NCGC00384975-01_C21H36O11_beta-D-Glucopyranoside, (1R,2S,4R,5R)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl 6-O-[(2R,3R,4R)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)-2-furanyl]-

Details

• Internal ID: 77eb47a6-6a38-4097-be5e-e2000fd350aa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 2-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(5-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl)oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CC(C1(CC2O)C)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O)C
• SMILES (Isomeric): CC1(C2CC(C1(CC2O)C)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O)C
• InChI: InChI=1S/C21H36O11/c1-19(2)9-4-12(20(19,3)5-10(9)23)32-17-15(26)14(25)13(24)11(31-17)6-29-18-16(27)21(28,7-22)8-30-18/h9-18,22-28H,4-8H2,1-3H3
• InChI Key: BVEVSYQMQABMQM-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₁₁
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.22576196 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• NCGC00384975-01_C21H36O11_beta-D-Glucopyranoside, (1R,2S,4R,5R)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl 6-O-[(2R,3R,4R)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)-2-furanyl]-
• 2-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(5-hydroxy-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl)oxy]oxane-3,4,5-triol
• Compound NP-016209
• AKOS040735325
• NCGC00384975-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6524	65.24%
Caco-2	-	0.8127	81.27%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6073	60.73%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9303	93.03%
P-glycoprotein inhibitior	-	0.7343	73.43%
P-glycoprotein substrate	-	0.7206	72.06%
CYP3A4 substrate	+	0.6758	67.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.9334	93.34%
CYP2C9 inhibition	-	0.9041	90.41%
CYP2C19 inhibition	-	0.9005	90.05%
CYP2D6 inhibition	-	0.9453	94.53%
CYP1A2 inhibition	-	0.9247	92.47%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9625	96.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.7721	77.21%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6999	69.99%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9097	90.97%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6137	61.37%
Acute Oral Toxicity (c)	I	0.5956	59.56%
Estrogen receptor binding	+	0.5860	58.60%
Androgen receptor binding	+	0.5382	53.82%
Thyroid receptor binding	+	0.5844	58.44%
Glucocorticoid receptor binding	+	0.6425	64.25%
Aromatase binding	+	0.7630	76.30%
PPAR gamma	+	0.6026	60.26%
Honey bee toxicity	-	0.7432	74.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8420	84.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	97.92%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.98%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.49%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.40%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.98%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.62%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.93%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.18%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.44%	92.86%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.43%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.41%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.10%	94.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	82.83%	92.32%
CHEMBL221	P23219	Cyclooxygenase-1	82.71%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.10%	96.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.48%	96.61%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.08%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.07%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.90%	89.00%

Plants that contains it

• Glehnia littoralis
• Tinospora cordifolia

Cross-Links

• PubChem: 51136374
• LOTUS: LTS0249307
• wikiData: Q104946488