Cucurbitacin I

Details

• Internal ID: b61f9d24-95d5-457e-b57d-2bd3d7dbea90
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
• IUPAC Name: (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-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(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(C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C/C(C)(C)O)O)O
• InChI: InChI=1S/C30H42O7/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/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1
• InChI Key: NISPVUDLMHQFRQ-MKIKIEMVSA-N
• Popularity: 131 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₇
• Molecular Weight: 514.60 g/mol
• Exact Mass: 514.29305367 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.70

Synonyms

• 2222-07-3
• Elatericin B
• Cucurbitacine (I)
• JSI-124
• 1,2-Dehydroelatericin A
• NSC-521777
• CHEBI:3947
• SHQ47990PH
• EINECS 218-736-8
• NSC 112167
• NSC 521777
• NSC-112167
• (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-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• NSC521777
• 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-
• 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-
• 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)-
• 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)- (VAN)
• 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione
• MLS002702902
• 19-nor-9.beta.,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-
• JSI 124
• DTXSID501015546
• Elatericin B;JSI-124;NSC-521777
• 19-Norlanosta-1,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.)- (VA
• CUCURBITACCINE (I)
• UNII-SHQ47990PH
• NSC-521777Elatericin B
• Cucurbitacin I (Elatericin B)
• CHEMBL387737
• SCHEMBL2523066
• SCHEMBL15914446
• HY-N1405
• LMST01010110
• NSC112167
• AKOS024456675
• CS-5431
• NCGC00388208-02
• 28580-39-4
• LS-97302
• MS-29560
• XT170627
• Elatericin B; JSI-124; NSC-521777
• C08800
• F85354
• Q27106265
• (4R,9beta,16alpha,23E)-2,16,20,25-tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene-1,11,22-trione
• (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-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• (9?,10?,16?,23E)-2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
• 2,16,20,25-Terahydroxycucurbita-1,5,23-triene-3,11,22-trione - Iberis umbellata (candytuft)

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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	794.3 nM	Potency	via Super-PRED
CHEMBL1803	P20701	Leukocyte adhesion glycoprotein LFA-1 alpha	950 nM	IC50	PMID: 7852999
CHEMBL1293232	Q16637	Survival motor neuron protein	354.8 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	97.30%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	93.66%	87.67%
CHEMBL2581	P07339	Cathepsin D	92.18%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.76%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	90.60%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.18%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.01%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.81%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	87.17%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.29%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.39%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.98%	91.07%
CHEMBL4208	P20618	Proteasome component C5	80.68%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.41%	91.19%

Plants that contains it

• Begonia nantoensis
• Bryonia alba
• Bryonia verrucosa
• Citrullus colocynthis
• Cucumis sativus
• Cucurbita melopepo subsp. texana
• Cucurbita pepo
• Ecballium elaterium
• Elaeocarpus chinensis
• Elaeocarpus hainanensis
• Gyrinops walla
• Hemsleya endecaphylla
• Iberis amara

Cross-Links

• PubChem: 5281321
• NPASS: NPC111323
• ChEMBL: CHEMBL387737
• LOTUS: LTS0230723
• wikiData: Q27106265