3,4,5-Trihydroxy-6-(8-hydroxy-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid

Details

• Internal ID: e8ddabb2-306e-46cd-b8c8-f22010b4c2a8
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 3,4,5-trihydroxy-6-(8-hydroxy-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C2=C1C=CC(=O)O2)O)OC3C(C(C(C(O3)C(=O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C2=C1C=CC(=O)O2)O)OC3C(C(C(C(O3)C(=O)O)O)O)O
• InChI: InChI=1S/C15H14O10/c16-7-4-2-5-1-3-6(8(17)12(5)24-7)23-15-11(20)9(18)10(19)13(25-15)14(21)22/h1-4,9-11,13,15,17-20H,(H,21,22)
• InChI Key: WDNFFLGXIZETEG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₁₀
• Molecular Weight: 354.26 g/mol
• Exact Mass: 354.05869664 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 3,4,5-trihydroxy-6-(8-hydroxy-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid
• 3,4,5-trihydroxy-6-[(8-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6378	63.78%
Caco-2	-	0.9523	95.23%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5663	56.63%
OATP2B1 inhibitior	-	0.5312	53.12%
OATP1B1 inhibitior	+	0.9314	93.14%
OATP1B3 inhibitior	+	0.9628	96.28%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9232	92.32%
P-glycoprotein inhibitior	-	0.9114	91.14%
P-glycoprotein substrate	-	0.9569	95.69%
CYP3A4 substrate	-	0.5415	54.15%
CYP2C9 substrate	-	0.8139	81.39%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.7876	78.76%
CYP2C9 inhibition	-	0.8720	87.20%
CYP2C19 inhibition	-	0.8408	84.08%
CYP2D6 inhibition	-	0.9560	95.60%
CYP1A2 inhibition	-	0.6884	68.84%
CYP2C8 inhibition	+	0.6469	64.69%
CYP inhibitory promiscuity	-	0.8826	88.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6916	69.16%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.6713	67.13%
Skin irritation	-	0.5810	58.10%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8315	83.15%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8226	82.26%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7933	79.33%
Acute Oral Toxicity (c)	III	0.3808	38.08%
Estrogen receptor binding	+	0.5614	56.14%
Androgen receptor binding	+	0.5644	56.44%
Thyroid receptor binding	-	0.6008	60.08%
Glucocorticoid receptor binding	+	0.5689	56.89%
Aromatase binding	+	0.5361	53.61%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9052	90.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9484	94.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	95.91%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.75%	91.11%
CHEMBL3194	P02766	Transthyretin	90.40%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.15%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.77%	83.57%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.33%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.88%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.52%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.21%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.86%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.44%	86.33%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 75082028
• LOTUS: LTS0166480
• wikiData: Q105302549