H1637
cis-4-Hydroxy-L-proline
collagen synthesis inhibitor
Synonym(s):
(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP
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About This Item
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81440
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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Quality Level
Assay
≥98% (TLC)
form
powder
technique(s)
ligand binding assay: suitable
color
white to faint yellow
mp
257 °C (dec.) (lit.)
application(s)
peptide synthesis
SMILES string
O[C@@H]1CN[C@@H](C1)C(O)=O
InChI
1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
InChI key
PMMYEEVYMWASQN-IMJSIDKUSA-N
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Application
cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.
Biochem/physiol Actions
cis-4-Hydroxy-L-proline (CHP) and its derivatives may have anticancer activity. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.
Other Notes
Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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