[(2S,3R,4S,5R)-2-[[(1S,4R,5R,6R,8R,10R,12S,13R,16R,18S,21R)-8-[(1S)-1-acetyloxy-2-hydroxy-2-methylpropyl]-4,6,12,17,17-pentamethyl-11-oxo-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-18-yl]oxy]-4,5-dihydroxyoxan-3-yl] acetate

Details

• Internal ID: b5a3bd5e-e65b-446b-ba49-75948856c038
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,3R,4S,5R)-2-[[(1S,4R,5R,6R,8R,10R,12S,13R,16R,18S,21R)-8-[(1S)-1-acetyloxy-2-hydroxy-2-methylpropyl]-4,6,12,17,17-pentamethyl-11-oxo-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-18-yl]oxy]-4,5-dihydroxyoxan-3-yl] acetate
• SMILES (Canonical): CC1CC(OC2C1C3(CCC45CC46CCC(C(C6CCC5C3(C2=O)C)(C)C)OC7C(C(C(CO7)O)O)OC(=O)C)C)C(C(C)(C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H](O[C@@H]2[C@H]1[C@]3(CC[C@@]45C[C@@]46CC[C@@H](C([C@@H]6CC[C@H]5[C@@]3(C2=O)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)OC(=O)C)C)[C@@H](C(C)(C)O)OC(=O)C
• InChI: InChI=1S/C39H60O11/c1-19-16-23(32(35(6,7)45)48-21(3)41)49-29-27(19)36(8)14-15-39-18-38(39)13-12-26(50-33-30(47-20(2)40)28(43)22(42)17-46-33)34(4,5)24(38)10-11-25(39)37(36,9)31(29)44/h19,22-30,32-33,42-43,45H,10-18H2,1-9H3/t19-,22-,23-,24+,25+,26+,27+,28+,29-,30-,32+,33+,36-,37-,38-,39+/m1/s1
• InChI Key: HOEACCWXJIUNFZ-PJDTTXJDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₀O₁₁
• Molecular Weight: 704.90 g/mol
• Exact Mass: 704.41356273 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8517	85.17%
Caco-2	-	0.8650	86.50%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8068	80.68%
OATP2B1 inhibitior	-	0.8702	87.02%
OATP1B1 inhibitior	+	0.8184	81.84%
OATP1B3 inhibitior	+	0.8897	88.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5154	51.54%
P-glycoprotein inhibitior	+	0.7892	78.92%
P-glycoprotein substrate	+	0.5965	59.65%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.8032	80.32%
CYP2C19 inhibition	-	0.8742	87.42%
CYP2D6 inhibition	-	0.9605	96.05%
CYP1A2 inhibition	-	0.8133	81.33%
CYP2C8 inhibition	+	0.6644	66.44%
CYP inhibitory promiscuity	-	0.9857	98.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6567	65.67%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.6490	64.90%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4355	43.55%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5754	57.54%
skin sensitisation	-	0.9030	90.30%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7150	71.50%
Acute Oral Toxicity (c)	I	0.3493	34.93%
Estrogen receptor binding	+	0.6562	65.62%
Androgen receptor binding	+	0.7285	72.85%
Thyroid receptor binding	-	0.5508	55.08%
Glucocorticoid receptor binding	+	0.7573	75.73%
Aromatase binding	+	0.7178	71.78%
PPAR gamma	+	0.7206	72.06%
Honey bee toxicity	-	0.6208	62.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9567	95.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.29%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.84%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	96.70%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.39%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.49%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.87%	97.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.36%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.27%	92.88%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	90.10%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.89%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	89.61%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.27%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.21%	97.09%
CHEMBL5028	O14672	ADAM10	85.74%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.81%	97.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.88%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.15%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.23%	92.50%
CHEMBL204	P00734	Thrombin	80.51%	96.01%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.36%	85.14%

Plants that contains it

• Actaea vaginata
• Dicranopteris linearis

Cross-Links

• PubChem: 12096379
• NPASS: NPC101118
• LOTUS: LTS0007171
• wikiData: Q105031218