| 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 |
| CAS Number: | 2222-07-3 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 218-736-8 |
| FDA UNII: | SHQ47990PH |
| Nikkaji Web: | J7.369E |
| MDL: | MFCD09971044 |
| XlogP3-AA: | 2.70 (est) |
| Molecular Weight: | 514.65914000 |
| Formula: | C30 H42 O7 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 698.30 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 734.00 °F. TCC ( 390.10 °C. ) (est)
|
| logP (o/w): | 2.330 (est) |
| Soluble in: |
| | water, 5.488 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-mouse LD50 5 mg/kg
Chimica Therapeutica. Vol. 4, Pg. 459, 1969.
|
| Dermal Toxicity: |
|
Not determined
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for cucurbitacin I usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for cucurbitacin I flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281321 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (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 |
| Chemidplus:0002222073 |
| RTECS:RC6200000 for cas# 2222-07-3 |
References:
| | (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 |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281321 |
| Pubchem (sid): | 135032833 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | cucurbitacine (I) | | 1,2- | dehydroelatericin A | | (8S,9R,10R,13R,14S,16R,17R)-17-[(2R,4E)-2,6- | dihydroxy-6-methyl-3-oxo-4-hepten-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3,11(4H)-dione | | (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 | | | elatericin B | | 19-nor | lanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)- (VAN) (9CI) | | 19-nor-9-beta,10-alpha- | lanosta-1,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy- | | 2,16alpha,20,25- | tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione |
Articles:
| PubMed:Transcriptional profiling of GBM invasion genes identifies effective inhibitors of the LIM kinase-Cofilin pathway. |
| PubMed:N-myc downstream-regulated gene 2 (NDRG2) suppresses the epithelial-mesenchymal transition (EMT) in breast cancer cells via STAT3/Snail signaling. |
| PubMed:Downregulation of endogenous STAT3 augments tumoricidal activity of interleukin 15 activated dendritic cell against lymphoma and leukemia via TRAIL. |
| PubMed:Nanoprecipitation is more efficient than emulsion solvent evaporation method to encapsulate cucurbitacin I in PLGA nanoparticles. |
| PubMed:JSI124 inhibits breast cancer cell growth by suppressing the function of B cells via the downregulation of signal transducer and activator of transcription 3. |
| PubMed:Cucurbitacin-I, a natural cell-permeable triterpenoid isolated from Cucurbitaceae, exerts potent anticancer effect in colon cancer. |
| PubMed:Antiangiogenic effects of cucurbitacin-I. |
| PubMed:Cucurbitacin I induces protective autophagy in glioblastoma in vitro and in vivo. |
| PubMed:Dendritic cells loaded with myeloma cells pretreated with a combination of JSI-124 and bortezomib generate potent myeloma-specific cytotoxic T lymphocytes in vitro. |
| PubMed:Cucurbitacin B and cucurbitacin I suppress adipocyte differentiation through inhibition of STAT3 signaling. |
| PubMed:Cucurbitacin I blocks cerebrospinal fluid and platelet derived growth factor-BB stimulation of leptomeningeal and meningioma DNA synthesis. |
| PubMed:Polyunsaturated fatty acids promote the expansion of myeloid-derived suppressor cells by activating the JAK/STAT3 pathway. |
| PubMed:Chrysin overcomes TRAIL resistance of cancer cells through Mcl-1 downregulation by inhibiting STAT3 phosphorylation. |
| PubMed:Membrane-bound interleukin-21 and CD137 ligand induce functional human natural killer cells from peripheral blood mononuclear cells through STAT-3 activation. |
| PubMed:Cucurbitacin I inhibits Rac1 activation in breast cancer cells by a reactive oxygen species-mediated mechanism and independently of Janus tyrosine kinase 2 and P-Rex1. |
| PubMed:Activation of the NF-κB pathway by the STAT3 inhibitor JSI-124 in human glioblastoma cells. |
| PubMed:On-target JAK2/STAT3 inhibition slows disease progression in orthotopic xenografts of human glioblastoma brain tumor stem cells. |
| PubMed:The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver. |
| PubMed:Inhibition of the Jak-STAT pathway prevents CNTF-mediated survival of axotomized oxytocinergic magnocellular neurons in organotypic cultures of the rat supraoptic nucleus. |
| PubMed:Janus kinase 2 and signal transducer and activator of transcription 3 activation is not essential for CCL3-, CCL5- or CCL8-induced chemotaxis. |
| PubMed:Direct regulation of the proglucagon gene by insulin, leptin, and cAMP in embryonic versus adult hypothalamic neurons. |
| PubMed:Cucurbitacin induces autophagy through mitochondrial ROS production which counteracts to limit caspase-dependent apoptosis. |
| PubMed:Signal transducer and activator of transcription-5 mediates neuronal apoptosis induced by inhibition of Rac GTPase activity. |
| PubMed:Targeting signal transducer and activator of transcription 3 pathway by cucurbitacin I diminishes self-renewing and radiochemoresistant abilities in thyroid cancer-derived CD133+ cells. |
| PubMed:IL-6 stimulates STAT3 and Pim-1 kinase in pancreatic cancer cell lines. |
| PubMed:Inhibition of phosphorylated STAT3 by cucurbitacin I enhances chemoradiosensitivity in medulloblastoma-derived cancer stem cells. |
| PubMed:In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma. |
| PubMed:High glucose-induced expression of inflammatory cytokines and reactive oxygen species in cultured astrocytes. |
| PubMed:Cucurbitane glucosides from the root of Machilus yaoshansis. |
| PubMed:Glioblastoma-induced inhibition of Langerhans cell differentiation from CD34(+) precursors is mediated by IL-6 but unaffected by JAK2/STAT3 inhibition. |
| PubMed:Cucurbitacin-I (JSI-124) activates the JNK/c-Jun signaling pathway independent of apoptosis and cell cycle arrest in B leukemic cells. |
| PubMed:Cucurbitacin I inhibits tumorigenic ability and enhances radiochemosensitivity in nonsmall cell lung cancer-derived CD133-positive cells. |
| PubMed:Inhibition of constitutive activation of STAT3 by curcurbitacin-I (JSI-124) sensitized human B-leukemia cells to apoptosis. |
| PubMed:Cucurbitacin I inhibits cell motility by indirectly interfering with actin dynamics. |
| PubMed:Cucurbitacin I suppressed stem-like property and enhanced radiation-induced apoptosis in head and neck squamous carcinoma--derived CD44(+)ALDH1(+) cells. |
| PubMed:STAT3alpha is oncogenic for endometrial carcinoma cells and mediates the oncogenic effects of autocrine human growth hormone. |
| PubMed:Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells. |
| PubMed:The neurofibromatosis type 1 tumor suppressor controls cell growth by regulating signal transducer and activator of transcription-3 activity in vitro and in vivo. |
| PubMed:Development of a poly(d,l-lactic-co-glycolic acid) nanoparticle formulation of STAT3 inhibitor JSI-124: implication for cancer immunotherapy. |
| PubMed:Screening a panel of drugs with diverse mechanisms of action yields potential therapeutic agents against neuroblastoma. |
| PubMed:Cucurbitacin I elicits anoikis sensitization, inhibits cellular invasion and in vivo tumor formation ability of nasopharyngeal carcinoma cells. |
| PubMed:Prediction of the solubility of cucurbitacin drugs in self-associating poly(ethylene oxide)-b-poly(alpha-benzyl carboxylate epsilon-caprolactone) block copolymer with different tacticities using molecular dynamics simulation. |
| PubMed:Stability of cucurbitacin E in human plasma: chemical hydrolysis and role of plasma esterases. |
| PubMed:Roles of nonpolar and polar intermolecular interactions in the improvement of the drug loading capacity of PEO-b-PCL with increasing PCL content for two hydrophobic Cucurbitacin drugs. |
| PubMed:Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands. |
| PubMed:IL-6-induced activation of MYC is responsible for the down-regulation of CD33 expression in CD33+ myeloma cells. |
| PubMed:Quantitative determination of cucurbitacin E and cucurbitacin I in homoeopathic mother tincture of Gratiola officinalis L. by HPLC. |
| PubMed:Self-associating poly(ethylene oxide)-b-poly(alpha-cholesteryl carboxylate-epsilon-caprolactone) block copolymer for the solubilization of STAT-3 inhibitor cucurbitacin I. |
| PubMed:Curcuminoid-phospholipid complex induces apoptosis in mammary epithelial cells by STAT-3 signaling. |
| PubMed:Development of a STAT3 reporter prostate cancer cell line for high throughput screening of STAT3 activators and inhibitors. |
| PubMed:Immunomodulatory and anticancer effects of intra-tumoral co-delivery of synthetic lipid A adjuvant and STAT3 inhibitor, JSI-124. |
| PubMed:Activated kRas protects colon cancer cells from cucurbitacin-induced apoptosis: the role of p53 and p21. |
| PubMed:JSI-124 inhibits glioblastoma multiforme cell proliferation through G(2)/M cell cycle arrest and apoptosis augment. |
| PubMed:Green tea polyphenol epigallocatechin-3-gallate suppresses collagen production and proliferation in keloid fibroblasts via inhibition of the STAT3-signaling pathway. |
| PubMed:Synergistic antitumor effects of CpG oligodeoxynucleotide and STAT3 inhibitory agent JSI-124 in a mouse melanoma tumor model. |
| PubMed:Essential role for Stat5 in the neurotrophic but not in the neuroprotective effect of erythropoietin. |
| PubMed:Inhibition of STAT3 promotes the efficacy of adoptive transfer therapy using type-1 CTLs by modulation of the immunological microenvironment in a murine intracranial glioma. |
| PubMed:Cucurbitacin I inhibits Stat3 and induces apoptosis in Sézary cells. |
| PubMed:STAT3-dependent mouse embryonic stem cell differentiation into cardiomyocytes: analysis of molecular signaling and therapeutic efficacy of cardiomyocyte precommitted mES transplantation in a mouse model of myocardial infarction. |
| PubMed:Polymeric micelles for the solubilization and delivery of STAT3 inhibitor cucurbitacins in solid tumors. |
| PubMed:Role of signal transducer and activator of transcription-3 in estradiol-mediated neuroprotection. |
| PubMed:Two novel glycosidic triterpene alkaloids from the stem barks of Machilus yaoshansis. |
| PubMed:Effect of cucurbitacins on bilirubin-albumin binding in human plasma. |
| PubMed:Development of a sensitive and specific liquid chromatography/mass spectrometry method for the quantification of cucurbitacin I (JSI-124) in rat plasma. |
| PubMed:JSI-124 (cucurbitacin I) inhibits Janus kinase-3/signal transducer and activator of transcription-3 signalling, downregulates nucleophosmin-anaplastic lymphoma kinase (ALK), and induces apoptosis in ALK-positive anaplastic large cell lymphoma cells. |
| PubMed:P2 purinergic receptors signal to STAT3 in astrocytes: Difference in STAT3 responses to P2Y and P2X receptor activation. |
| PubMed:Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. |
| PubMed:STAT3-independent inhibition of lysophosphatidic acid-mediated upregulation of connective tissue growth factor (CTGF) by cucurbitacin I. |
| PubMed:Stat3 contributes to keloid pathogenesis via promoting collagen production, cell proliferation and migration. |
| PubMed:[Relationships of Aulacophora beetles feeding behavior with cucurbitacin types in host crops]. |
| PubMed:Regulation of dendritic cell differentiation and antitumor immune response in cancer by pharmacologic-selective inhibition of the janus-activated kinase 2/signal transducers and activators of transcription 3 pathway. |
| PubMed:Targeting Stat3 in cancer therapy. |
| PubMed:Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. |
| PubMed: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. |
| PubMed:Effect of cucurbitacins on mRNA coding for laccase in Botrytis cinerea. |
| PubMed:Oviposition stimulants and deterrents regulating differential acceptance ofIberis amara byPieris rapae andP. napi oleracea. |
| PubMed:A new cucurbitacin profile forCucurbita andreana: A candidate for cucurbitacin tissue culture. |
| PubMed:Inhibition of the biosynthesis of deoxyribonucleic acid, ribonucleic acid and protein in HeLa S3 cells by cucurbitacins, glucocorticoid-like cytotoxic triterpenes. |
| PubMed:[Poisoning with a kind of Bitter Edible Gourd]. |
| PubMed:Binding of the cytotoxic and antitumor triterpenes, cucurbitacins, to glucocorticoid receptors of HeLa cells. |
|
