2-[(1S,2R,3S,4R,7S,9S,11S,12S,14S,17R,18R,19R,21R,22S)-2,11-dihydroxy-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-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: fda3472a-3140-420c-9873-9cb81e14f5ab
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: 2-[(1S,2R,3S,4R,7S,9S,11S,12S,14S,17R,18R,19R,21R,22S)-2,11-dihydroxy-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-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(CCC56CC57C(CCC6C4(C3O)C)C(C(CC7O)OC8C(C(C(CO8)O)O)O)(C)C)C)O2)C(C)(C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@]57[C@@H](CC[C@H]6[C@@]4([C@H]3O)C)C([C@H](C[C@@H]7O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)(C)C)C)O2)C(C)(C)OC(=O)C
• InChI: InChI=1S/C37H58O11/c1-17-13-20-28(32(5,6)46-18(2)38)48-37(47-20)27(17)33(7)11-12-35-16-36(35)21(9-10-22(35)34(33,8)30(37)43)31(3,4)24(14-23(36)40)45-29-26(42)25(41)19(39)15-44-29/h17,19-30,39-43H,9-16H2,1-8H3/t17-,19-,20-,21+,22+,23+,24+,25+,26-,27-,28+,29+,30-,33-,34-,35+,36-,37+/m1/s1
• InChI Key: CWQHVTSRILDLMJ-FTGQJZMTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₁
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.39791266 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8059	80.59%
Caco-2	-	0.8617	86.17%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7464	74.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8553	85.53%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.6250	62.50%
P-glycoprotein inhibitior	+	0.7561	75.61%
P-glycoprotein substrate	+	0.6494	64.94%
CYP3A4 substrate	+	0.7330	73.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.8545	85.45%
CYP2C9 inhibition	-	0.7963	79.63%
CYP2C19 inhibition	-	0.8638	86.38%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8662	86.62%
CYP2C8 inhibition	+	0.7362	73.62%
CYP inhibitory promiscuity	-	0.9663	96.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6383	63.83%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9130	91.30%
Skin irritation	-	0.6519	65.19%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6931	69.31%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8895	88.95%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7373	73.73%
Acute Oral Toxicity (c)	I	0.4074	40.74%
Estrogen receptor binding	+	0.5833	58.33%
Androgen receptor binding	+	0.7537	75.37%
Thyroid receptor binding	-	0.5724	57.24%
Glucocorticoid receptor binding	+	0.6224	62.24%
Aromatase binding	+	0.7062	70.62%
PPAR gamma	+	0.6663	66.63%
Honey bee toxicity	-	0.6321	63.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9378	93.78%

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	99.41%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.78%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.35%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.16%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.25%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.88%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.67%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.13%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.68%	91.24%
CHEMBL1914	P06276	Butyrylcholinesterase	89.18%	95.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.03%	97.14%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.32%	85.31%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.09%	95.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.41%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.32%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.46%	92.88%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.29%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.09%	89.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.80%	89.34%
CHEMBL5255	O00206	Toll-like receptor 4	84.97%	92.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.74%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.71%	89.00%
CHEMBL259	P32245	Melanocortin receptor 4	82.73%	95.38%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.36%	93.04%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.09%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.05%	100.00%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.64%	98.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.43%	94.45%
CHEMBL1902	P62942	FK506-binding protein 1A	80.43%	97.05%

Plants that contains it

• Actaea simplex

Cross-Links

• PubChem: 15225907
• LOTUS: LTS0225033
• wikiData: Q104971462