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C4493

Sigma-Aldrich

Cucurbitacin I hydrate

≥95% (HPLC), solid

Synonym(s):

2,16α,20,25-Tetrahydroxy-9-methyl-19-Nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione, Elatericin B, JSI-124, NSC 521777

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About This Item

Empirical Formula (Hill Notation):
C30H42O7 · xH2O
CAS Number:
2222-07-3
Molecular Weight:
514.65 (anhydrous basis)
EC Number:
218-736-8
UNSPSC Code:
12352200
PubChem Substance ID:
329775065
NACRES:
NA.77

Assay

≥95% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

O.CC(C)(O)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

InChI

1S/C30H42O7.H2O/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;1H2/b12-11+;/t17-,19-,20+,23+,27+,28-,29+,30+;/m1./s1

InChI key

ZKDSPEWKSJCXQE-NEBRQAMTSA-N

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.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the JAKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Abdullah Mahmud et al.
Biomacromolecules, 10(3), 471-478 (2009-01-30)
An increase in the degree of chemical compatibility between drug and polymeric structure in the core has been shown to raise the encapsulation efficiency and lower the rate of drug release from polymeric micelles. In this study, to achieve an
Yi-Wei Chen et al.
Molecular cancer therapeutics, 9(11), 2879-2892 (2010-11-11)
Head and neck squamous cell carcinoma (HNSCC) is a prevalent cancer worldwide. Signal transducers and activators of transcription 3 (STAT3) signaling is reported to promote tumor malignancy and recurrence in HNSCC. Cucurbitacins, triterpenoid derivatives, are strong STAT3 inhibitors with anticancer
Han-Shui Hsu et al.
Cancer, 117(13), 2970-2985 (2011-01-13)
Signal transducer and activator of transcription 3 (STAT3) signaling reportedly promotes tumor malignancy and recurrence in nonsmall cell lung cancer (NSCLC). It was demonstrated previously that the STAT3 pathway maintains the tumorigenicity and therapeutic resistance of malignant tumors as well
Vivian W Y Lui et al.
Carcinogenesis, 30(12), 2085-2094 (2009-10-22)
Nasopharyngeal carcinoma (NPC) is an Asian-prevalent head and neck cancer with high invasiveness. Although several important risk factors for NPC development have been identified, there is currently no preventive strategy for NPC, even in endemic regions. Signal transducer and activator
Ommoleila Molavi et al.
Molecular pharmaceutics, 7(2), 364-374 (2009-12-25)
Constitutively activated signal transducer and activator of transcription-3 (STAT3) in tumor and dendritic cells (DCs) plays a critical role in tumor-induced immunosuppression. This is considered a major challenge in effective immunotherapy of cancer. Herein we describe the development of a
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