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Showing metabocard for 5-Hydroxylysine (HMDB0000450)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:01 UTC
HMDB IDHMDB0000450
Secondary Accession Numbers
  • HMDB0006827
  • HMDB00450
  • HMDB06827
Metabolite Identification
Common Name5-Hydroxylysine
Description5-Hydroxylysine (Hyl), also known as hydroxylysine or 5-Hydroxy-L-lysine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. 5-Hydroxylysine is a hydroxylated derivative of the amino acid lysine that is present in certain collagens, the chief structural protein of mammalian skin and connective tissue. 5-Hydroxylysine arises from a post-translational hydroxy modification of lysine and is biosynthesized from lysine via oxidation by lysyl hydroxylase enzymes. 5-Hydroxylysine can then undergo further modification by glycosylation, giving rise to galactosyl hydroxylysine (GH) and glucosylgalactosyl hydroxylysine (GGH). These glycosylated forms of hydroxylysine contribute to collagen’s unusual toughness and resiliency. The monoglycosylated, galactosyl-hydroxylysine is enriched in bone compared with the disaccharide form, glucosyl-galactosyl-hydroxylysine, which is the major form in skin. 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. It was first discovered in 1921 by Donald Van Slyke. Free forms of hydroxylysine arise through proteolytic degradation of collagen. Urinary excretion of 5-Hydroxylysine and its glycosides can be used as an index of collagen degradation, with high levels being indicative of more rapid or extensive collagen degradation (often seen in patients with thermal burns, Paget's disease of bone or hyperphosphatasia) (PMID: 404321 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000450 (5-Hydroxylysine)

  Mrv1652310281915522D          

 11 10  0  0  0  0            999 V2000
 9991.8108 9991.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0969 9991.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9991.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.6675 9991.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9529 9991.6646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9991.2527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2417 9991.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9551 9991.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2417 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9990.4280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  6  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0000450 (5-Hydroxylysine)

HMDB0000450
     RDKit          3D
5-Hydroxylysine
 25 24  0  0  0  0  0  0  0  0999 V2000
    2.9740    1.3928    0.0716 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7957    0.3096   -0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695   -0.5653   -0.3198 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3996   -1.6442   -1.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.3100   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -0.5616    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717    0.1916    0.5418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9453   -0.7692    1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.7666   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    1.6610   -1.3030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174    0.3626   -1.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7944    2.3166   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216    1.3167    0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.7073   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -0.3010   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059   -0.9387    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -2.3213   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    1.1626    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.6224   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -1.4084   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.0629    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587    0.9618    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0230   -0.7333    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -1.6954    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4401   -0.0803   -0.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  1
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
 11 25  1  0
M  END
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3D SDF for HMDB0000450 (5-Hydroxylysine)

  Mrv1652310281915522D          

 11 10  0  0  0  0            999 V2000
 9991.8108 9991.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0969 9991.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9991.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.6675 9991.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9529 9991.6646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9991.2527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2417 9991.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9551 9991.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2417 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9990.4280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  6  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000450

> <DATABASE_NAME>
hmdb

> <SMILES>
NC[C@H](O)CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1

> <INCHI_KEY>
YSMODUONRAFBET-UHNVWZDZSA-N

> <FORMULA>
C6H14N2O3

> <MOLECULAR_WEIGHT>
162.187

> <EXACT_MASS>
162.100442324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.54664931761117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid

> <ALOGPS_LOGP>
-3.77

> <JCHEM_LOGP>
-4.414212989148228

> <ALOGPS_LOGS>
-0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.903490442523363

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4473857532646233

> <JCHEM_PKA_STRONGEST_BASIC>
9.746257700424144

> <JCHEM_POLAR_SURFACE_AREA>
109.57

> <JCHEM_REFRACTIVITY>
39.17100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-hydroxylysine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000450 (5-Hydroxylysine)

HMDB0000450
     RDKit          3D
5-Hydroxylysine
 25 24  0  0  0  0  0  0  0  0999 V2000
    2.9740    1.3928    0.0716 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7957    0.3096   -0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695   -0.5653   -0.3198 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3996   -1.6442   -1.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.3100   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -0.5616    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717    0.1916    0.5418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9453   -0.7692    1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.7666   -0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    1.6610   -1.3030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174    0.3626   -1.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7944    2.3166   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216    1.3167    0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.7073   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -0.3010   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059   -0.9387    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -2.3213   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    1.1626    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.6224   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -1.4084   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.0629    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587    0.9618    1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0230   -0.7333    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128   -1.6954    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4401   -0.0803   -0.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  1
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
 11 25  1  0
M  END
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PDB for HMDB0000450 (5-Hydroxylysine)

HEADER    PROTEIN                                 28-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-OCT-19         0                                  
HETATM    1  C   UNK     0    8651.3808651.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8650.0488650.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8648.7148651.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8647.3798650.338   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8646.0458651.107   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0    8648.7148652.648   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8652.7168650.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8654.0518651.107   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8655.3838650.338   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8654.0518652.648   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8652.7168648.799   0.000  0.00  0.00           N+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0000450 (5-Hydroxylysine)

COMPND    HMDB0000450
HETATM    1  N1  UNL     1       2.974   1.393   0.072  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.796   0.310  -0.864  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.669  -0.565  -0.320  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.400  -1.644  -1.130  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.427   0.310  -0.187  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.683  -0.562   0.352  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.972   0.192   0.542  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.945  -0.769   1.066  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.503   0.767  -0.696  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.868   1.661  -1.303  1.00  0.00           O  
HETATM   11  O3  UNL     1      -3.717   0.363  -1.258  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.794   2.317  -0.334  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.822   1.317   0.646  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.501   0.707  -1.852  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.696  -0.301  -1.018  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.906  -0.939   0.684  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.124  -2.321  -1.019  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.649   1.163   0.453  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.184   0.622  -1.239  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.865  -1.408  -0.368  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.353  -1.063   1.288  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.859   0.962   1.325  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.023  -0.733   2.094  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.713  -1.695   0.672  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.440  -0.080  -0.718  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3   14   15
CONECT    3    4    5   16
CONECT    4   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24
CONECT    9   10   10   11
CONECT   11   25
END
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SMILES for HMDB0000450 (5-Hydroxylysine)

NC[C@H](O)CC[C@H](N)C(O)=O
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INCHI for HMDB0000450 (5-Hydroxylysine)

InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H14N2O3
Average Molecular Weight162.187
Monoisotopic Molecular Weight162.100442324
IUPAC Name(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid
Traditional NameL-hydroxylysine
CAS Registry Number1190-94-9
SMILES
NC[C@H](O)CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1
InChI KeyYSMODUONRAFBET-UHNVWZDZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • 1,2-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility23 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available133.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000015
[M+H]+Not Available135.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000015
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.50 +/- 0.028 uMElderly (>65 years old)BothAlzheimer's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified20.963 umol/mmol creatinineAdolescent (13-18 years old)MaleHydroxylysinuria details
UrineDetected and Quantified7.262 +/- 2.023 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified5.507-7.110 umol/mmol creatinineAdolescent (13-18 years old)MaleHydroxylysinuria details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Hydroxylysinuria
  1. Hoefnagel D, Pomeroy J: Hydroxylysinuria. Lancet. 1970 Jun 20;760(1):1342-3. [PubMed:4194840 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012682
KNApSAcK IDNot Available
Chemspider ID2297721
KEGG Compound IDC16741
BioCyc IDCPD-14226
BiGG ID53055
Wikipedia LinkHydroxylysine
METLIN ID5439
PubChem Compound3032849
PDB IDNot Available
ChEBI ID18040
Food Biomarker OntologyNot Available
VMH IDPCOLLG5HLYS
MarkerDB IDMDB00000163
Good Scents IDNot Available
References
Synthesis ReferenceAllevi, P.; Anastasia, M. Synthesis of all four possible stereoisomers of 5-hydroxylysine. Tetrahedron: Asymmetry (2000), 11(15), 3151-3160.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
  2. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  3. Schor DS, Verhoeven NM, Struys EA, ten Brink HJ, Jakobs C: Quantification of 3-hydroxyglutaric acid in urine, plasma, cerebrospinal fluid and amniotic fluid by stable-isotope dilution negative chemical ionization gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):199-204. [PubMed:12383496 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  5. Krane SM, Kantrowitz FG, Byrne M, Pinnell SR, Singer FR: Urinary excretion of hydroxylysine and its glycosides as an index of collagen degradation. J Clin Invest. 1977 May;59(5):819-27. doi: 10.1172/JCI108704. [PubMed:404321 ]

Enzymes

Enzyme Details
1. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD1
Uniprot ID:
Q02809
Molecular weight:
83549.55
Enzyme Details
2. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 2
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD2
Uniprot ID:
O00469
Molecular weight:
84685.07
Enzyme Details
3. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 3
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD3
Uniprot ID:
O60568
Molecular weight:
84784.505
Enzyme Details
4. Hydroxylysine kinase
General function:
Not Available
Specific function:
Catalyzes the GTP-dependent phosphorylation of 5-hydroxy-L-lysine.
Gene Name:
AGPHD1
Uniprot ID:
A2RU49
Molecular weight:
41932.82
Reactions
Guanosine triphosphate + 5-Hydroxylysine → Guanosine diphosphate + 5-phosphonooxy-L-lysinedetails