(3S,8S,9R,10R,13R,14S,17R)-3-hydroxy-17-[(2R,5R)-6-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

Details

• Internal ID: 9853f512-1f4e-40d3-85c1-c354f5410832
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (3S,8S,9R,10R,13R,14S,17R)-3-hydroxy-17-[(2R,5R)-6-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC(CCC(C(C)(C)O)OC1C(C(C(C(O1)CO)O)O)O)C2CCC3(C2(CC(=O)C4(C3CC=C5C4CCC(C5(C)C)O)C)C)C
• SMILES (Isomeric): C[C@H](CC[C@H](C(C)(C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)[C@H]2CC[C@@]3([C@@]2(CC(=O)[C@@]4([C@H]3CC=C5[C@H]4CC[C@@H](C5(C)C)O)C)C)C
• InChI: InChI=1S/C36H60O9/c1-19(9-14-27(33(4,5)43)45-31-30(42)29(41)28(40)23(18-37)44-31)20-15-16-34(6)24-12-10-21-22(11-13-25(38)32(21,2)3)36(24,8)26(39)17-35(20,34)7/h10,19-20,22-25,27-31,37-38,40-43H,9,11-18H2,1-8H3/t19-,20-,22-,23-,24+,25+,27-,28-,29+,30-,31+,34+,35-,36+/m1/s1
• InChI Key: FEFDBUMZKFXMGF-AFMKTRLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₀O₉
• Molecular Weight: 636.90 g/mol
• Exact Mass: 636.42373349 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.50
• 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	+	0.9026	90.26%
Caco-2	-	0.8309	83.09%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.7226	72.26%
OATP1B1 inhibitior	+	0.8554	85.54%
OATP1B3 inhibitior	-	0.2724	27.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6568	65.68%
BSEP inhibitior	-	0.6495	64.95%
P-glycoprotein inhibitior	+	0.7277	72.77%
P-glycoprotein substrate	-	0.5465	54.65%
CYP3A4 substrate	+	0.7188	71.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8687	86.87%
CYP3A4 inhibition	-	0.8752	87.52%
CYP2C9 inhibition	-	0.8084	80.84%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8266	82.66%
CYP2C8 inhibition	+	0.4878	48.78%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9263	92.63%
Skin irritation	+	0.5185	51.85%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.7637	76.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7619	76.19%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5808	58.08%
skin sensitisation	-	0.9059	90.59%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6193	61.93%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.6040	60.40%
Androgen receptor binding	+	0.7443	74.43%
Thyroid receptor binding	-	0.5570	55.70%
Glucocorticoid receptor binding	+	0.6374	63.74%
Aromatase binding	+	0.6445	64.45%
PPAR gamma	+	0.6012	60.12%
Honey bee toxicity	-	0.7575	75.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.95%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.04%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.74%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.69%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.85%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	89.70%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.20%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.01%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.81%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.74%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.31%	96.21%
CHEMBL4040	P28482	MAP kinase ERK2	85.40%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.36%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	84.46%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	84.27%	94.45%
CHEMBL1907	P15144	Aminopeptidase N	84.16%	93.31%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.94%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.51%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.36%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.49%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.26%	93.04%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.72%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.49%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.82%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.40%	91.07%
CHEMBL4581	P52732	Kinesin-like protein 1	80.34%	93.18%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.26%	99.23%
CHEMBL5028	O14672	ADAM10	80.17%	97.50%

Plants that contains it

• Siraitia grosvenorii

Cross-Links

• PubChem: 11093434
• LOTUS: LTS0208315
• wikiData: Q104993944