| Identification | Back Directory | [Name]
CUCURBITACIN I | [CAS]
2222-07-3 | [Synonyms]
JSI-124
Ibamarin
ELATERIN B
NSC 521777
ELATERICIN B
CUCURBITACIN I
5-tetrahydroxy-
cucurbitacine(i)
CUCURBITACIN I(SH)
CUCURBITACIN I hplc
1,2-dehydroelatericina
CUCURBITACIN I WITH HPLC
Cucurbitacin I hydrate
Cucurbitacin I (JSI-124)
calebassine/cucurbitacin
Cucurbitacin I (Elatericin B
19-nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione,9-methyl-2,16,20,2
2,16a,20,25-Tetrahydroxy-9b-methyl-10a-19-norlanosta-1,5,23(E)-triene-3,11,22-trione
2,16α,20,25-tetrahydroxy-9β-methyl-10α-19-norlanosta-1,5,23(E)-triene-3,11,22-trione
2,16α,20,25-tetrahydroxy-9-methyl-19-Nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione
(9β,10α,23E)-2,16α,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
(9β,10α,16α,23E)-2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
2,16alpha,20,25-tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione
19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9b,10a,16a,23E)-
19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9β,10α,16α,23E)-
Elatericin B, JSI-124, NSC 521777, 2,16α,20,25-Tetrahydroxy-9-methyl-19-Nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione | [EINECS(EC#)]
218-736-8 | [Molecular Formula]
C30H42O7 | [MDL Number]
MFCD00075712 | [MOL File]
2222-07-3.mol | [Molecular Weight]
514.65 |
| Chemical Properties | Back Directory | [Melting point ]
148-150°C | [Boiling point ]
698.3±55.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
≥22.45 mg/mL in DMSO; insoluble in EtOH; ≥51.2 mg/mL in H2O with ultrasonic | [form ]
solid | [pka]
8.51±0.70(Predicted) | [color ]
white to off-white | [InChIKey]
NISPVUDLMHQFRQ-KUIOOTTBNA-N | [SMILES]
[C@@]12(C)CC(O)C(C(O)(C)C(=O)/C=C/C(O)(C)C)[C@@]1(C)CC(=O)[C@]1(C)C3C=C(C(=O)C(C)(C)C3=CC[C@@]21[H])O |&1:0,17,22,35,r| | [LogP]
2.330 (est) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T+ | [Risk Statements ]
25-28 | [Safety Statements ]
1-22-45-36/37-28 | [RIDADR ]
UN 2811 6.1/PG 1 | [WGK Germany ]
3 | [RTECS ]
RC6200000 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 1 Oral | [Toxicity]
LD50 oral in mouse: 5mg/kg |
| Hazard Information | Back Directory | [Description]
Cucurbitacin I is a naturally occurring tetracyclic triterpenoid compound with a variety of physiological effects, including induction of apoptosis and blockade of cell cycle progression in various cancer cells. It has also been shown to have anti-angiogenic activity. Cucurbitacin I inhibits the phosphorylation of vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1, which are key regulators of endothelial cell function and angiogenesis. Therefore, Cucurbitacin I is considered a potential angiogenesis inhibitor candidate for cancer therapy[1]. | [Uses]
Cucurbitacin I can be useful in the study of edible vitalmelon fruit extract and adipogenesis. | [Definition]
ChEBI: A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22. | [Biological Activity]
Selective inhibitor of STAT3/JAK2 signaling. Inhibits the activation of STAT3 and JAK2 and displays no activity on Src, Akt, ERK and JNK. Suppresses phosphotyrosine levels of STAT3, inhibits STAT3 DNA binding and STAT3-mediated gene expression. Induces apoptosis in cell lines expressing constitutively active tyrosine-phosphorylated STAT3. | [Biochem/physiol Actions]
Cucurbitacin I (JSI-124) is a novel selective inhibitor of the janus kinase 2/signal transducer and activator of transcription 3 (JAK2/STAT3) signaling pathway with anti-proliferative and anti-tumor properties. | [storage]
Store at -20°C | [References]
blaskovich ma, sun j, cantor a et al. discovery of jsi-124 (cucurbitacin i), a selective janus kinase/signal transducer and activator of transcription 3 signaling pathway inhibitor with potent antitumor activity against human and murine cancer cells in mice.cancer res. 2003 mar 15;63(6):1270-9.yu h, lee h, herrmann a et al. revisiting stat3 signalling in cancer: new and unexpected biological functions.nat rev cancer. 2014 nov;14(11):736-46. doi: 10.1038/nrc3818.song j, liu h, li z et al. cucurbitacin i inhibits cell migration and invasion and enhances chemosensitivity in colon cancer. oncol rep. 2015 apr;33(4):1867-71. qi j, xia g, huang cr et al. jsi-124 (cucurbitacin i) inhibits tumor angiogenesis of human breast cancer through reduction of stat3 phosphorylation. am j chin med. 2015;43(2):337-47.kim hj, kim jk et al. antiangiogenic effects of cucurbitacin-i. arch pharm res. 2015 feb;38(2):290-8. yuan g, yan sf, xue h et al. cucurbitacin i induces protective autophagy in glioblastoma in vitro and in vivo. j biol chem. 2014 apr 11;289(15):10607-19. |
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