(3R,4aR,5S,6S,8aR)-6-hydroxy-3-(2-hydroxypropan-2-yl)-5,8a-dimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-one

Details

• Internal ID: 62519a86-6c40-45ab-81e0-effbe2db1ae5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (3R,4aR,5S,6S,8aR)-6-hydroxy-3-(2-hydroxypropan-2-yl)-5,8a-dimethyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-one
• SMILES (Canonical): CC12CCC(C(C1CC(C(=O)C2)C(C)(C)O)(C)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@@]([C@@H]1C[C@@H](C(=O)C2)C(C)(C)O)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C21H36O9/c1-19(2,28)10-7-13-20(3,8-11(10)23)6-5-14(24)21(13,4)30-18-17(27)16(26)15(25)12(9-22)29-18/h10,12-18,22,24-28H,5-9H2,1-4H3/t10-,12+,13+,14-,15+,16-,17+,18-,20+,21-/m0/s1
• InChI Key: OEXMOKNCZIWALN-UUVGVEKZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₉
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.23593272 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6965	69.65%
Caco-2	-	0.7782	77.82%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8055	80.55%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.8977	89.77%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	-	0.8336	83.36%
P-glycoprotein inhibitior	-	0.7989	79.89%
P-glycoprotein substrate	-	0.8329	83.29%
CYP3A4 substrate	+	0.6783	67.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8646	86.46%
CYP3A4 inhibition	-	0.8108	81.08%
CYP2C9 inhibition	-	0.8488	84.88%
CYP2C19 inhibition	-	0.8940	89.40%
CYP2D6 inhibition	-	0.9631	96.31%
CYP1A2 inhibition	-	0.7964	79.64%
CYP2C8 inhibition	-	0.6413	64.13%
CYP inhibitory promiscuity	-	0.9739	97.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7567	75.67%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9677	96.77%
Skin irritation	-	0.6841	68.41%
Skin corrosion	-	0.9577	95.77%
Ames mutagenesis	-	0.6724	67.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5968	59.68%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9207	92.07%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7050	70.50%
Acute Oral Toxicity (c)	III	0.6208	62.08%
Estrogen receptor binding	-	0.4931	49.31%
Androgen receptor binding	+	0.5967	59.67%
Thyroid receptor binding	+	0.6446	64.46%
Glucocorticoid receptor binding	-	0.5384	53.84%
Aromatase binding	+	0.6162	61.62%
PPAR gamma	-	0.5136	51.36%
Honey bee toxicity	-	0.7536	75.36%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8743	87.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.41%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.63%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.05%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	90.62%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.75%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	87.47%	83.82%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.43%	93.04%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.75%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.44%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	85.80%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.78%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.52%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.44%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.90%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.02%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.00%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.75%	89.34%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.41%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.38%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.33%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.26%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.97%	97.14%
CHEMBL237	P41145	Kappa opioid receptor	81.24%	98.10%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.64%	86.92%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.10%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.06%	94.73%

Plants that contains it

• Tessaria integrifolia

Cross-Links

• PubChem: 10812635
• LOTUS: LTS0254065
• wikiData: Q105190646