(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4-hydroxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]-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: 8b86ef26-42da-4b43-9aea-f715ffc1b68c
• 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)-4-hydroxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]-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(CCC=C(C)C)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](CCC=C(C)C)[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/C35H56O8/c1-19(2)8-7-9-20(3)21-12-13-32(5)23-10-11-24-33(6,30(40)41)26(43-29-28(39)27(38)22(36)17-42-29)16-25(37)35(24)18-34(23,35)15-14-31(21,32)4/h8,20-29,36-39H,7,9-18H2,1-6H3,(H,40,41)/t20-,21-,22-,23+,24+,25+,26+,27+,28-,29+,31-,32+,33+,34+,35-/m1/s1
• InChI Key: IMYPGBZBLDLUEO-SPYPWFITSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₈
• Molecular Weight: 604.80 g/mol
• Exact Mass: 604.39751874 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.67
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8984	89.84%
Caco-2	-	0.8363	83.63%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7871	78.71%
OATP2B1 inhibitior	-	0.5779	57.79%
OATP1B1 inhibitior	+	0.8282	82.82%
OATP1B3 inhibitior	+	0.9059	90.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	-	0.6521	65.21%
P-glycoprotein inhibitior	+	0.7302	73.02%
P-glycoprotein substrate	+	0.5052	50.52%
CYP3A4 substrate	+	0.7088	70.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.9067	90.67%
CYP2C9 inhibition	-	0.5688	56.88%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	-	0.7697	76.97%
CYP2C8 inhibition	+	0.5255	52.55%
CYP inhibitory promiscuity	-	0.8929	89.29%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7159	71.59%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.5454	54.54%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.6115	61.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.7762	77.62%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6684	66.84%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7949	79.49%
Acute Oral Toxicity (c)	I	0.4325	43.25%
Estrogen receptor binding	+	0.7022	70.22%
Androgen receptor binding	+	0.7440	74.40%
Thyroid receptor binding	-	0.5731	57.31%
Glucocorticoid receptor binding	+	0.6188	61.88%
Aromatase binding	+	0.6688	66.88%
PPAR gamma	+	0.6259	62.59%
Honey bee toxicity	-	0.7214	72.14%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.9803	98.03%

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	97.11%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.22%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.46%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.96%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.89%	93.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.55%	89.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.92%	91.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.91%	92.62%
CHEMBL2581	P07339	Cathepsin D	87.57%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.39%	96.61%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.61%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.55%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.38%	96.38%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.21%	95.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.54%	82.50%
CHEMBL284	P27487	Dipeptidyl peptidase IV	85.03%	95.69%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.32%	85.31%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.92%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.31%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.90%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.74%	98.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.70%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.65%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.36%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.13%	96.47%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.00%	95.17%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.28%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.45%	96.95%

Plants that contains it

• Combretum molle

Cross-Links

• PubChem: 14189862
• LOTUS: LTS0020452
• wikiData: Q105116008