Cucurbitacin D

Details

• Internal ID: c55db9ff-f4cf-4517-bd6f-12e44bddbf7d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2CC(C1=O)O)C)C)C(C)(C(=O)C=CC(C)(C)O)O)O)C)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O
• InChI: InChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1
• InChI Key: SRPHMISUTWFFKJ-QJNWWGCFSA-N
• Popularity: 70 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₇
• Molecular Weight: 516.70 g/mol
• Exact Mass: 516.30870374 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.10

Synonyms

• 3877-86-9
• Elatericin A
• Elatericine A
• 5I62H4ORC7
• CHEBI:3943
• NSC-308606
• NSC-521776
• DTXSID401032034
• (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• 19-Norlanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)-
• (2S,8S,9R,10R,13R,14S,16R,17R)-17-((E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta(a)phenanthrene-3,11-dione
• RefChem:579529
• DTXCID501517035
• Cucurbitacine (D)
• 19-Norlanosta-5,23-diene-3,11,22-trione,2,16,20,25-tetrahydroxy-9-methyl-, (2b,9b,10a,16a,23E)-
• NSC308606
• CucurbitacinD
• NSC 308606
• NSC 521776
• UNII-5I62H4ORC7
• 19-nor-9.beta.,23-diene-3,11,22-trione, 9-methyl-2.beta.,16.alpha.,20,25-tetrahydroxy-
• 19-Norlanosta-5,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23E)-
• CUCURBITACINE D
• SCHEMBL230654
• Cucurbitacin D (Elatericin A)
• CHEMBL493646
• orb1684984
• HY-N1986
• LMST01010106
• MFCD01711333
• NSC521776
• AKOS015896755
• FC73908
• NCGC00385253-01
• 19-Nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-
• 19-Norlanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23E)-
• AS-79683
• DA-62532
• CS-0018307
• NS00094066
• C08796
• Q15410915
• (23E)-2beta,16alpha,20,25-tetrahydroxy-10alpha-cucurbita-5,23-diene-3,11,22-trione
• (23E)-2beta,16alpha,20,25- tetrahydroxy-9beta-methyl-19-nor-10alpha-lanosta-5,23-diene-3,11,22-trione
• (2S,4R,23E)-2,16,20,25-tetrahydroxy-9beta,10,14-trimethyl-4,9-cyclo-9,10-seco-16alpha-cholesta-5,23-diene-1,11,22-trione
• (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,1R)-1,5-dihydroxy-1,5-dimethyl-2-oxo-hex-3-enyl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• (2ss,9ss,10a,16a,23E)-2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione; Cucurbitacine D; Elatericin A
• NCGC00385253-01_C30H44O7_(2S,4R,9beta,16alpha,23E)-2,16,20,25-Tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-5,23-diene-1,11,22-trione

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	1360 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	95.85%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.43%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.57%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.40%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.12%	87.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.15%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	84.91%	97.05%
CHEMBL221	P23219	Cyclooxygenase-1	84.41%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.37%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	84.03%	91.19%
CHEMBL4208	P20618	Proteasome component C5	83.72%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.70%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.54%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.45%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.00%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.34%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.30%	99.23%

Plants that contains it

• Acanthosicyos horridus
• Begonia heracleifolia
• Begonia parviflora
• Bryonia cretica
• Bryonia verrucosa
• Cogniauxia podolaena
• Cucurbita foetidissima
• Cucurbita melopepo subsp. texana
• Cucurbita pepo
• Ecballium elaterium
• Elaeocarpus chinensis
• Elaeocarpus hainanensis
• Elaeocarpus mastersii
• Gonystylus keithii
• Gurania subumbellata
• Helicteres angustifolia
• Iberis umbellata
• Luffa operculata
• Neoalsomitra clavigera
• Physocarpus opulifolius
• Sloanea zuliaensis
• Trichosanthes bracteata
• Trichosanthes kirilowii
• Trichosanthes miyagii
• Trichosanthes rosthornii
• Trichosanthes tricuspidata
• Wilbrandia ebracteata

Cross-Links

• PubChem: 5281318
• NPASS: NPC311612
• ChEMBL: CHEMBL493646
• LOTUS: LTS0059270
• wikiData: Q15410915