[(E,6R)-6-[(2S,9R,10R,13R,14S,16R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate

Details

• Internal ID: 3dd5e61a-73d1-4e76-89a6-dc24079a7a2e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: [(E,6R)-6-[(2S,9R,10R,13R,14S,16R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
• SMILES (Canonical): CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O
• SMILES (Isomeric): CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)(C1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3(C2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O
• InChI: InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22?,25?,29+,30-,31+,32+/m1/s1
• InChI Key: IXQKXEUSCPEQRD-KQONOONZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₆O₈
• Molecular Weight: 558.70 g/mol
• Exact Mass: 558.31926842 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	-	0.7257	72.57%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7731	77.31%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.8366	83.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8995	89.95%
P-glycoprotein inhibitior	+	0.7181	71.81%
P-glycoprotein substrate	-	0.5278	52.78%
CYP3A4 substrate	+	0.7107	71.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9083	90.83%
CYP3A4 inhibition	-	0.7135	71.35%
CYP2C9 inhibition	-	0.8849	88.49%
CYP2C19 inhibition	-	0.9079	90.79%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.8531	85.31%
CYP2C8 inhibition	+	0.5735	57.35%
CYP inhibitory promiscuity	-	0.8940	89.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5810	58.10%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9136	91.36%
Skin irritation	+	0.6111	61.11%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5350	53.50%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7520	75.20%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.4688	46.88%
Acute Oral Toxicity (c)	I	0.7875	78.75%
Estrogen receptor binding	+	0.7155	71.55%
Androgen receptor binding	+	0.7436	74.36%
Thyroid receptor binding	+	0.6335	63.35%
Glucocorticoid receptor binding	+	0.7897	78.97%
Aromatase binding	+	0.7551	75.51%
PPAR gamma	+	0.6025	60.25%
Honey bee toxicity	-	0.6695	66.95%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	270 nM	IC50	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	316.2 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	199.5 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.58%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.02%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.69%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.15%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	90.42%	97.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.54%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.76%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.79%	89.34%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.55%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.47%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.37%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.64%	82.69%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.16%	97.21%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.07%	91.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.89%	99.23%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.77%	96.39%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.32%	89.00%

Plants that contains it

• Bryonia alba
• Citrullus colocynthis
• Cucumis melo
• Ecballium elaterium
• Hemsleya graciliflora
• Luffa aegyptiaca
• Trichosanthes kirilowii

Cross-Links

• PubChem: 25245488
• NPASS: NPC15598