Cucurbitacin D

Names

[ Name ]:
Cucurbitacin D

[Synonym ]:
(2S,4R,9β,16α,23E)-2,16,20,25-Tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-5,23-diene-1,11,22-trione
(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
Elatericine A
Estr-5-ene-3,11-dione, 17-[(1R,3E)-1,5-dihydroxy-1,5-dimethyl-2-oxo-3-hexen-1-yl]-2,16-dihydroxy-4,4,9,14-tetramethyl-, (2β,9β,10α,16α,17β)-
Elatericin A
Estr-5-ene-3,11-dione, 17-[(1R,3E)-1,5-dihydroxy-1,5-dimethyl-2-oxo-3-hexen-1-yl]-2,16-dihydroxy-4,4,9,14-tetramethyl-, (2β,8ξ,9β,10α,16α,17β)-
(2S,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-1H-cyclopenta[a]phenanthrene-3,11(2H,4H)-dione
Cucurbitacin D
(2S,4R,8ξ,9β,16α,23E)-2,16,20,25-Tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-5,23-diene-1,11,22-trione
(2S,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-1H-cyclopenta[a]phenanthren-3,11(2H,4H)-dion

Biological Activity

[Description]:

Cucurbitacin D is an active component in Cucurbita texana, disrupts interactions between Hsp90 and two co-chaperones, Cdc37 and p23. Cucurbitacin D prevents Hsp90 client (Her2, Raf, Cdk6, pAkt) maturation without induction of the heat shock response. Anti-cancer activity[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> HSP

Signaling Pathways >> Cell Cycle/DNA Damage >> HSP

[Target]

HSP90

[References]

[1]. Hall JA, et al. Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery. J Nat Prod. 2015 Apr 24;78(4):873-9.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
684.0±55.0 °C at 760 mmHg

[ Melting Point ]:
151-152ºC

[ Molecular Formula ]:
C₃₀H₄₄O₇

[ Molecular Weight ]:
516.666

[ Flash Point ]:
381.4±28.0 °C

[ Exact Mass ]:
516.308716

[ PSA ]:
132.13000

[ LogP ]:
1.48

[ Vapour Pressure ]:
0.0±4.8 mmHg at 25°C

[ Index of Refraction ]:
1.582

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC6170000

CHEMICAL NAME :: 19-Nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-tri one, 9-methyl-2-beta,16-alpha,20,25- tetrahydroxy-

CAS REGISTRY NUMBER :: 3877-86-9

LAST UPDATED :: 199712

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C30-H44-O7

MOLECULAR WEIGHT :: 516.74

WISWESSER LINE NOTATION :: L E5 B666 CV OV LUTJ B1 E1 FXQ1&V1U1XQ1&1 GQ I1 N1 N1 PQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8200 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1300 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3400 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes Nutritional and Gross Metabolic - body temperature increase

REFERENCE :: CHTPBA Chimica Therapeutica. (Paris, France) V.1-8, 1965-73. For publisher information, see EJMCA5. Volume(issue)/page/year: 4,459,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1750 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4600 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 960 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1000 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - nausea or vomiting

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 900 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - nausea or vomiting

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 130,315,1961

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ HS Code ]:
29144000