cucurbitacin D
19-nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-
 
Notes:
Isol. from plants of the Cucurbitaceae
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      Product(s):
      3877-86-9 Cucurbitacin D >98%
      Source from rhizomes of Hemsleya amabilis Diels. It might be a new therapeutic option for the treatment of endometrial and ovarian cancers,
       
       
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CAS Number: 3877-86-9Picture of molecule3D/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 or firefox)
Category: pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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US Patents: Search
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PubMed: Search
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Cucurbitacin D 98%
BOC Sciences
For experimental / research use only.
Cucurbitacin D >98%
Odor: characteristic
Use: Source from rhizomes of Hemsleya amabilis Diels. It might be a new therapeutic option for the treatment of endometrial and ovarian cancers,
ExtraSynthese
For experimental / research use only.
Cucurbitacin D (HPLC) ≥95%
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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
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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.
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Safety References:
EPI System: View
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
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C08796
HMDB (The Human Metabolome Database): HMDB34695
FooDB: FDB013225
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cucumber sprout
Search Trop  Picture
 gourd calabash gourd fruit
Search Trop  Picture
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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-norlanosta-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-
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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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