2-[9-[4,5-Dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yl acetate

Details

• Internal ID: a409e589-9d0f-460c-8f63-e7a1c0a6c28f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: 2-[9-[4,5-dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yl acetate
• SMILES (Canonical): CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)O2)C(C)(C)OC(=O)C
• SMILES (Isomeric): CC1CC2C(OC3(C1C4(CCC56CC57CCC(C(C7CCC6C4(C3O)C)(C)C)OC8C(C(C(CO8)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)O2)C(C)(C)OC(=O)C
• InChI: InChI=1S/C43H68O15/c1-19-15-22-33(38(5,6)56-20(2)45)58-43(57-22)32(19)39(7)13-14-42-18-41(42)12-11-26(37(3,4)24(41)9-10-25(42)40(39,8)36(43)51)54-35-31(27(47)21(46)17-52-35)55-34-30(50)29(49)28(48)23(16-44)53-34/h19,21-36,44,46-51H,9-18H2,1-8H3
• InChI Key: XWZIOEXOWFDMDQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₈O₁₅
• Molecular Weight: 825.00 g/mol
• Exact Mass: 824.45582146 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6585	65.85%
Caco-2	-	0.8815	88.15%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7127	71.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8159	81.59%
OATP1B3 inhibitior	+	0.9309	93.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.4591	45.91%
P-glycoprotein inhibitior	+	0.7650	76.50%
P-glycoprotein substrate	+	0.6012	60.12%
CYP3A4 substrate	+	0.7380	73.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.8878	88.78%
CYP2C9 inhibition	-	0.7949	79.49%
CYP2C19 inhibition	-	0.8408	84.08%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.8980	89.80%
CYP2C8 inhibition	+	0.7462	74.62%
CYP inhibitory promiscuity	-	0.9594	95.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6516	65.16%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.6862	68.62%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7967	79.67%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9102	91.02%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7695	76.95%
Acute Oral Toxicity (c)	I	0.6254	62.54%
Estrogen receptor binding	+	0.7133	71.33%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	-	0.5701	57.01%
Glucocorticoid receptor binding	+	0.6909	69.09%
Aromatase binding	+	0.7080	70.80%
PPAR gamma	+	0.7546	75.46%
Honey bee toxicity	-	0.6116	61.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8780	87.80%

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	99.52%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.25%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.93%	91.24%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.84%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.47%	89.34%
CHEMBL2581	P07339	Cathepsin D	93.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.74%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	92.52%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.20%	96.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.36%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	89.21%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.13%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.00%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.97%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.36%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	86.98%	92.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.05%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.89%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.16%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.08%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.60%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	84.49%	95.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.61%	94.33%
CHEMBL2996	Q05655	Protein kinase C delta	83.31%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.14%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.82%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	82.17%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.13%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.90%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.76%	96.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.64%	89.50%
CHEMBL5028	O14672	ADAM10	80.33%	97.50%

Plants that contains it

• Actaea cimicifuga

Cross-Links

• PubChem: 163041088
• LOTUS: LTS0014475
• wikiData: Q105343892