| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2021-08-09 22:33:02 UTC |
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| NP-MRD ID | NP0001396 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 5-Hydroxylysine |
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| Description | 5-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 ). |
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| Structure | NC[C@H](O)CC[C@H](N)C(O)=O 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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| Synonyms | | Value | Source |
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| (2S,5R)-5-Hydroxylysine | ChEBI | | (5R)-5-Hydroxy-L-lysine | ChEBI | | alpha,epsilon-Diamino-delta-hydroxycaproic acid | ChEBI | | L-Erythro-5-hydroxylysine | ChEBI | | L-Normal-5-hydroxylysine | ChEBI | | 5-Hydroxy-L-lysine | Kegg | | a,epsilon-Diamino-delta-hydroxycaproate | Generator | | a,epsilon-Diamino-delta-hydroxycaproic acid | Generator | | alpha,epsilon-Diamino-delta-hydroxycaproate | Generator | | Α,epsilon-diamino-δ-hydroxycaproate | Generator | | Α,epsilon-diamino-δ-hydroxycaproic acid | Generator | | Lysine, 5 hydroxy | HMDB | | 2,6-Diamino-5-hydroxyhexanoic acid | HMDB | | 5 Hydroxylysine | HMDB | | Hydroxylysine | HMDB | | (2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid | HMDB | | 2,6 Diamino 5 hydroxyhexanoic acid | HMDB | | a,epsilon-Diamino-δ-hydroxycaproate | HMDB | | a,epsilon-Diamino-δ-hydroxycaproic acid | HMDB | | (2S,5R)-2,6-Diamino-5-hydroxyhexanoate | HMDB | | 5-Hydroxy-lysine | HMDB | | D-Hydroxy-L-lysine | HMDB | | D-Hydroxylysine | HMDB | | delta-DL-Hydroxylysine | HMDB | | delta-Hydroxy-L-lysine | HMDB | | delta-Hydroxylysine | HMDB | | Erythro-5-hydroxy-L-lysine | HMDB | | Hydroxy-lysine | HMDB | | L-D-Hydroxylysine | HMDB | | L-delta-Hydroxylysine | HMDB | | Procollagen 5-hydroxy-L-lysine | HMDB | | Procollagen L-erythro-5-hydroxy-L-lysine | HMDB | | 5-HYDROXYLYSINE | ChEBI |
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| Chemical Formula | C6H14N2O3 |
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| Average Mass | 162.1870 Da |
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| Monoisotopic Mass | 162.10044 Da |
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| IUPAC Name | (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid |
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| Traditional Name | L-hydroxylysine |
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| CAS Registry Number | 1190-94-9 |
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| SMILES | NC[C@H](O)CC[C@H](N)C(O)=O |
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| 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 |
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| InChI Key | YSMODUONRAFBET-UHNVWZDZSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | L-alpha-amino acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 23 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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