e096-e814-4c80-a1b0-c12f9cc5af05
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl)phenoxy]oxan-2-yl]methoxy]propanoic acid
• SMILES (Canonical): C1OC2=C(O1)C=C3C(=C2)C(=O)C(=CO3)C4=CC=C(C=C4)OC5C(C(C(C(O5)COC(=O)CC(=O)O)O)O)O
• SMILES (Isomeric): C1OC2=C(O1)C=C3C(=C2)C(=O)C(=CO3)C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)CC(=O)O)O)O)O
• InChI: InChI=1S/C25H22O13/c26-19(27)7-20(28)34-9-18-22(30)23(31)24(32)25(38-18)37-12-3-1-11(2-4-12)14-8-33-15-6-17-16(35-10-36-17)5-13(15)21(14)29/h1-6,8,18,22-25,30-32H,7,9-10H2,(H,26,27)/t18-,22-,23+,24-,25-/m1/s1
• InChI Key: HAYZCQCOXWZRME-GOZZSVHWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₁₃
• Molecular Weight: 530.40 g/mol
• Exact Mass: 530.10604075 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6198	61.98%
Caco-2	-	0.9037	90.37%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6193	61.93%
OATP2B1 inhibitior	-	0.8418	84.18%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7201	72.01%
P-glycoprotein inhibitior	+	0.6649	66.49%
P-glycoprotein substrate	-	0.8106	81.06%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	-	0.8029	80.29%
CYP2D6 substrate	-	0.8656	86.56%
CYP3A4 inhibition	-	0.5154	51.54%
CYP2C9 inhibition	-	0.8863	88.63%
CYP2C19 inhibition	-	0.7872	78.72%
CYP2D6 inhibition	-	0.8682	86.82%
CYP1A2 inhibition	-	0.8907	89.07%
CYP2C8 inhibition	+	0.5460	54.60%
CYP inhibitory promiscuity	-	0.7890	78.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5636	56.36%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.8166	81.66%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5378	53.78%
Micronuclear	+	0.7559	75.59%
Hepatotoxicity	-	0.5891	58.91%
skin sensitisation	-	0.8755	87.55%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8790	87.90%
Acute Oral Toxicity (c)	III	0.5924	59.24%
Estrogen receptor binding	+	0.7954	79.54%
Androgen receptor binding	+	0.7534	75.34%
Thyroid receptor binding	-	0.5428	54.28%
Glucocorticoid receptor binding	+	0.5766	57.66%
Aromatase binding	+	0.5984	59.84%
PPAR gamma	+	0.7429	74.29%
Honey bee toxicity	-	0.8061	80.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9527	95.27%

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	99.50%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.84%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.75%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.47%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.22%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.73%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.32%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.14%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.88%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.54%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.47%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.39%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.28%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.20%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.13%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.79%	95.83%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.59%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	81.58%	94.73%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.37%	90.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.88%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.60%	94.80%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.60%	94.33%

Plants that contains it

• Trifolium pratense

Cross-Links

• PubChem: 102463145
• LOTUS: LTS0187154
• wikiData: Q105025136