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

Details

• Internal ID: 20597fe2-3078-4713-8633-dc3f896bbcd2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(1S)-1-[(1S,4R,5R,6R,8R,10R,11R,12S,13R,16R,18S,21R)-10,11-dihydroxy-4,6,12,17,17-pentamethyl-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-8-yl]-2-hydroxy-2-methylpropyl] acetate
• SMILES (Canonical): CC1CC(OC2(C1C3(CCC45CC46CCC(C(C6CCC5C3(C2O)C)(C)C)OC7C(C(C(CO7)O)O)O)C)O)C(C(C)(C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H](O[C@@]2([C@H]1[C@]3(CC[C@@]45C[C@@]46CC[C@@H](C([C@@H]6CC[C@H]5[C@@]3([C@H]2O)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)C)O)[C@@H](C(C)(C)O)OC(=O)C
• InChI: InChI=1S/C37H60O11/c1-18-15-21(28(32(5,6)43)46-19(2)38)48-37(44)27(18)33(7)13-14-36-17-35(36)12-11-24(47-29-26(41)25(40)20(39)16-45-29)31(3,4)22(35)9-10-23(36)34(33,8)30(37)42/h18,20-30,39-44H,9-17H2,1-8H3/t18-,20-,21-,22+,23+,24+,25+,26-,27-,28+,29+,30-,33-,34-,35-,36+,37-/m1/s1
• InChI Key: PJGMIZSCETWMLA-USIWENNYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₀O₁₁
• Molecular Weight: 680.90 g/mol
• Exact Mass: 680.41356273 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7645	76.45%
Caco-2	-	0.8616	86.16%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7323	73.23%
OATP2B1 inhibitior	-	0.7332	73.32%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.9168	91.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7866	78.66%
P-glycoprotein inhibitior	+	0.7691	76.91%
P-glycoprotein substrate	+	0.6212	62.12%
CYP3A4 substrate	+	0.7303	73.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8759	87.59%
CYP3A4 inhibition	-	0.9010	90.10%
CYP2C9 inhibition	-	0.8004	80.04%
CYP2C19 inhibition	-	0.8732	87.32%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.8400	84.00%
CYP2C8 inhibition	+	0.7305	73.05%
CYP inhibitory promiscuity	-	0.9767	97.67%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6815	68.15%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.6513	65.13%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6824	68.24%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6716	67.16%
skin sensitisation	-	0.8913	89.13%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7113	71.13%
Acute Oral Toxicity (c)	III	0.3650	36.50%
Estrogen receptor binding	+	0.5506	55.06%
Androgen receptor binding	+	0.7231	72.31%
Thyroid receptor binding	-	0.5614	56.14%
Glucocorticoid receptor binding	+	0.6318	63.18%
Aromatase binding	+	0.7000	70.00%
PPAR gamma	+	0.6511	65.11%
Honey bee toxicity	-	0.6418	64.18%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9260	92.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	400 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.46%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	96.15%	98.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.94%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.53%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.35%	89.34%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.99%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.00%	97.14%
CHEMBL2581	P07339	Cathepsin D	91.73%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.51%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	91.37%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.13%	85.14%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.11%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.23%	97.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	90.08%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	89.94%	89.50%
CHEMBL3837	P07711	Cathepsin L	89.84%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.37%	89.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	88.46%	95.69%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.12%	92.86%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.50%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.97%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.51%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.26%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.29%	91.07%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.96%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.87%	92.94%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.81%	97.28%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.80%	94.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.19%	97.79%
CHEMBL5028	O14672	ADAM10	82.08%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	81.94%	95.93%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.59%	91.03%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.51%	82.50%
CHEMBL1902	P62942	FK506-binding protein 1A	81.48%	97.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.07%	92.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.82%	97.21%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.70%	91.24%

Plants that contains it

• Actaea pachypoda
• Actaea yunnanensis

Cross-Links

• PubChem: 58901565
• LOTUS: LTS0082903
• wikiData: Q105209942