[5-ethenyl-4a,5-dimethyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-3-yl] (2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoate

Details

• Internal ID: ef4cd181-ca34-42d8-868a-31631dfb619c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [5-ethenyl-4a,5-dimethyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-3-yl] (2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoate
• SMILES (Canonical): CC(=CCCC(C)(C=C)O)C(=O)OC1CC2(C(=COC(C2(C)C=C)OC3C(C(C(C(O3)CO)O)O)O)C(=O)O1)C
• SMILES (Isomeric): C/C(=C\CCC(C)(C=C)O)/C(=O)OC1CC2(C(=COC(C2(C)C=C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O1)C
• InChI: InChI=1S/C28H40O12/c1-7-26(4,35)11-9-10-15(3)22(33)38-18-12-28(6)16(23(34)39-18)14-36-25(27(28,5)8-2)40-24-21(32)20(31)19(30)17(13-29)37-24/h7-8,10,14,17-21,24-25,29-32,35H,1-2,9,11-13H2,3-6H3/b15-10+/t17-,18?,19-,20+,21-,24+,25?,26?,27?,28?/m1/s1
• InChI Key: BSSCPLRQUUGNAR-WMLOERPTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₂
• Molecular Weight: 568.60 g/mol
• Exact Mass: 568.25197671 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7286	72.86%
Caco-2	-	0.8414	84.14%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7570	75.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8150	81.50%
OATP1B3 inhibitior	-	0.2160	21.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6048	60.48%
BSEP inhibitior	+	0.8586	85.86%
P-glycoprotein inhibitior	+	0.6577	65.77%
P-glycoprotein substrate	-	0.5407	54.07%
CYP3A4 substrate	+	0.7031	70.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8807	88.07%
CYP3A4 inhibition	-	0.6336	63.36%
CYP2C9 inhibition	-	0.8645	86.45%
CYP2C19 inhibition	-	0.9159	91.59%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8723	87.23%
CYP2C8 inhibition	+	0.6099	60.99%
CYP inhibitory promiscuity	-	0.9480	94.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6220	62.20%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9262	92.62%
Skin irritation	+	0.4896	48.96%
Skin corrosion	-	0.9260	92.60%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4160	41.60%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5591	55.91%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5589	55.89%
Acute Oral Toxicity (c)	III	0.7408	74.08%
Estrogen receptor binding	+	0.6974	69.74%
Androgen receptor binding	+	0.6870	68.70%
Thyroid receptor binding	-	0.4932	49.32%
Glucocorticoid receptor binding	+	0.6123	61.23%
Aromatase binding	+	0.6334	63.34%
PPAR gamma	+	0.6678	66.78%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9055	90.55%

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	98.26%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.23%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.87%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.42%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.18%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.59%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.71%	91.07%
CHEMBL2581	P07339	Cathepsin D	86.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.11%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.44%	91.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.20%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.99%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.28%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.52%	99.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.29%	96.47%
CHEMBL5028	O14672	ADAM10	81.40%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.15%	97.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.10%	89.34%

Plants that contains it

• Juncus effusus

Cross-Links

• PubChem: 5319368
• NPASS: NPC45965