MiMeDB: Showing metabocard for L-4-hydroxyglutamic semialdehyde (MMDBc0033098)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:42 UTC

Update Date

2024-04-30 20:00:10 UTC

Metabolite ID

MMDBc0033098

Metabolite Identification

Common Name

L-4-hydroxyglutamic semialdehyde

Description

L-4-Hydroxyglutamate semialdehyde is an intermediate in arginine and proline metabolism. L-4-Hydroxyglutamate semialdehyde is the 4th to last step in the synthesis of glyoxylate and is converted from L-erythro-4-hydroxyglutamate via the enzyme 1-pyrroline-5-carboxylate dehydrogenase [EC 1.5.1.12]. It is then converted to L-1-pyrroline-3-hydroxy-5-carboxylate via enzymatic reaction.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(4R)-4-Hydroxy-5-oxo-L-norvaline	ChEBI
4-Amino-3,4-dideoxy-D-erythro-penturonic acid	ChEBI
4-Amino-3,4-dideoxy-D-erythro-penturonate	Generator
L-4-Hydroxyglutamic acid semialdehyde	Generator

Molecular Formula

C₅H₉NO₄

Average Mass

147.1293

Monoisotopic Mass

147.053157781

IUPAC Name

(2S,4R)-2-amino-4-hydroxy-5-oxopentanoic acid

Traditional Name

(2S,4R)-2-amino-4-hydroxy-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](C[C@@H](O)C=O)C(O)=O

InChI Identifier

InChI=1S/C5H9NO4/c6-4(5(9)10)1-3(8)2-7/h2-4,8H,1,6H2,(H,9,10)/t3-,4+/m1/s1

InChI Key

XCXUZPXOFFRGGP-DMTCNVIQSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Short-chain hydroxy acid
Fatty acid
1,3-aminoalcohol
Alpha-hydroxyaldehyde
Secondary alcohol
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutamic semialdehyde (CHEBI:27809 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	128 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.3	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	8.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.81 m³·mol⁻¹	ChemAxon
Polarizability	13.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9200000000-e3513bbcdad456a12235	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ec-9650000000-7cae4c2fbcbbcab5eb31	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-2900000000-c81023046fb0eb6b2f5c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ul9-9400000000-810b28d67c6140132eb6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-35f89694ea3df06bc823	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-3900000000-23e55cd80e109069331a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9400000000-b630a7dba403bb557591	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-e8a60496d8e8def4b4ec	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-3900000000-a27391009bcba0d96f5e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-9400000000-08aa4f495f99db7ac2c1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a9698c2851b8d21d014c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fl0-9600000000-066024b26e64bc43b24f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-be9a96b507fb4c6e4e62	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001u-9000000000-a50a3005088f974da1e6	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191827	Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial	Unknown	P30038	Homo sapiens
MMDBp0193396	Proline dehydrogenase 1, mitochondrial	Unknown	O43272	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000094	L-4-hydroxyglutamic semialdehyde	L-Glutamyl-tRNA(Glu)	aldehyde dehydrogenase 4 family, member A1		VMH; KEGG	15849464
MMDBr0001929	Pyrroline hydroxycarboxylic acid	L-4-hydroxyglutamic semialdehyde	Not Available		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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

External Links

HMDB ID

HMDB0006556

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023970

KNApSAcK ID

Not Available

Chemspider ID

389693

KEGG Compound ID

C05938

BioCyc ID

Not Available

BiGG ID

1447438

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440851

PDB ID

Not Available

ChEBI ID

27809

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Knight J, Holmes RP: Mitochondrial hydroxyproline metabolism: implications for primary hyperoxaluria. Am J Nephrol. 2005 Mar-Apr;25(2):171-5. doi: 10.1159/000085409. Epub 2005 Apr 21. [PubMed:15849464 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for L-4-hydroxyglutamic semialdehyde (MMDBc0033098)

MOL for #<Metabolite:0x00007fdb5893a540>

3D MOL for #<Metabolite:0x00007fdb5893a540>

3D SDF for #<Metabolite:0x00007fdb5893a540>

3D-SDF for #<Metabolite:0x00007fdb5893a540>

PDB for #<Metabolite:0x00007fdb5893a540>

3D PDB for #<Metabolite:0x00007fdb5893a540>

SMILES for #<Metabolite:0x00007fdb5893a540>

INCHI for #<Metabolite:0x00007fdb5893a540>

Structure for #<Metabolite:0x00007fdb5893a540>

3D Structure for #<Metabolite:0x00007fdb5893a540>