| Common Name |
5-Hydroxylysine
| Description |
5-Hydroxylysine is a hydroxylated derivative of the amino acid lysine that is present in certain collagens. Hydroxylysine is an amino acid and is most widely known as a component of collagen. A standard amino acid with the R group consisting of an amino terminated butyl hydrocarbon chain, with a hydroxyl group on the carbon atom before the amino group.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(2S,5R)-5-HydroxylysineChEBI
(5R)-5-Hydroxy-L-lysineChEBI
alpha,epsilon-diamino-delta-Hydroxycaproic acidChEBI
L-erythro-5-HydroxylysineChEBI
L-Normal-5-hydroxylysineChEBI
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
a,epsilon-diamino-δ-hydroxycaproateGenerator
a,epsilon-diamino-δ-hydroxycaproic acidGenerator
(2S,5R)-2,6-diamino-5-HydroxyhexanoateHMDB
(2S,5R)-2,6-diamino-5-Hydroxyhexanoic acidHMDB
5-Hydroxy-L-lysineHMDB
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
HydroxylysineHMDB
L-D-HydroxylysineHMDB
L-delta-HydroxylysineHMDB
Procollagen 5-hydroxy-L-lysineHMDB
Procollagen L-erythro-5-hydroxy-L-lysineHMDB
2,6-diamino-5-Hydroxyhexanoic acidMeSH
| Chemical Formlia |
C6H14N2O3
| Average Molecliar Weight |
162.187
| Monoisotopic Molecliar Weight |
162.100442324
| IUPAC Name |
(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid
| Traditional Name |
L-hydroxylysine
| CAS Registry Number |
1190-94-9
| 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 Key |
YSMODUONRAFBET-UHNVWZDZSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
L-alpha-amino acids
| Alternative Parents |
Medium-chain fatty acids
Hydroxy fatty acids
Amino fatty acids
Secondary alcohols
Amino acids
1,2-aminoalcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
hydroxy-L-lysine (CHEBI:18040 )
5-hydroxylysine (CHEBI:18040 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility23 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility124.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.17 m3·mol-1ChemAxon
Polarizability16.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-004i-1900000000-af0587f21cf098832243View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-e76f81591af86b08b817View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-cc12ca7d17e7da426b8eView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Cerebrospinal Fluid (CSF)
Feces
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0-2.5 uMNewborn (0-30 days old)Both
Normal
BC Children's Hos…
details
BloodDetected and Quantified0-2.5 uMInfant (1 – 3 months old)Both
Normal
BC Children's Hos…
details
BloodDetected and Quantified0-2.5 uMChildren (3 months – 6 years old)Both
Normal
BC Children's Hos…
details
BloodDetected and Quantified0-2.5 uMChildren (6 – 18 years old)Both
Normal
BC Children's Hos…
details
BloodDetected and Quantified2.5 (1.8-3.2) uMAdlit (>18 years old)BothNormal
Geigy Scientific …
details
Cerebrospinal Fluid (CSF)Detected and Quantified0-0.8 uMChildren (0 – 10 years old)Both
Normal
BC Children's Hos…
details
Cerebrospinal Fluid (CSF)Detected and Quantified0-0.8 uMAdolescent (>11 years old)Both
Normal
BC Children's Hos…
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
25486321
details
FecesDetected but not Quantified Adlit (>18 years old)FemaleNormal
26709303
details
UrineDetected and Quantified4.97 – 116.90 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified2.04 – 71.91 umol/mmol creatinineInfant (1 – 6 months old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified2.04 – 71.91 umol/mmol creatinineInfant (6 months – <1 year old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified2.04 – 71.91 umol/mmol creatinineChildren (1 – 2 years old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified0 – 8.03 umol/mmol creatinineChildren (2 – 4 years old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified0 – 8.03 umol/mmol creatinineChildren (4 – 13 years old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified0 – 8.03 umol/mmol creatinineAdolescent (13 – 21 years old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified0 – 8.03 umol/mmol creatinineAdlit (>21 years old)Both
Normal
BC Children's Hos…
details
UrineDetected and Quantified0.11 umol/mmol creatinineAdlit (>18 years old)BothNormal
19309105
details
UrineDetected and Quantified0.78-1.2 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified1.0 (0.45-2.26) umol/mmol creatinineAdlit (>18 years old)BothNormal
5472370
details
UrineDetected and Quantified0.82-1.2 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
UrineDetected and Quantified0.35 +/- 0.62 umol/mmol creatinineInfant (0-1 year old)BothNormal
2026685
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.50 +/- 0.028 uMElderly (>65 years old)BothAlzheimers disease
17031479
details
UrineDetected and Quantified7.262 +/- 2.023 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Eosinophilic esophagitis
Mordechai, Hien, …
details
| Associated Disorders and Diseases |
| Disease References |
| Alzheimers disease |
- Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimers disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
| Associated OMIM IDs |
104300 (Alzheimer's disease)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB012682
| KNApSAcK ID |
Not Available
| Chemspider ID |
2297721
| KEGG Compound ID |
C16741
| BioCyc ID |
CPD-7689
| BiGG ID |
53055
| Wikipedia Link |
Hydroxylysine
| NuGOwiki Link |
HMDB00450
| Metagene Link |
HMDB00450
| METLIN ID |
5439
| PubChem Compound |
3032849
| PDB ID |
LYZ
| ChEBI ID |
18040
Product: CA-074 methyl ester
References |
| Synthesis Reference |
Allevi, P.; Anastasia, M. Synthesis of all four possible stereoisomers of 5-hydroxylysine. Tetrahedron: Asymmetry (2000), 11(15), 3151-3160. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- 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 ]
- 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 ]
- 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 ]
|
Enzymes
- 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
- 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
- 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
- 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-lysine |
details |
PMID: 11169622