2-o-beta-d-Glucopyranosyl-l-ascorbic acid

Details

• Internal ID: 16cb05ff-079a-4e6a-b6a0-a35a496574d4
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-furan-5-one
• InChI: InChI=1S/C12H18O11/c13-1-3(15)9-8(19)10(11(20)22-9)23-12-7(18)6(17)5(16)4(2-14)21-12/h3-7,9,12-19H,1-2H2/t3-,4+,5+,6-,7+,9+,12-/m0/s1
• InChI Key: MLSJBGYKDYSOAE-DNYNHWTLSA-N
• Popularity: 132 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈O₁₁
• Molecular Weight: 338.26 g/mol
• Exact Mass: 338.08491139 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -4.15
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 562043-82-7
• 2-O-|A-D-Glucopyranosyl-L-ascorbic Acid
• 2-o--d-glucopyranosyl-l-ascorbic acid
• AA-2bG
• SCHEMBL152620
• MLSJBGYKDYSOAE-DNYNHWTLSA-N
• HY-N6958
• AKOS032945219
• 2-O-b-D-Glucopyranosyl-L-ascorbic acid
• 2-o-(beta-d-glucopyranosyl)ascorbic acid
• MS-25140
• 2-O-??-D-Glucopyranosyl-L-ascorbic acid
• CS-0101448
• E87120

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7878	78.78%
Caco-2	-	0.9385	93.85%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7490	74.90%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9244	92.44%
OATP1B3 inhibitior	+	0.9587	95.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9533	95.33%
P-glycoprotein inhibitior	-	0.8928	89.28%
P-glycoprotein substrate	-	0.9517	95.17%
CYP3A4 substrate	+	0.5209	52.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.9678	96.78%
CYP2C9 inhibition	-	0.9559	95.59%
CYP2C19 inhibition	-	0.9174	91.74%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.9252	92.52%
CYP2C8 inhibition	-	0.9159	91.59%
CYP inhibitory promiscuity	-	0.9026	90.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7387	73.87%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.8261	82.61%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6022	60.22%
Micronuclear	-	0.8241	82.41%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.9076	90.76%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6892	68.92%
Acute Oral Toxicity (c)	III	0.4807	48.07%
Estrogen receptor binding	+	0.5705	57.05%
Androgen receptor binding	-	0.6392	63.92%
Thyroid receptor binding	+	0.5540	55.40%
Glucocorticoid receptor binding	-	0.5705	57.05%
Aromatase binding	-	0.4903	49.03%
PPAR gamma	+	0.5519	55.19%
Honey bee toxicity	-	0.7720	77.20%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6537	65.37%
Fish aquatic toxicity	-	0.7528	75.28%

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	95.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.20%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.82%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	86.17%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.23%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.91%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.16%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.84%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.41%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.34%	97.25%

Plants that contains it

• Lycium barbarum

Cross-Links

• PubChem: 54706833
• LOTUS: LTS0041652
• wikiData: Q105167036