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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Hydroxy-L-proline (HMDB02113)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:37 -0600
Update Date 2013-02-08 17:11:24 -0700
HMDB ID HMDB02113
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Hydroxy-L-proline
Description Constituent of collagen and the antibiotic Telomycin (Combined Chemical Dictionary).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Procollagen trans-3-hydroxy-L-proline
Chemical Formula C5H9NO3
Average Molecular Weight 131.1299
Monoisotopic Molecular Weight 131.058243159
IUPAC Name (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid
Traditional IUPAC Name (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid
CAS Registry Number 4298-08-2
SMILES O[C@H]1CCN[C@H]1C(O)=O
InChI Identifier InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1
InChI Key BJBUEDPLEOHJGE-IUYQGCFVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • 1,2 Aminoalcohol
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Pyrrolidine
  • Pyrrolidine Carboxylic Acid
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 235 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 431 g/L ALOGPS
LogP -3.18 ALOGPS
LogP -3.7 ChemAxon
LogS 0.52 ALOGPS
pKa (strongest acidic) 1.61 ChemAxon
pKa (strongest basic) 10.62 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 69.56 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 29.38 ChemAxon
Polarizability 12.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011875
KNApSAcK ID Not Available
Chemspider ID 9312313 Link_out
KEGG Compound ID C04397 Link_out
BioCyc ID 3-HYDROXY-L-PROLINE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02113 Link_out
Metagene Link HMDB02113 Link_out
METLIN ID 6494 Link_out
PubChem Compound 11137200 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Sinha, Surajit; Tilve, Santosh; Chandrasekaran, Srinivasan. A convenient synthesis of trans-3-hydroxy-L-proline. ARKIVOC (Gainesville, FL, United States) (2005), (11), 209-217.
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available
Enzymes
Name: Prolyl 3-hydroxylase 1
Reactions:
  • procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
Gene Name: LEPRE1
Uniprot ID: Q32P28 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prolyl 3-hydroxylase 2
Reactions:
  • procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
Gene Name: LEPREL1
Uniprot ID: Q8IVL5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prolyl 3-hydroxylase 3
Reactions:
  • procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
Gene Name: LEPREL2
Uniprot ID: Q8IVL6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA