3-Hexenyl-beta-glucopyranoside

Details

• Internal ID: e296b023-dfba-46f7-a6e1-09b919585348
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(E)-hex-3-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CCC=CCCOC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): CC/C=C/CCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C12H22O6/c1-2-3-4-5-6-17-12-11(16)10(15)9(14)8(7-13)18-12/h3-4,8-16H,2,5-7H2,1H3/b4-3+/t8-,9-,10+,11-,12-/m1/s1
• InChI Key: OZIPFYKAIOOVEJ-WQPBHKFLSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.14163842 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.84
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 3-Hexenyl-beta-D-glucopyranoside
• (2R,3R,4S,5S,6R)-2-[(E)-hex-3-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 95632-87-4
• Erigeside B
• CHEMBL2152486
• beta-D-Glucopyranoside, 3-hexenyl, (Z)-
• 156848-84-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8273	82.73%
Caco-2	-	0.8131	81.31%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8113	81.13%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9363	93.63%
P-glycoprotein inhibitior	-	0.9473	94.73%
P-glycoprotein substrate	-	0.9709	97.09%
CYP3A4 substrate	-	0.5248	52.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8327	83.27%
CYP3A4 inhibition	-	0.9429	94.29%
CYP2C9 inhibition	-	0.9066	90.66%
CYP2C19 inhibition	-	0.7778	77.78%
CYP2D6 inhibition	-	0.9147	91.47%
CYP1A2 inhibition	-	0.8859	88.59%
CYP2C8 inhibition	-	0.8671	86.71%
CYP inhibitory promiscuity	-	0.8809	88.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7159	71.59%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9693	96.93%
Skin irritation	-	0.8182	81.82%
Skin corrosion	-	0.9669	96.69%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5296	52.96%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.8790	87.90%
skin sensitisation	-	0.8722	87.22%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.6336	63.36%
Acute Oral Toxicity (c)	III	0.5313	53.13%
Estrogen receptor binding	-	0.8516	85.16%
Androgen receptor binding	-	0.7195	71.95%
Thyroid receptor binding	-	0.5609	56.09%
Glucocorticoid receptor binding	-	0.6190	61.90%
Aromatase binding	-	0.7724	77.24%
PPAR gamma	+	0.5305	53.05%
Honey bee toxicity	-	0.8656	86.56%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	-	0.4692	46.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.64%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.84%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.26%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	86.23%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.32%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	84.13%	94.73%
CHEMBL2581	P07339	Cathepsin D	82.39%	98.95%
CHEMBL3589	P55263	Adenosine kinase	80.74%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.31%	97.09%

Plants that contains it

• Cinnamomum subavenium
• Erigeron breviscapus
• Ziziphora clinopodioides

Cross-Links

• PubChem: 5318046
• NPASS: NPC294813
• LOTUS: LTS0227512
• wikiData: Q105203849