3-[[(3aR,5R,6S,7S,7aR)-6,7-dihydroxy-3-(2-hydroxyphenyl)-2-oxo-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d][1,3]oxazol-5-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: 438110ed-1ef8-4b9e-a143-d20b0c9c6e85
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-4-unsubstituted benzenoids
• IUPAC Name: 3-[[(3aR,5R,6S,7S,7aR)-6,7-dihydroxy-3-(2-hydroxyphenyl)-2-oxo-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d][1,3]oxazol-5-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): C1=CC=C(C(=C1)N2C3C(C(C(C(O3)COC(=O)CC(=O)O)O)O)OC2=O)O
• SMILES (Isomeric): C1=CC=C(C(=C1)N2[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)CC(=O)O)O)O)OC2=O)O
• InChI: InChI=1S/C16H17NO10/c18-8-4-2-1-3-7(8)17-15-14(27-16(17)24)13(23)12(22)9(26-15)6-25-11(21)5-10(19)20/h1-4,9,12-15,18,22-23H,5-6H2,(H,19,20)/t9-,12-,13+,14-,15-/m1/s1
• InChI Key: UBNYULGLIGRDSX-SWMGHYKJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇NO₁₀
• Molecular Weight: 383.31 g/mol
• Exact Mass: 383.08524574 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.82
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7408	74.08%
Caco-2	-	0.7807	78.07%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5098	50.98%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.8897	88.97%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9110	91.10%
BSEP inhibitior	-	0.6340	63.40%
P-glycoprotein inhibitior	-	0.7807	78.07%
P-glycoprotein substrate	-	0.8807	88.07%
CYP3A4 substrate	+	0.5341	53.41%
CYP2C9 substrate	-	0.8030	80.30%
CYP2D6 substrate	-	0.8125	81.25%
CYP3A4 inhibition	-	0.8979	89.79%
CYP2C9 inhibition	-	0.8589	85.89%
CYP2C19 inhibition	-	0.8492	84.92%
CYP2D6 inhibition	-	0.8393	83.93%
CYP1A2 inhibition	-	0.7932	79.32%
CYP2C8 inhibition	-	0.7226	72.26%
CYP inhibitory promiscuity	-	0.9525	95.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4956	49.56%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.7858	78.58%
Skin irritation	-	0.7988	79.88%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6892	68.92%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5888	58.88%
skin sensitisation	-	0.8809	88.09%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7166	71.66%
Acute Oral Toxicity (c)	III	0.6741	67.41%
Estrogen receptor binding	+	0.7010	70.10%
Androgen receptor binding	-	0.6962	69.62%
Thyroid receptor binding	-	0.6805	68.05%
Glucocorticoid receptor binding	-	0.5234	52.34%
Aromatase binding	-	0.5554	55.54%
PPAR gamma	+	0.5531	55.31%
Honey bee toxicity	-	0.9198	91.98%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9392	93.92%

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	97.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.06%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	91.19%	83.82%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.27%	95.64%
CHEMBL221	P23219	Cyclooxygenase-1	88.95%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.69%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.88%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.09%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%

Plants that contains it

• Zea mays

Cross-Links

• PubChem: 11617890
• LOTUS: LTS0266063
• wikiData: Q105269517