(1S,7abeta)-Hexahydro-2alpha-[(beta-D-glucopyranosyl)oxy]-3beta-(hydroxymethyl)-1H-pyrrolizine-1alpha,7alpha-diol

Details

• Internal ID: 32bdb825-31e6-4a11-a858-c20d466cf680
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,2R,3R,7S,8R)-1,7-dihydroxy-3-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1CN2C(C(C(C2C1O)O)OC3C(C(C(C(O3)CO)O)O)O)CO
• SMILES (Isomeric): C1CN2[C@@H]([C@H]([C@H]([C@H]2[C@H]1O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
• InChI: InChI=1S/C14H25NO9/c16-3-5-13(10(20)8-6(18)1-2-15(5)8)24-14-12(22)11(21)9(19)7(4-17)23-14/h5-14,16-22H,1-4H2/t5-,6+,7-,8-,9-,10+,11+,12-,13-,14+/m1/s1
• InChI Key: OJXPOESQKZPFOR-NCLRVDEFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₅NO₉
• Molecular Weight: 351.35 g/mol
• Exact Mass: 351.15293138 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -4.66
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6450	64.50%
Caco-2	-	0.8669	86.69%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Lysosomes	0.4776	47.76%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9159	91.59%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9342	93.42%
P-glycoprotein inhibitior	-	0.9204	92.04%
P-glycoprotein substrate	-	0.9244	92.44%
CYP3A4 substrate	+	0.5281	52.81%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.7005	70.05%
CYP3A4 inhibition	-	0.9964	99.64%
CYP2C9 inhibition	-	0.9439	94.39%
CYP2C19 inhibition	-	0.9333	93.33%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.8401	84.01%
CYP2C8 inhibition	-	0.9124	91.24%
CYP inhibitory promiscuity	-	0.9744	97.44%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6199	61.99%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.9648	96.48%
Skin irritation	-	0.7647	76.47%
Skin corrosion	-	0.9248	92.48%
Ames mutagenesis	-	0.8070	80.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4215	42.15%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.8575	85.75%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6470	64.70%
Acute Oral Toxicity (c)	III	0.5051	50.51%
Estrogen receptor binding	-	0.8227	82.27%
Androgen receptor binding	-	0.5922	59.22%
Thyroid receptor binding	+	0.6282	62.82%
Glucocorticoid receptor binding	-	0.7904	79.04%
Aromatase binding	+	0.5577	55.77%
PPAR gamma	+	0.5748	57.48%
Honey bee toxicity	-	0.6778	67.78%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.9509	95.09%

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	95.67%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.63%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.70%	91.11%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	87.99%	92.38%
CHEMBL237	P41145	Kappa opioid receptor	87.96%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.87%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.09%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.72%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	86.22%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.13%	96.21%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	86.01%	96.03%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.56%	97.86%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.23%	98.46%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.47%	93.04%
CHEMBL3589	P55263	Adenosine kinase	82.51%	98.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.40%	95.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.34%	97.47%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	81.49%	95.61%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.15%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.87%	85.14%

Plants that contains it

• Clinopodium vulgare
• Commiphora sphaerocarpa
• Erythrina speciosa
• Helichrysum drakensbergense
• Piper divaricatum
• Prosopis africana
• Prunus prostrata
• Richteria pyrethroides
• Santolina pectinata

Cross-Links

• PubChem: 21576629
• NPASS: NPC133221