methyl (4S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 46a338ee-ef78-465b-afbd-e625bf66cce4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(=O)OCC2C(=O)OC)OC(=O)C3=COC(C(C3CC=O)C=C)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1C(=O)OC[C@H]2C(=O)OC)OC(=O)C3=CO[C@H]([C@@H]([C@@H]3CC=O)C=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C27H36O14/c1-4-12-13(5-6-28)15(10-38-26(12)41-27-22(32)21(31)20(30)18(8-29)40-27)24(34)39-17-7-14-16(23(33)36-3)9-37-25(35)19(14)11(17)2/h4,6,10-14,16-22,26-27,29-32H,1,5,7-9H2,2-3H3/t11-,12+,13-,14+,16+,17-,18+,19+,20+,21-,22+,26-,27-/m0/s1
• InChI Key: PZZBYEOFJHWZID-SOOXGXIGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₄
• Molecular Weight: 584.60 g/mol
• Exact Mass: 584.21050582 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.42
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8746	87.46%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6924	69.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7732	77.32%
OATP1B3 inhibitior	+	0.9549	95.49%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6227	62.27%
P-glycoprotein inhibitior	-	0.4402	44.02%
P-glycoprotein substrate	+	0.6603	66.03%
CYP3A4 substrate	+	0.7065	70.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.8106	81.06%
CYP2C9 inhibition	-	0.9109	91.09%
CYP2C19 inhibition	-	0.8546	85.46%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8975	89.75%
CYP2C8 inhibition	+	0.6259	62.59%
CYP inhibitory promiscuity	-	0.8805	88.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7212	72.12%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.7381	73.81%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5869	58.69%
Human Ether-a-go-go-Related Gene inhibition	+	0.8360	83.60%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8600	86.00%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7834	78.34%
Acute Oral Toxicity (c)	III	0.5211	52.11%
Estrogen receptor binding	+	0.7490	74.90%
Androgen receptor binding	+	0.6690	66.90%
Thyroid receptor binding	-	0.6003	60.03%
Glucocorticoid receptor binding	+	0.5741	57.41%
Aromatase binding	-	0.5100	51.00%
PPAR gamma	+	0.5753	57.53%
Honey bee toxicity	-	0.6511	65.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9168	91.68%

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	97.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.30%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.20%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.95%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.03%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.49%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.42%	96.00%
CHEMBL4530	P00488	Coagulation factor XIII	84.34%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.15%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	84.12%	91.19%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.93%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.35%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.66%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.16%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.09%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.99%	98.95%
CHEMBL5028	O14672	ADAM10	81.21%	97.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.44%	94.80%

Plants that contains it

• Scaevola racemigera

Cross-Links

• PubChem: 101425397
• LOTUS: LTS0105701
• wikiData: Q105217255