Cucurbitacin E

Details

• Internal ID: edd4b325-6d2b-4f74-8cde-fa1328248cf5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-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=C4C3C=C(C(=O)C4(C)C)O)C)C)C)O)O
• SMILES (Isomeric): CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)C)O)O
• InChI: InChI=1S/C32H44O8/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/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
• InChI Key: NDYMQXYDSVBNLL-MUYMLXPFSA-N
• Popularity: 230 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₈
• Molecular Weight: 556.70 g/mol
• Exact Mass: 556.30361836 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 3.20

Synonyms

• 18444-66-1
• alpha-Elaterin
• alpha-Elaterine
• Cucurbitacine-E
• ELATERIN, ALPHA
• Cucurbitacine E
• .alpha.-Elaterin
• .alpha.-Elaterine
• NSC 106399
• NSC-106399
• UNII-V8A45XYI21
• CHEBI:3944
• V8A45XYI21
• [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
• EINECS 242-325-2
• NSC-521775
• 19-Norlanosta-1,5,23-triene-3,11,22-trione,25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9b,10a,16a,23E)-
• BRN 2343323
• 19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
• 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
• 25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione (9beta,10alpha,16alpha,23E)-
• CUE
• Cucurbitacin-E
• NSC106399
• 19-Nor-9.beta.,5,23-triene-3,11,22-trione, 2,16.alpha.,20,25-tetrahydroxy-9-methyl-, 25-acetate
• 19-Norlanosta-1,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
• 19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9beta,10alpha,16alpha,23E)-
• C32H44O8
• -Elaterin;-Elaterine
• CUCURBITACIN E [MI]
• (-)-CUCURBITACIN E
• SCHEMBL140616
• Cucurbitacin E (alpha-Elaterin)
• DTXSID601030496
• 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 2,16-alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
• 19-Nor-9beta,10alpha-lanosta-1,5,23-triene-3,11,22-trione, 2,16alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
• HY-N0417
• LMST01010107
• MFCD00135936
• NSC521775
• AKOS015896851
• C32-H44-O8
• CS-3817
• AC-34285
• AS-76174
• C08797
• A930353
• Q5192451
• (23E)-25-acetyloxy-2,16alpha,20-trihydroxy-9beta-methyl-19-nor-10alpha-lanosta-1,5,23-triene-3,11,22-trione
• (4R,23E)-2,16alpha,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate
• (9.BETA.,10.ALPHA.,16.ALPHA.,23E)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOSTA-1,5,23-TRIENE-3,11,22-TRIONE
• 19-Nor-9.beta.,10.alpha.-lanosta-1,5,23-triene-3,11,22-trione, 2,16.alpha.,20,25-tetrahydroxy-9-methyl-, 25-acetate
• 2,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-1,5,23-triene-3,11,22-trione 25-acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1803	P20701	Leukocyte adhesion glycoprotein LFA-1 alpha	180 nM	IC50	PMID: 7852999

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.39%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.86%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.79%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.55%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	92.81%	87.67%
CHEMBL1902	P62942	FK506-binding protein 1A	91.93%	97.05%
CHEMBL217	P14416	Dopamine D2 receptor	89.39%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.35%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.28%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.68%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.78%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	85.77%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.21%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.86%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.75%	97.25%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.88%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.71%	95.89%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.41%	96.39%

Plants that contains it

• Aglaia elliptica
• Bacopa monnieri
• Begonia nantoensis
• Bryonia alba
• Bryonia cretica
• Bryonia verrucosa
• Catananche caerulea
• Ceratosanthes hilariana
• Cirsium wallichii
• Citrullus lanatus
• Conobea scoparioides
• Corydalis calliantha
• Cucumis melo
• Cucumis sativus
• Cucurbita foetidissima
• Cucurbita maxima
• Cucurbita melopepo subsp. texana
• Ecballium elaterium
• Fritillaria cirrhosa
• Iberis amara
• Juglans regia
• Luffa aegyptiaca
• Luffa operculata
• Nernstia mexicana
• Phebalium whitei
• Quassia indica
• Rosa agrestis
• Rumex nepalensis
• Salvia urolepis
• Strychnos lucida
• Vitis betulifolia
• Wilbrandia ebracteata

Cross-Links

• PubChem: 5281319
• NPASS: NPC221144
• ChEMBL: CHEMBL455056
• LOTUS: LTS0271386
• wikiData: Q5192451