3-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl]oxy-2,2-dimethyl-3-oxopropanoic acid

Details

• Internal ID: 224665de-0afc-4d2e-a67e-429ff758b6b2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Sugar acids and derivatives
• IUPAC Name: 3-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl]oxy-2,2-dimethyl-3-oxopropanoic acid
• SMILES (Canonical): CC(C)(C(=O)O)C(=O)OC1C(OC(C(C1O)O)OCC2=CC=CC=C2)CO
• SMILES (Isomeric): CC(C)(C(=O)O)C(=O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)OCC2=CC=CC=C2)CO
• InChI: InChI=1S/C18H24O9/c1-18(2,16(22)23)17(24)27-14-11(8-19)26-15(13(21)12(14)20)25-9-10-6-4-3-5-7-10/h3-7,11-15,19-21H,8-9H2,1-2H3,(H,22,23)/t11-,12-,13-,14-,15-/m1/s1
• InChI Key: VGZDULIFBZHTGM-KJWHEZOQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₉
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.14203234 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 8
• 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	-	0.6682	66.82%
Caco-2	-	0.7826	78.26%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8831	88.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8847	88.47%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6259	62.59%
P-glycoprotein inhibitior	-	0.6559	65.59%
P-glycoprotein substrate	-	0.9269	92.69%
CYP3A4 substrate	+	0.5369	53.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8850	88.50%
CYP3A4 inhibition	-	0.9132	91.32%
CYP2C9 inhibition	-	0.7633	76.33%
CYP2C19 inhibition	-	0.8641	86.41%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.9054	90.54%
CYP2C8 inhibition	-	0.6177	61.77%
CYP inhibitory promiscuity	-	0.8546	85.46%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6693	66.93%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9302	93.02%
Skin irritation	-	0.8798	87.98%
Skin corrosion	-	0.9569	95.69%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6445	64.45%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	-	0.7018	70.18%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.5963	59.63%
Acute Oral Toxicity (c)	III	0.6457	64.57%
Estrogen receptor binding	+	0.6910	69.10%
Androgen receptor binding	-	0.5273	52.73%
Thyroid receptor binding	+	0.5246	52.46%
Glucocorticoid receptor binding	+	0.5911	59.11%
Aromatase binding	-	0.6499	64.99%
PPAR gamma	+	0.6226	62.26%
Honey bee toxicity	-	0.8429	84.29%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6784	67.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.52%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.07%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.67%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.65%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.78%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.49%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.31%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.84%	95.50%

Plants that contains it

• Carica papaya

Cross-Links

• PubChem: 163060604
• LOTUS: LTS0195219
• wikiData: Q105286241