Basic information
- CAS
6199-67-3- Standard SMILES
CC(=O)OC(C)(C)/C=C/C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C- InChIKey
IXQKXEUSCPEQRD-OUKQBFOZSA-N- Molecular formula
- C32H46O8
- Average molar mass
- 558.7 g/mol
- Monoisotopic mass
- 558.31926842
Names & identifiers
- Preferred name
- [(E)-5-(2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate
- IUPAC
- [(E)-6-(2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
- English name
- CUCURBITACIN B
- Molecular formula
- C32H46O8
- Molecular weight
- 558.7
Names & synonyms
MLS002702988Amarin?Cucurbitacin B [M+H]+CHEMBL1728549EBC-615351AS-75927SMR001566797(2E)-5-(2,16-Dihydroxy-4,4,9,14-tetramethyl-3,11-dioxoestr-5-en-17-yl)-5-hydroxy-1,1-dimethyl-4-oxohex-2-en-1-yl acetate[(E)-5-(2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate6-{2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetateCucurbitacinCuc B
Show more names
AMARINEHSDB 3476DATISCACINNSC-144154heMsecin Acucuritacin BcucurbitacinebCUCURBITACIN B
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 1,210
Experimental & physicochemical properties
Melting Point180 - 182 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 184 · 184-186°
- alpha
- 25 · D25 +88° (c = 1.55 in ethanol)
- Boiling point
- 546.74 °C · 546.74°C (rough estimate)
- Density
- 1.0953 · 1.0953 (rough estimate)
- refractive index
- 1.49 · 1.4900 (estimate)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- 10 mg/mL, · DMSO: soluble10mg/mL, clear
- form
- powder
- pka
- 12.6 · 12.60±0.29(Predicted)
- color
- white to beige
- λmax
- 290 nm · 290nm(EtOH)(lit.)
- Merck
- 14 · 14,2614
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- RC6190000
- ridadr
- UN 2811 6.1 / PGI
- hs_code
- 29153900
- Toxicity
- LD10 orally in mice: 5 mg/kg (LeMen)
- risk_code
- 25
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 45-24/25
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H300
- Hazard Classifications
- Acute Tox. 2 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
- Hazardous Substances Data
- 6199-67-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionCucurbitacin B is a tetracyclic triterpenoid that has been shown to have a strong antitumor activity.
UsesCucurbitacin B hydrate has been used: as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs).as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies.to determine its effect on the cell viability of pancreatic cancer cell lines.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
上海波以尔化工有限公司
Related reactions
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Compound notes
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