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2222-07-3

2222-07-3 Structure

2222-07-3 Structure
IdentificationBack 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 PropertiesBack 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
[LogP]

2.330 (est)
Safety DataBack 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
[Toxicity]

LD50 oral in mouse: 5mg/kg
Hazard InformationBack Directory
[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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