[(2R,3R,4S,5R,6S)-6-[[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-4,10-diacetyloxy-4a,9-bis(acetyloxymethyl)-5-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl]oxy]-5-acetyloxy-2-methyl-4-[(Z)-2-methylbut-2-enoyl]oxyoxan-3-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 65a59b5a-d3ae-4850-966e-aaadc1814e21
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-[[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-4,10-diacetyloxy-4a,9-bis(acetyloxymethyl)-5-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl]oxy]-5-acetyloxy-2-methyl-4-[(Z)-2-methylbut-2-enoyl]oxyoxan-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(OC(C(C1OC(=O)C(=CC)C)OC(=O)C)OC2C(C3(C(CC2(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)COC(=O)C)OC(=O)C)C)COC(=O)C)OC(=O)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1OC(=O)/C(=C\C)/C)OC(=O)C)O[C@H]2[C@@H]([C@@]3([C@@H](C[C@@]4(C(=CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H]([C@]6(C)COC(=O)C)OC(=O)C)C)C)[C@@H]3CC2(C)C)C)O)COC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C56H82O17/c1-17-29(3)48(63)71-43-31(5)67-50(45(69-35(9)60)44(43)72-49(64)30(4)18-2)73-46-47(70-36(10)61)56(28-66-33(7)58)38(25-51(46,11)12)37-19-20-40-52(13)23-22-42(68-34(8)59)53(14,27-65-32(6)57)39(52)21-24-54(40,15)55(37,16)26-41(56)62/h17-19,31,38-47,50,62H,20-28H2,1-16H3/b29-17-,30-18-/t31-,38+,39-,40-,41-,42+,43-,44+,45-,46+,47+,50+,52+,53-,54-,55-,56+/m1/s1
• InChI Key: BFRSDVHIMIIPMN-ZODPNUQUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₈₂O₁₇
• Molecular Weight: 1027.20 g/mol
• Exact Mass: 1026.55520114 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 8.20
• Atomic LogP (AlogP): 7.77
• H-Bond Acceptor: 17
• H-Bond Donor: 1
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9640	96.40%
Caco-2	-	0.8560	85.60%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8842	88.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7802	78.02%
OATP1B3 inhibitior	+	0.8424	84.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.9767	97.67%
P-glycoprotein inhibitior	+	0.7637	76.37%
P-glycoprotein substrate	+	0.5644	56.44%
CYP3A4 substrate	+	0.7331	73.31%
CYP2C9 substrate	-	0.7925	79.25%
CYP2D6 substrate	-	0.9005	90.05%
CYP3A4 inhibition	-	0.7853	78.53%
CYP2C9 inhibition	-	0.7911	79.11%
CYP2C19 inhibition	-	0.8197	81.97%
CYP2D6 inhibition	-	0.9495	94.95%
CYP1A2 inhibition	-	0.8088	80.88%
CYP2C8 inhibition	+	0.7182	71.82%
CYP inhibitory promiscuity	-	0.9530	95.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6606	66.06%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.5440	54.40%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7143	71.43%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7142	71.42%
skin sensitisation	-	0.8740	87.40%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6464	64.64%
Acute Oral Toxicity (c)	III	0.6686	66.86%
Estrogen receptor binding	+	0.7567	75.67%
Androgen receptor binding	+	0.7513	75.13%
Thyroid receptor binding	+	0.6151	61.51%
Glucocorticoid receptor binding	+	0.8073	80.73%
Aromatase binding	+	0.6703	67.03%
PPAR gamma	+	0.8210	82.10%
Honey bee toxicity	-	0.7163	71.63%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9814	98.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	98.45%	91.65%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.80%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.06%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.70%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.76%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.98%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.46%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.32%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.71%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.89%	100.00%
CHEMBL5028	O14672	ADAM10	83.77%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.43%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.99%	94.33%
CHEMBL1859	O95180	Voltage-gated T-type calcium channel alpha-1H subunit	82.24%	98.57%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.50%	82.69%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.32%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.01%	81.11%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.53%	93.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.41%	89.34%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.25%	96.77%

Plants that contains it

• Napoleonaea imperialis

Cross-Links

• PubChem: 162949853
• LOTUS: LTS0138442
• wikiData: Q104934784