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Showing NP-Card for 5-Hydroxylysine (NP0001396)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:02 UTC
NP-MRD IDNP0001396
Secondary Accession NumbersNone
Natural Product 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 NP0001396 (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
Download

3D MOL for NP0001396 (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
Download

3D SDF for NP0001396 (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>
NP0001396

> <DATABASE_NAME>
NP-MRD

> <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 NP0001396 (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
Download

PDB for NP0001396 (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
Download

3D PDB for NP0001396 (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
Download

SMILES for NP0001396 (5-Hydroxylysine)

NC[C@H](O)CC[C@H](N)C(O)=O
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INCHI for NP0001396 (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 JSmol
Synonyms
ValueSource
(2S,5R)-5-HydroxylysineChEBI
(5R)-5-Hydroxy-L-lysineChEBI
alpha,epsilon-Diamino-delta-hydroxycaproic acidChEBI
L-Erythro-5-hydroxylysineChEBI
L-Normal-5-hydroxylysineChEBI
5-Hydroxy-L-lysineKegg
a,epsilon-Diamino-delta-hydroxycaproateGenerator
a,epsilon-Diamino-delta-hydroxycaproic acidGenerator
alpha,epsilon-Diamino-delta-hydroxycaproateGenerator
Α,epsilon-diamino-δ-hydroxycaproateGenerator
Α,epsilon-diamino-δ-hydroxycaproic acidGenerator
Lysine, 5 hydroxyHMDB
2,6-Diamino-5-hydroxyhexanoic acidHMDB
5 HydroxylysineHMDB
HydroxylysineHMDB
(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acidHMDB
2,6 Diamino 5 hydroxyhexanoic acidHMDB
a,epsilon-Diamino-δ-hydroxycaproateHMDB
a,epsilon-Diamino-δ-hydroxycaproic acidHMDB
(2S,5R)-2,6-Diamino-5-hydroxyhexanoateHMDB
5-Hydroxy-lysineHMDB
D-Hydroxy-L-lysineHMDB
D-HydroxylysineHMDB
delta-DL-HydroxylysineHMDB
delta-Hydroxy-L-lysineHMDB
delta-HydroxylysineHMDB
Erythro-5-hydroxy-L-lysineHMDB
Hydroxy-lysineHMDB
L-D-HydroxylysineHMDB
L-delta-HydroxylysineHMDB
Procollagen 5-hydroxy-L-lysineHMDB
Procollagen L-erythro-5-hydroxy-L-lysineHMDB
5-HYDROXYLYSINEChEBI
Chemical FormulaC6H14N2O3
Average Mass162.1870 Da
Monoisotopic Mass162.10044 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Medicago sativaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Scolopendra subspinipesLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vicia fabaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility23 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP-3.8ALOGPS
logP-4.4ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.17 m³·mol⁻¹ChemAxon
Polarizability16.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000450
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  5. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  6. 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 ]