(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-15-[(E,2R)-6-hydroperoxy-6-methylhept-4-en-2-yl]-4-hydroxy-7,12,16-trimethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid

Details

• Internal ID: 979234dd-73e9-4f8e-a913-c8bf949c8773
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-15-[(E,2R)-6-hydroperoxy-6-methylhept-4-en-2-yl]-4-hydroxy-7,12,16-trimethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• SMILES (Canonical): CC(CC=CC(C)(C)OO)C1CCC2(C1(CCC34C2CCC5C3(C4)C(CC(C5(C)C(=O)O)OC6C(C(C(CO6)O)O)O)O)C)C
• SMILES (Isomeric): C[C@H](C/C=C/C(C)(C)OO)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)[C@H](C[C@@H]([C@@]5(C)C(=O)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)C)C
• InChI: InChI=1S/C35H56O10/c1-19(8-7-12-30(2,3)45-42)20-11-13-32(5)22-9-10-23-33(6,29(40)41)25(44-28-27(39)26(38)21(36)17-43-28)16-24(37)35(23)18-34(22,35)15-14-31(20,32)4/h7,12,19-28,36-39,42H,8-11,13-18H2,1-6H3,(H,40,41)/b12-7+/t19-,20-,21-,22+,23+,24+,25+,26+,27-,28+,31-,32+,33+,34+,35-/m1/s1
• InChI Key: XEJAJKBDDYTJEO-YWCUOVOUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₁₀
• Molecular Weight: 636.80 g/mol
• Exact Mass: 636.38734798 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.14
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8131	81.31%
Caco-2	-	0.8545	85.45%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7117	71.17%
OATP2B1 inhibitior	-	0.7220	72.20%
OATP1B1 inhibitior	+	0.8333	83.33%
OATP1B3 inhibitior	+	0.9153	91.53%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	-	0.5106	51.06%
P-glycoprotein inhibitior	+	0.7129	71.29%
P-glycoprotein substrate	+	0.5792	57.92%
CYP3A4 substrate	+	0.7198	71.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	-	0.8590	85.90%
CYP2C9 inhibition	-	0.7261	72.61%
CYP2C19 inhibition	-	0.7834	78.34%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.7578	75.78%
CYP2C8 inhibition	+	0.6283	62.83%
CYP inhibitory promiscuity	-	0.9183	91.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6998	69.98%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9284	92.84%
Skin irritation	-	0.6375	63.75%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	+	0.5009	50.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.6764	67.64%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6668	66.68%
skin sensitisation	-	0.8586	85.86%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8485	84.85%
Acute Oral Toxicity (c)	III	0.3938	39.38%
Estrogen receptor binding	+	0.6930	69.30%
Androgen receptor binding	+	0.7280	72.80%
Thyroid receptor binding	-	0.5604	56.04%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.6926	69.26%
PPAR gamma	+	0.6354	63.54%
Honey bee toxicity	-	0.6984	69.84%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9772	97.72%

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	98.91%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	96.09%	85.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.05%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.46%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.83%	94.45%
CHEMBL240	Q12809	HERG	93.82%	89.76%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	92.08%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.92%	91.07%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	90.19%	97.47%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	89.89%	82.05%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.88%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.75%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.62%	93.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.47%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.33%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.28%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.97%	91.24%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.12%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.10%	92.62%
CHEMBL5028	O14672	ADAM10	83.97%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.85%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.74%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.40%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.15%	89.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.92%	92.88%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.84%	95.69%
CHEMBL2581	P07339	Cathepsin D	82.58%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.53%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.27%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.04%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.67%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.53%	95.56%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.27%	95.71%

Plants that contains it

• Markhamia lutea

Cross-Links

• PubChem: 163089346
• LOTUS: LTS0167733
• wikiData: Q105326372