[(2S,3R,4R,5S,6R)-5-benzoyloxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6S,7S,8aR)-7-acetyloxy-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

Details

• Internal ID: 7cebdc47-141b-4a96-9068-5e762a8d56fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3R,4R,5S,6R)-5-benzoyloxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aR,5R,6S,7S,8aR)-7-acetyloxy-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate
• SMILES (Canonical): CC1C(CC2(C(C1(C)CCC3=CCOC3=O)CCC=C2C(=O)OC4C(C(C(C(O4)CO)OC(=O)C5=CC=CC=C5)O)O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@@]2([C@@H]([C@@]1(C)CCC3=CCOC3=O)CCC=C2C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)OC(=O)C5=CC=CC=C5)O)O)C)OC(=O)C
• InChI: InChI=1S/C35H44O12/c1-19-24(44-20(2)37)17-35(4)23(11-8-12-26(35)34(19,3)15-13-22-14-16-43-30(22)40)32(42)47-33-28(39)27(38)29(25(18-36)45-33)46-31(41)21-9-6-5-7-10-21/h5-7,9-11,14,19,24-29,33,36,38-39H,8,12-13,15-18H2,1-4H3/t19-,24+,25-,26-,27-,28-,29-,33+,34+,35+/m1/s1
• InChI Key: WIGMMRHBQLFVJD-WYSFLSORSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₂
• Molecular Weight: 656.70 g/mol
• Exact Mass: 656.28327683 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8264	82.64%
Caco-2	-	0.8616	86.16%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8422	84.22%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.8407	84.07%
OATP1B3 inhibitior	+	0.8974	89.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.8111	81.11%
P-glycoprotein inhibitior	+	0.7529	75.29%
P-glycoprotein substrate	+	0.5901	59.01%
CYP3A4 substrate	+	0.7090	70.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8824	88.24%
CYP3A4 inhibition	-	0.6615	66.15%
CYP2C9 inhibition	-	0.9092	90.92%
CYP2C19 inhibition	-	0.8793	87.93%
CYP2D6 inhibition	-	0.9324	93.24%
CYP1A2 inhibition	-	0.7630	76.30%
CYP2C8 inhibition	+	0.6765	67.65%
CYP inhibitory promiscuity	-	0.8721	87.21%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4544	45.44%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9268	92.68%
Skin irritation	-	0.5257	52.57%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4935	49.35%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5694	56.94%
skin sensitisation	-	0.9148	91.48%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4787	47.87%
Acute Oral Toxicity (c)	I	0.6506	65.06%
Estrogen receptor binding	+	0.7939	79.39%
Androgen receptor binding	+	0.6921	69.21%
Thyroid receptor binding	-	0.5163	51.63%
Glucocorticoid receptor binding	+	0.7767	77.67%
Aromatase binding	+	0.6635	66.35%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.7045	70.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.50%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.29%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.15%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.37%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.71%	97.25%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.31%	83.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.24%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.49%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.31%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.38%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.84%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.64%	99.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.25%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.19%	100.00%
CHEMBL5028	O14672	ADAM10	82.68%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.82%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.65%	94.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.47%	93.00%

Plants that contains it

• Onoseris alata

Cross-Links

• PubChem: 100989381
• LOTUS: LTS0115163
• wikiData: Q105306218