[(4aS,5R,5'S,6R,8R)-5'-(furan-3-yl)-6-methyl-2'-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-5,3'-oxolane]-1-yl]methyl acetate

Details

• Internal ID: eda65e93-a0c7-41a6-bcb3-65d644613cf3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(4aS,5R,5'S,6R,8R)-5'-(furan-3-yl)-6-methyl-2'-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-5,3'-oxolane]-1-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2=C(CCCC2C13CC(OC3=O)C4=COC=C4)COC(=O)C)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@H](C2=C(CCC[C@@H]2[C@@]13C[C@H](OC3=O)C4=COC=C4)COC(=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H36O11/c1-13-8-18(36-25-24(32)23(31)22(30)20(10-28)37-25)21-16(12-35-14(2)29)4-3-5-17(21)27(13)9-19(38-26(27)33)15-6-7-34-11-15/h6-7,11,13,17-20,22-25,28,30-32H,3-5,8-10,12H2,1-2H3/t13-,17+,18-,19+,20-,22-,23+,24-,25-,27-/m1/s1
• InChI Key: HQWNBPDSSUVDMC-SUAWGPNASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₁
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.22576196 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8527	85.27%
Caco-2	-	0.8560	85.60%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8827	88.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7549	75.49%
OATP1B3 inhibitior	+	0.8957	89.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8194	81.94%
P-glycoprotein inhibitior	-	0.4780	47.80%
P-glycoprotein substrate	-	0.5353	53.53%
CYP3A4 substrate	+	0.6963	69.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.7758	77.58%
CYP2C9 inhibition	-	0.8870	88.70%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.8501	85.01%
CYP2C8 inhibition	+	0.6276	62.76%
CYP inhibitory promiscuity	-	0.8340	83.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5407	54.07%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9457	94.57%
Skin irritation	-	0.6254	62.54%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6819	68.19%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5072	50.72%
skin sensitisation	-	0.9197	91.97%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5780	57.80%
Acute Oral Toxicity (c)	I	0.7338	73.38%
Estrogen receptor binding	+	0.8218	82.18%
Androgen receptor binding	+	0.6537	65.37%
Thyroid receptor binding	-	0.5978	59.78%
Glucocorticoid receptor binding	+	0.6790	67.90%
Aromatase binding	+	0.6152	61.52%
PPAR gamma	+	0.5885	58.85%
Honey bee toxicity	-	0.7375	73.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.62%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.03%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.38%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.00%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.48%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.85%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	89.07%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.83%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.51%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.06%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.61%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.26%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.79%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.64%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.17%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.59%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.57%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.23%	100.00%

Plants that contains it

• Teucrium flavum

Cross-Links

• PubChem: 101288299
• LOTUS: LTS0203312
• wikiData: Q105032477