MiMeDB: Showing metabocard for 5-Hydroxylysine (MMDBc0000344)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:47 UTC

Update Date

2024-10-17 18:45:36 UTC

Metabolite ID

MMDBc0000344

Metabolite Identification

Common Name

5-Hydroxylysine

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‚Äôs 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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	MeSH
2,6-Diamino-5-hydroxyhexanoic acid	MeSH
5 Hydroxylysine	MeSH
Hydroxylysine	MeSH
(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid	MeSH
2,6 Diamino 5 hydroxyhexanoic acid	MeSH
a,epsilon-diamino-δ-hydroxycaproate	Generator, HMDB
a,epsilon-diamino-δ-hydroxycaproic acid	Generator, 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

Molecular Formula

C₆H₁₄N₂O₃

Average Mass

162.187

Monoisotopic Mass

162.100442324

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.50	0.028			uM	Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479
Human Urine	Detected and Quantified	20.963				umol/mmol creatinine	Adolescent (13-18 years old)	Male	Hydroxylysinuria	HMDB	4194840
Human Urine	Detected and Quantified			5.507	7.110	umol/mmol creatinine	Adolescent (13-18 years old)	Male	Hydroxylysinuria	HMDB	4194840
Human Urine	Detected and Quantified	0.11				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified	0.35	0.62			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified			0.78	1.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.82	1.2	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.0		0.45	2.26	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	5472370
Human Urine	Detected and Quantified	7.262	2.023			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0	8.03	umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	8.03	umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	8.03	umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			0	8.03	umol/mmol creatinine	Adult (>21 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.8	uM	Children (0 - 10 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.8	uM	Adolescent (>11 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			0	2.5	uM	Newborn (0-30 days old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			0	2.5	uM	Infant (1 - 3 months old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			0	2.5	uM	Children (3 months - 6 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified			0	2.5	uM	Children (6 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			2.04	71.91	umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			2.04	71.91	umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			2.04	71.91	umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified			4.97	116.90	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified	2.5		1.8	3.2	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	<1.36				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<16.97				umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<2.94				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<3.51				umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<3.85				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified	<6.45				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	26709303
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

References

Showing metabocard for 5-Hydroxylysine (MMDBc0000344)

MOL for #<Metabolite:0x00007fb809dcc2d8>

3D MOL for #<Metabolite:0x00007fb809dcc2d8>

3D SDF for #<Metabolite:0x00007fb809dcc2d8>

3D-SDF for #<Metabolite:0x00007fb809dcc2d8>

PDB for #<Metabolite:0x00007fb809dcc2d8>

3D PDB for #<Metabolite:0x00007fb809dcc2d8>

SMILES for #<Metabolite:0x00007fb809dcc2d8>

INCHI for #<Metabolite:0x00007fb809dcc2d8>

Structure for #<Metabolite:0x00007fb809dcc2d8>

3D Structure for #<Metabolite:0x00007fb809dcc2d8>