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618-27-9 molecular structure
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(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid

ChemBase ID: 69681
Molecular Formular: C5H9NO3
Molecular Mass: 131.12986
Monoisotopic Mass: 131.05824315
SMILES and InChIs

SMILES:
C(=O)([C@@H]1NC[C@@H](C1)O)O
Canonical SMILES:
O[C@H]1CN[C@H](C1)C(=O)O
InChI:
InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m1/s1
InChIKey:
PMMYEEVYMWASQN-QWWZWVQMSA-N

Cite this record

CBID:69681 http://www.chembase.cn/molecule-69681.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid
IUPAC Traditional name
cis-4-hydroxy-D-proline
Synonyms
(2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid
D-allo-Hydroxyproline
cis-4-Hydroxy-D-proline
cis-(-)-4-Hydroxy-L-proline
(2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid
cis-4-Hydroxy-D-proline
(2R,4R)-(+)-4-Hydroxypyrrolidine-2-carboxylic acid
H-D-cis-Hyp-OH
顺-4-羟基-D-脯氨酸
CAS Number
618-27-9
2584-71-6
EC Number
219-963-5
MDL Number
MFCD00005252
Beilstein Number
81439
PubChem SID
24895713
162035407
PubChem CID
440014

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.641382  H Acceptors
H Donor LogD (pH = 5.5) -3.7163465 
LogD (pH = 7.4) -3.7165344  Log P -3.7163188 
Molar Refractivity 29.3822 cm3 Polarizability 11.9828205 Å3
Polar Surface Area 69.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
243 °C (dec.)(lit.) expand Show data source
243°C dec. expand Show data source
257°C expand Show data source
Optical Rotation
[α]20/D +60±1°, c = 1% in H2O expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥99.0% (NT) expand Show data source
95+% expand Show data source
98+% expand Show data source
Empirical Formula (Hill Notation)
C5H9NO3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - H5877 external link
Packaging
1, 10 g in poly bottle
250 mg in poly bottle
Biochem/physiol Actions
Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H5877.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - 56246 external link
Biochem/physiol Actions
Cis-4-hydroxy-D-proline is a pharmaceutically active, anti-convulsive, amino acid transported by the proton coupled amino acid transporter (PAT1) expressed in intestine and brain. Cis-4-hydroxy-D-proline upregulates the expression of the hydroxyproline transporter hypM in legume endosymbiont Sinorhizobium meliloti.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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