[(8aalpha)-Octahydro-1beta,6alpha,7beta-trihydroxyindolizin]-8alpha-yl beta-D-glucopyranoside

Details

• Internal ID: e6e65fab-a92a-4197-822a-b3ed128eb8e4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1S,6S,7R,8R,8aR)-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7-triol
• SMILES (Canonical): C1CN2CC(C(C(C2C1O)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C14H25NO9/c16-4-7-10(20)11(21)12(22)14(23-7)24-13-8-5(17)1-2-15(8)3-6(18)9(13)19/h5-14,16-22H,1-4H2/t5-,6-,7+,8+,9+,10+,11-,12+,13+,14-/m0/s1
• InChI Key: GKBHOUDSQKMYLD-TZOWDGQSSA-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: 3

Synonyms

• [(8aalpha)-Octahydro-1beta,6alpha,7beta-trihydroxyindolizin]-8alpha-yl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5832	58.32%
Caco-2	-	0.8597	85.97%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Lysosomes	0.5508	55.08%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9350	93.50%
OATP1B3 inhibitior	+	0.9443	94.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9655	96.55%
P-glycoprotein inhibitior	-	0.9147	91.47%
P-glycoprotein substrate	-	0.8991	89.91%
CYP3A4 substrate	+	0.5340	53.40%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.7005	70.05%
CYP3A4 inhibition	-	0.9862	98.62%
CYP2C9 inhibition	-	0.9268	92.68%
CYP2C19 inhibition	-	0.9227	92.27%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.8127	81.27%
CYP2C8 inhibition	-	0.9382	93.82%
CYP inhibitory promiscuity	-	0.9685	96.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6091	60.91%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9625	96.25%
Skin irritation	-	0.7651	76.51%
Skin corrosion	-	0.9256	92.56%
Ames mutagenesis	-	0.8270	82.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4205	42.05%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5200	52.00%
skin sensitisation	-	0.8889	88.89%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6994	69.94%
Acute Oral Toxicity (c)	III	0.5001	50.01%
Estrogen receptor binding	-	0.8195	81.95%
Androgen receptor binding	-	0.6937	69.37%
Thyroid receptor binding	+	0.5691	56.91%
Glucocorticoid receptor binding	-	0.8418	84.18%
Aromatase binding	+	0.5367	53.67%
PPAR gamma	-	0.5327	53.27%
Honey bee toxicity	-	0.7030	70.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.9297	92.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.36%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.65%	91.11%
CHEMBL237	P41145	Kappa opioid receptor	89.17%	98.10%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	88.98%	96.03%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	88.50%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.42%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.17%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.47%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	84.84%	95.93%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	83.46%	92.38%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.18%	98.46%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.87%	97.86%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.63%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.40%	96.61%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.22%	97.47%
CHEMBL3589	P55263	Adenosine kinase	81.92%	98.05%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	80.46%	95.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.28%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.20%	98.95%
CHEMBL3105	P09874	Poly [ADP-ribose] polymerase-1	80.18%	93.90%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.07%	96.21%

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: 10089286
• NPASS: NPC52378