(3S,3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(E)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-en-2-yl]-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one

Details

• Internal ID: 70e6a7df-5747-40ca-a5f3-15926c653a4a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (3S,3aR,4S,6S,7R,7aR)-6-ethenyl-4-hydroxy-3,6-dimethyl-7-[(E)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-en-2-yl]-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one
• SMILES (Canonical): CC1C2C(CC(C(C2OC1=O)C(=COC3C(C(C(C(O3)CO)O)O)O)C)(C)C=C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@@]([C@@H]([C@H]2OC1=O)/C(=C/O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)/C)(C)C=C)O
• InChI: InChI=1S/C21H32O9/c1-5-21(4)6-11(23)13-10(3)19(27)30-18(13)14(21)9(2)8-28-20-17(26)16(25)15(24)12(7-22)29-20/h5,8,10-18,20,22-26H,1,6-7H2,2-4H3/b9-8+/t10-,11-,12+,13+,14+,15+,16-,17+,18-,20+,21+/m0/s1
• InChI Key: PNUZTGLWURTQTO-YHBSBXERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₉
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.20463259 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7345	73.45%
Caco-2	-	0.8035	80.35%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6239	62.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8607	86.07%
OATP1B3 inhibitior	+	0.9153	91.53%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6101	61.01%
P-glycoprotein inhibitior	-	0.7500	75.00%
P-glycoprotein substrate	-	0.7078	70.78%
CYP3A4 substrate	+	0.6396	63.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.7623	76.23%
CYP2C9 inhibition	-	0.8871	88.71%
CYP2C19 inhibition	-	0.8953	89.53%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.8865	88.65%
CYP2C8 inhibition	-	0.8076	80.76%
CYP inhibitory promiscuity	-	0.8188	81.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5854	58.54%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9672	96.72%
Skin irritation	-	0.6045	60.45%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3970	39.70%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6612	66.12%
skin sensitisation	-	0.8353	83.53%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6557	65.57%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.7281	72.81%
Androgen receptor binding	+	0.5543	55.43%
Thyroid receptor binding	+	0.5960	59.60%
Glucocorticoid receptor binding	+	0.6050	60.50%
Aromatase binding	+	0.5323	53.23%
PPAR gamma	+	0.5172	51.72%
Honey bee toxicity	-	0.5900	59.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8663	86.63%

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	98.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.32%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	90.18%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.93%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.60%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.99%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.64%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.79%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.72%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.64%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.53%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.48%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.01%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.52%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.86%	89.34%
CHEMBL1937	Q92769	Histone deacetylase 2	81.20%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.91%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	80.30%	91.49%

Plants that contains it

• Cichorium endivia

Cross-Links

• PubChem: 102476819
• LOTUS: LTS0201004
• wikiData: Q105212220