(2S,3R,4S,5S,6R)-2-[2-[(2S,3S,3aR,5R,8R,8aS)-2,3,8-trihydroxy-8-(hydroxymethyl)-3-methyl-1,2,3a,4,5,6,7,8a-octahydroazulen-5-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 32e53fef-a5fe-4997-8efb-c370531d414b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-[(2S,3S,3aR,5R,8R,8aS)-2,3,8-trihydroxy-8-(hydroxymethyl)-3-methyl-1,2,3a,4,5,6,7,8a-octahydroazulen-5-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CC(CCC(C2CC1O)(CO)O)C(C)(C)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1([C@@H]2C[C@@H](CC[C@@]([C@H]2C[C@@H]1O)(CO)O)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C21H38O10/c1-19(2,31-18-17(27)16(26)15(25)13(8-22)30-18)10-4-5-21(29,9-23)12-7-14(24)20(3,28)11(12)6-10/h10-18,22-29H,4-9H2,1-3H3/t10-,11-,12+,13-,14+,15-,16+,17-,18+,20+,21+/m1/s1
• InChI Key: ZQIOVWYOYSNXID-PSWNBIAJSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₈O₁₀
• Molecular Weight: 450.50 g/mol
• Exact Mass: 450.24649740 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.15
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• CHEBI:138836
• C17859

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5063	50.63%
Caco-2	-	0.8350	83.50%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6172	61.72%
OATP2B1 inhibitior	-	0.7243	72.43%
OATP1B1 inhibitior	+	0.9025	90.25%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8921	89.21%
P-glycoprotein inhibitior	-	0.7660	76.60%
P-glycoprotein substrate	-	0.8509	85.09%
CYP3A4 substrate	+	0.6836	68.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8329	83.29%
CYP3A4 inhibition	-	0.9748	97.48%
CYP2C9 inhibition	-	0.8398	83.98%
CYP2C19 inhibition	-	0.8345	83.45%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.8589	85.89%
CYP2C8 inhibition	+	0.4530	45.30%
CYP inhibitory promiscuity	-	0.9762	97.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7218	72.18%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9422	94.22%
Skin irritation	-	0.7430	74.30%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.7453	74.53%
Human Ether-a-go-go-Related Gene inhibition	-	0.3928	39.28%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.6399	63.99%
skin sensitisation	-	0.8968	89.68%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7917	79.17%
Acute Oral Toxicity (c)	I	0.3574	35.74%
Estrogen receptor binding	+	0.5834	58.34%
Androgen receptor binding	+	0.6266	62.66%
Thyroid receptor binding	+	0.6248	62.48%
Glucocorticoid receptor binding	-	0.5490	54.90%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	+	0.5436	54.36%
Honey bee toxicity	-	0.7269	72.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4619	46.19%

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	99.59%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.60%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.27%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.19%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.28%	95.93%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	94.23%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	93.06%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.64%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.18%	97.79%
CHEMBL1871	P10275	Androgen Receptor	91.80%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.32%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.18%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.90%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.38%	89.05%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.83%	95.83%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.04%	97.86%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.03%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.66%	92.62%
CHEMBL233	P35372	Mu opioid receptor	83.62%	97.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.88%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.05%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.24%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.78%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	80.75%	95.38%

Plants that contains it

• Atractylodes lancea
• Atractylodes macrocephala

Cross-Links

• PubChem: 71448952
• NPASS: NPC175999
• LOTUS: LTS0154774
• wikiData: Q105381488