| Name: | (2S,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-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| CAS Number: | 3877-86-9 |  3D/inchi
|
| FDA UNII: | 5I62H4ORC7 |
| Nikkaji Web: | J8.271F |
| MDL: | MFCD01711333 |
| XlogP3-AA: | 2.10 (est) |
| Molecular Weight: | 516.67508000 |
| Formula: | C30 H44 O7 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:pharmaceuticals / chemical synthisis
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 684.00 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 719.00 °F. TCC ( 381.40 °C. ) (est)
|
| logP (o/w): | 1.480 (est) |
| Soluble in: |
| | water, 5.08 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| |
| 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: |
intravenous-cat LD50 900 ug/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
intravenous-dog LD50 1000 ug/kg
GASTROINTESTINAL: NAUSEA OR VOMITING
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
intraperitoneal-mouse LD50 1750 ug/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
intravenous-mouse LD50 960 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
oral-mouse LD50 5 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chimica Therapeutica. Vol. 4, Pg. 459, 1969.
intraperitoneal-rat LD50 1300 ug/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
oral-rat LD50 8200 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
|
| Dermal Toxicity: |
subcutaneous-mouse LD50 4600 ug/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
subcutaneous-rat LD50 3400 ug/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 315, 1961.
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| Category: | | pharmaceuticals / chemical synthisis |
| Recommendation for cucurbitacin D usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for cucurbitacin D 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 :5281318 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2S,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-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| Chemidplus:0003877869 |
References:
| | (2S,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-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281318 |
| Pubchem (sid): | 135174996 |
| Pherobase: | View |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | cucurbitacine (D) | | (2S,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-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione | | | elatericin A | | | elatericine A | | 19-nor | lanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)- (9CI) | | 19-nor-9-beta,10-alpha- | lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy- |
Articles:
| PubMed:Cucurbitacin-D-induced CDK1 mRNA up-regulation causes proliferation arrest of a non-small cell lung carcinoma cell line (NSCLC-N6). |
| PubMed:Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene. |
| PubMed:Trichosanthes kirilowii Ethanol Extract and Cucurbitacin D Inhibit Cell Growth and Induce Apoptosis through Inhibition of STAT3 Activity in Breast Cancer Cells. |
| PubMed:Cucurbitacin D is a new inflammasome activator in macrophages. |
| PubMed:Natural compounds as potential treatments of NF2-deficient schwannoma and meningioma: cucurbitacin D and goyazensolide. |
| 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:Cucurbitacin D induces growth inhibition, cell cycle arrest, and apoptosis in human endometrial and ovarian cancer cells. |
| PubMed:[Studies on chemical constituents in roots of Helicteres angustifolia]. |
| PubMed:Apoptosis induction through proteasome inhibitory activity of cucurbitacin D in human T-cell leukemia. |
| PubMed:Cucurbitacin D induces fetal hemoglobin synthesis in K562 cells and human hematopoietic progenitors through activation of p38 pathway and stabilization of the γ-globin mRNA. |
| PubMed:Studies toward the total syntheses of cucurbitacins B and D. |
| PubMed:New cucurbitane-type triterpenoids from Bryonia aspera. |
| PubMed:Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands. |
| PubMed:Cucurbitacin D isolated from Trichosanthes kirilowii induces apoptosis in human hepatocellular carcinoma cells in vitro. |
| PubMed:Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity. |
| PubMed:Phytochemical and biological investigation of Begonia heracleifolia. |
| PubMed:Cucurbitane triterpenes from the fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus. |
| PubMed:Effect of cucurbitacins on bilirubin-albumin binding in human plasma. |
| PubMed:Pregnane, coumarin and lupane derivatives and cytotoxic constituents from Helicteres angustifolia. |
| PubMed:[Relationships of Aulacophora beetles feeding behavior with cucurbitacin types in host crops]. |
| PubMed:A new cucurbitacin D related 16,23-epoxy derivative and its isomerization products. |
| PubMed:Inhibition of nitric oxide generation by 23,24-dihydrocucurbitacin D in mouse peritoneal macrophages. |
| PubMed:Cytotoxic cucurbitacin constituents from Sloanea zuliaensis. |
| PubMed:Cucurbitacins from Trichosanthes kirilowii as the inhibitory components on tyrosinase activity and melanin synthesis of B16/F10 melanoma cells. |
| PubMed:Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii. |
| PubMed:Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor. |
| PubMed:Cytotoxic constituents ofSorbaria sorbifolia var.stellipila. |
| PubMed:Effect of cucurbitacin D on in vitro growth of Xenorhabdus and Photorhabdus spp., symbiotic bacteria of entomopathogenic nematodes. |
| PubMed:[Studies on the constituents of "Trichosanthes root". IV. Constituents of roots of Trichosanthes multiloba Miq., Trichosanthes miyagii Hay. and Chinese crude drug "karo-kon"]. |
| PubMed:[Studies on the constituents of trichosanthes root. III. Constituents of roots of Trichosanthes bracteata Voigt]. |
| PubMed:[Studies on the constituents of trichosanthes root. I. Constituents of roots of Trichosanthes kirilowii Maxim. var. japonicum Kitam]. |
| PubMed:Cucurbitacins : Plant-derived defense compounds for diabroticites (Coleoptera: Chrysomelidae). |
| PubMed:[Poisoning with a kind of Bitter Edible Gourd]. |
| PubMed:Pharmaco-dynamic activity of elatericin (cucurbitacin D). |
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