Methyl 5-hydroxy-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-oxabicyclo[4.1.0]hepta-1,3,5-triene-3-carboxylate

Details

• Internal ID: 738a919e-dc7a-4b47-8123-6ff30eedc854
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: methyl 5-hydroxy-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-oxabicyclo[4.1.0]hepta-1,3,5-triene-3-carboxylate
• SMILES (Canonical): COC(=O)C1=CC(=C2C(=C1C3C(C(C(C(O3)CO)O)O)O)O2)O
• SMILES (Isomeric): COC(=O)C1=CC(=C2C(=C1C3C(C(C(C(O3)CO)O)O)O)O2)O
• InChI: InChI=1S/C14H16O9/c1-21-14(20)4-2-5(16)11-13(23-11)7(4)12-10(19)9(18)8(17)6(3-15)22-12/h2,6,8-10,12,15-19H,3H2,1H3
• InChI Key: DNOYEWZAPJCUNS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₉
• Molecular Weight: 328.27 g/mol
• Exact Mass: 328.07943208 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.20
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5652	56.52%
Caco-2	-	0.8756	87.56%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6072	60.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7152	71.52%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8139	81.39%
P-glycoprotein inhibitior	-	0.9087	90.87%
P-glycoprotein substrate	-	0.8776	87.76%
CYP3A4 substrate	+	0.5136	51.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.8521	85.21%
CYP2C9 inhibition	-	0.9030	90.30%
CYP2C19 inhibition	-	0.8683	86.83%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	-	0.9269	92.69%
CYP2C8 inhibition	-	0.6508	65.08%
CYP inhibitory promiscuity	-	0.8317	83.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6841	68.41%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.8884	88.84%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9493	94.93%
Ames mutagenesis	-	0.5774	57.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.5750	57.50%
Micronuclear	+	0.5533	55.33%
Hepatotoxicity	-	0.8134	81.34%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5604	56.04%
Acute Oral Toxicity (c)	III	0.6270	62.70%
Estrogen receptor binding	+	0.5454	54.54%
Androgen receptor binding	-	0.5369	53.69%
Thyroid receptor binding	-	0.5586	55.86%
Glucocorticoid receptor binding	+	0.5518	55.18%
Aromatase binding	-	0.6637	66.37%
PPAR gamma	+	0.5353	53.53%
Honey bee toxicity	-	0.8641	86.41%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.4512	45.12%

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	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.75%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.17%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	90.57%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.85%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.17%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.89%	96.00%

Plants that contains it

• Commelina communis

Cross-Links

• PubChem: 163094845
• LOTUS: LTS0054596
• wikiData: Q104985678