6,7,8-Trihydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

Details

• Internal ID: bbdc035c-dc82-4b8a-b3ca-a6f60ada70f4
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 6,7,8-trihydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): C1=CC(=O)OC2=C1C(=C(C(=C2O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CC(=O)OC2=C1C(=C(C(=C2O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C15H16O11/c16-3-5-7(18)8(19)12(23)15(24-5)26-14-4-1-2-6(17)25-13(4)10(21)9(20)11(14)22/h1-2,5,7-8,12,15-16,18-23H,3H2
• InChI Key: WVEUSXRGMPMCGM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₁₁
• Molecular Weight: 372.28 g/mol
• Exact Mass: 372.06926132 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5923	59.23%
Caco-2	-	0.9110	91.10%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5362	53.62%
OATP2B1 inhibitior	-	0.5479	54.79%
OATP1B1 inhibitior	+	0.8651	86.51%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8955	89.55%
P-glycoprotein inhibitior	-	0.8970	89.70%
P-glycoprotein substrate	-	0.8907	89.07%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.9207	92.07%
CYP2C9 inhibition	-	0.9414	94.14%
CYP2C19 inhibition	-	0.9119	91.19%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6982	69.82%
CYP inhibitory promiscuity	-	0.8472	84.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7090	70.90%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7251	72.51%
Skin irritation	-	0.7983	79.83%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5581	55.81%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.5446	54.46%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8488	84.88%
Acute Oral Toxicity (c)	III	0.4513	45.13%
Estrogen receptor binding	+	0.5856	58.56%
Androgen receptor binding	+	0.5834	58.34%
Thyroid receptor binding	-	0.5945	59.45%
Glucocorticoid receptor binding	+	0.6527	65.27%
Aromatase binding	+	0.5589	55.89%
PPAR gamma	+	0.6428	64.28%
Honey bee toxicity	-	0.7991	79.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	+	0.7790	77.90%

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	99.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	92.94%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.18%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.28%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.86%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.67%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.29%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.79%	99.23%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.55%	96.37%

Plants that contains it

• Tetraphis pellucida

Cross-Links

• PubChem: 163038519
• LOTUS: LTS0029406
• wikiData: Q105313496