(1S,2S,4R,6R,8S,9R,10R,13R,14R)-16-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-(1,2-dihydroxy-2-methylpropyl)-8-hydroxy-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-15,19-diene-12,17-dione

Details

• Internal ID: 2217c2be-c15b-4e37-bddf-7ad37d9e5f66
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (1S,2S,4R,6R,8S,9R,10R,13R,14R)-16-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-(1,2-dihydroxy-2-methylpropyl)-8-hydroxy-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-15,19-diene-12,17-dione
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC4C(=CCC5C4(C(=O)CC6(C5(CC7C6C(CC(O7)C(C(C)(C)O)O)(C)O)C)C)C)C(C3=O)(C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C[C@@H]4C(=CC[C@@H]5[C@]4(C(=O)C[C@]6([C@]5(C[C@@H]7[C@@H]6[C@@](C[C@@H](O7)C(C(C)(C)O)O)(C)O)C)C)C)C(C3=O)(C)C)CO)O)O)O)O)O
• InChI: InChI=1S/C42H64O16/c1-17-26(45)28(47)30(49)35(54-17)58-31-29(48)27(46)23(16-43)57-36(31)56-20-12-19-18(37(2,3)33(20)50)10-11-24-39(6)13-21-32(40(39,7)15-25(44)42(19,24)9)41(8,53)14-22(55-21)34(51)38(4,5)52/h10,12,17,19,21-24,26-32,34-36,43,45-49,51-53H,11,13-16H2,1-9H3/t17-,19+,21+,22+,23+,24-,26-,27+,28+,29-,30+,31+,32-,34?,35-,36+,39-,40+,41-,42-/m0/s1
• InChI Key: LJIPHELFYSCLEX-KYUXAHQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₁₆
• Molecular Weight: 824.90 g/mol
• Exact Mass: 824.41943595 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8846	88.46%
Caco-2	-	0.8759	87.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8269	82.69%
OATP2B1 inhibitior	-	0.8702	87.02%
OATP1B1 inhibitior	+	0.8448	84.48%
OATP1B3 inhibitior	+	0.8486	84.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7641	76.41%
P-glycoprotein inhibitior	+	0.7535	75.35%
P-glycoprotein substrate	+	0.6218	62.18%
CYP3A4 substrate	+	0.7247	72.47%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8874	88.74%
CYP3A4 inhibition	-	0.7876	78.76%
CYP2C9 inhibition	-	0.8706	87.06%
CYP2C19 inhibition	-	0.9387	93.87%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.9154	91.54%
CYP2C8 inhibition	+	0.6964	69.64%
CYP inhibitory promiscuity	-	0.9389	93.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6036	60.36%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.5373	53.73%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7588	75.88%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6019	60.19%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5837	58.37%
Acute Oral Toxicity (c)	III	0.5532	55.32%
Estrogen receptor binding	+	0.7673	76.73%
Androgen receptor binding	+	0.7364	73.64%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7602	76.02%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.7776	77.76%
Honey bee toxicity	-	0.6474	64.74%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9792	97.92%

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	99.12%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.69%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.22%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.07%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.01%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.32%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.05%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.56%	96.61%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.74%	87.67%
CHEMBL3401	O75469	Pregnane X receptor	87.79%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.86%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.75%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.48%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.45%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.87%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.84%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.67%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.53%	91.07%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.14%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.69%	91.24%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.60%	98.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.23%	97.36%

Plants that contains it

• Trichosanthes tricuspidata

Cross-Links

• PubChem: 6325481
• LOTUS: LTS0191363
• wikiData: Q105152608