(2S)-2-(2-methylprop-1-enyl)-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one

Details

• Internal ID: 5815c1bc-deb1-4b91-a99f-3f8be9a2b88d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S)-2-(2-methylprop-1-enyl)-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): CC(=CC1CC=C(C(=O)O1)COC2C(C(C(C(O2)CO)O)O)O)C
• SMILES (Isomeric): CC(=C[C@@H]1CC=C(C(=O)O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C
• InChI: InChI=1S/C16H24O8/c1-8(2)5-10-4-3-9(15(21)23-10)7-22-16-14(20)13(19)12(18)11(6-17)24-16/h3,5,10-14,16-20H,4,6-7H2,1-2H3/t10-,11+,12+,13-,14+,16+/m0/s1
• InChI Key: MKXVLYPJBLBGIO-RRGRKSGHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₈
• Molecular Weight: 344.36 g/mol
• Exact Mass: 344.14711772 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.99
• H-Bond Acceptor: 8
• 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	-	0.7664	76.64%
Caco-2	-	0.8484	84.84%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8761	87.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7903	79.03%
P-glycoprotein inhibitior	-	0.8334	83.34%
P-glycoprotein substrate	-	0.9337	93.37%
CYP3A4 substrate	+	0.5377	53.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.9286	92.86%
CYP2C9 inhibition	-	0.8632	86.32%
CYP2C19 inhibition	-	0.8497	84.97%
CYP2D6 inhibition	-	0.8958	89.58%
CYP1A2 inhibition	-	0.9027	90.27%
CYP2C8 inhibition	-	0.8665	86.65%
CYP inhibitory promiscuity	-	0.7970	79.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6676	66.76%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.8266	82.66%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7100	71.00%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7468	74.68%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.7038	70.38%
Acute Oral Toxicity (c)	III	0.6177	61.77%
Estrogen receptor binding	+	0.6470	64.70%
Androgen receptor binding	-	0.5336	53.36%
Thyroid receptor binding	-	0.5127	51.27%
Glucocorticoid receptor binding	-	0.5394	53.94%
Aromatase binding	-	0.5100	51.00%
PPAR gamma	+	0.5189	51.89%
Honey bee toxicity	-	0.6778	67.78%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7913	79.13%

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	96.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.82%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.34%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.69%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.94%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.02%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.55%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.91%	99.17%

Plants that contains it

• Aruncus dioicus

Cross-Links

• PubChem: 162869261
• LOTUS: LTS0253240
• wikiData: Q105166315