(3S,3aR,5R,8R,8aS)-8-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,8-dihydroxy-3-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-3a,4,5,6,7,8a-hexahydro-1H-azulen-2-one

Details

• Internal ID: decfa4f0-0001-4a9f-a3d9-894fc02c514b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (3S,3aR,5R,8R,8aS)-8-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,8-dihydroxy-3-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-3a,4,5,6,7,8a-hexahydro-1H-azulen-2-one
• SMILES (Canonical): CC1(C2CC(CCC(C2CC1=O)(COC3(C(C(C(O3)CO)O)O)CO)O)C(C)(C)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1([C@@H]2C[C@@H](CC[C@@]([C@H]2CC1=O)(CO[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)O)C(C)(C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C27H46O15/c1-24(2,42-23-21(35)20(34)18(32)15(8-28)40-23)12-4-5-26(38,14-7-17(31)25(3,37)13(14)6-12)11-39-27(10-30)22(36)19(33)16(9-29)41-27/h12-16,18-23,28-30,32-38H,4-11H2,1-3H3/t12-,13-,14+,15-,16-,18-,19-,20+,21-,22+,23+,25+,26+,27-/m1/s1
• InChI Key: DOVPOPWCZBPBQQ-HKSXIDQLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₁₅
• Molecular Weight: 610.60 g/mol
• Exact Mass: 610.28367076 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -4.11
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5587	55.87%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7363	73.63%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.8528	85.28%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6469	64.69%
P-glycoprotein inhibitior	-	0.4562	45.62%
P-glycoprotein substrate	-	0.6532	65.32%
CYP3A4 substrate	+	0.7116	71.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8641	86.41%
CYP3A4 inhibition	-	0.9659	96.59%
CYP2C9 inhibition	-	0.8716	87.16%
CYP2C19 inhibition	-	0.8732	87.32%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.8992	89.92%
CYP2C8 inhibition	+	0.5931	59.31%
CYP inhibitory promiscuity	-	0.9773	97.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6732	67.32%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.7289	72.89%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6899	68.99%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9063	90.63%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.4573	45.73%
Estrogen receptor binding	+	0.6301	63.01%
Androgen receptor binding	+	0.7079	70.79%
Thyroid receptor binding	-	0.5782	57.82%
Glucocorticoid receptor binding	+	0.5711	57.11%
Aromatase binding	+	0.6714	67.14%
PPAR gamma	+	0.5923	59.23%
Honey bee toxicity	-	0.6937	69.37%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.6462	64.62%

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	98.23%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.41%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.31%	96.61%
CHEMBL2996	Q05655	Protein kinase C delta	96.04%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.05%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.91%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.52%	98.95%
CHEMBL1871	P10275	Androgen Receptor	89.89%	96.43%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.97%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.55%	95.83%
CHEMBL1937	Q92769	Histone deacetylase 2	88.54%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.19%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.98%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.46%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.67%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.80%	86.33%
CHEMBL5028	O14672	ADAM10	84.33%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.13%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.69%	92.94%
CHEMBL299	P17252	Protein kinase C alpha	81.92%	98.03%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.80%	92.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.64%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.43%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.08%	95.50%

Plants that contains it

• Atractylodes lancea

Cross-Links

• PubChem: 11114722
• NPASS: NPC103648
• LOTUS: LTS0222683
• wikiData: Q104986285