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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 15:44:17 UTC

Update Date

2023-02-21 17:17:20 UTC

HMDB ID

HMDB0006556

Secondary Accession Numbers

HMDB06556

Metabolite Identification

Common Name

L-4-Hydroxyglutamate semialdehyde

Description

L-4-Hydroxyglutamate semialdehyde, also known as (4R)-4-hydroxy-5-oxo-L-norvaline, 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. L-4-Hydroxyglutamate semialdehyde is a very strong basic compound (based on its pKa). A glutamic semialdehyde that is L-glutamic 5-semialdehyde substituted by a hydroxy group at position 4. L-4-Hydroxyglutamate semialdehyde exists in all living species, ranging from bacteria to humans. Within humans, L-4-hydroxyglutamate semialdehyde participates in a number of enzymatic reactions. In particular, L-4-hydroxyglutamate semialdehyde can be biosynthesized from 4-hydroxy-L-glutamic acid through the action of the enzyme proline dehydrogenase 1, mitochondrial. In addition, L-4-hydroxyglutamate semialdehyde can be biosynthesized from 4-hydroxy-L-glutamic acid through its interaction with the enzyme Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial. In humans, L-4-hydroxyglutamate semialdehyde is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006556)

Source

Endogenous

Endogenous (HMDB: HMDB0006556)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine and Proline Metabolism (HMDB: HMDB0006556)
Arginine and Proline Metabolism (HMDB: HMDB0006556)

Disease pathway

Prolidase Deficiency (PD) (PathBank: SMP0000207)
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency) (PathBank: SMP0000362)
Hyperprolinemia Type II (PathBank: SMP0000360)
Hyperprolinemia Type I (PathBank: SMP0000361)
Prolinemia Type II (PathBank: SMP0000208)
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) (PathBank: SMP0000188)
Ornithine Aminotransferase Deficiency (OAT Deficiency) (PathBank: SMP0000363)
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency (PathBank: SMP0000504)
Hyperornithinemia with Gyrate Atrophy (HOGA) (PathBank: SMP0000505)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0000506)
L-Arginine:Glycine Amidinotransferase Deficiency (PathBank: SMP0000507)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0120790)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.942	31661259
DarkChem	[M-H]-	132.226	31661259
DeepCCS	[M+H]+	131.621	30932474
DeepCCS	[M-H]-	128.813	30932474
DeepCCS	[M-2H]-	164.921	30932474
DeepCCS	[M+Na]+	140.336	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	126.9	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-4-Hydroxyglutamate semialdehyde	N[C@@H](C[C@@H](O)C=O)C(O)=O	2294.0	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde	N[C@@H](C[C@@H](O)C=O)C(O)=O	1193.5	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde	N[C@@H](C[C@@H](O)C=O)C(O)=O	1587.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-4-Hydroxyglutamate semialdehyde,1TMS,isomer #1	C[Si](C)(C)O[C@@H](C=O)C[C@H](N)C(=O)O	1515.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C=O	1422.1	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TMS,isomer #3	C[Si](C)(C)OC=C(O)C[C@H](N)C(=O)O	1591.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TMS,isomer #4	C[Si](C)(C)N[C@@H](C[C@@H](O)C=O)C(=O)O	1518.9	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)C[C@H](C=O)O[Si](C)(C)C	1539.1	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #2	C[Si](C)(C)OC=C(C[C@H](N)C(=O)O)O[Si](C)(C)C	1676.8	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #3	C[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C)C(=O)O	1613.5	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #4	C[Si](C)(C)OC=C(O)C[C@H](N)C(=O)O[Si](C)(C)C	1615.8	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #5	C[Si](C)(C)N[C@@H](C[C@@H](O)C=O)C(=O)O[Si](C)(C)C	1565.4	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C)C(=O)O	1702.3	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TMS,isomer #7	C[Si](C)(C)N([C@@H](C[C@@H](O)C=O)C(=O)O)[Si](C)(C)C	1701.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1697.9	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1655.5	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2090.9	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1648.5	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1647.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #2	C[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1803.1	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	1777.1	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	1706.1	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O	2063.4	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #4	C[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1776.3	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #4	C[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1677.9	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #4	C[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1971.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1730.5	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1693.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #5	C[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1997.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C)[Si](C)(C)C	1740.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C)[Si](C)(C)C	1655.1	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C)[Si](C)(C)C	2010.9	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #7	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1879.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #7	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1782.3	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TMS,isomer #7	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2132.4	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1778.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1743.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1831.0	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1818.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1768.7	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1728.7	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #3	C[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1905.3	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #3	C[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1836.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #3	C[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1970.7	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #4	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1886.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #4	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1834.7	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TMS,isomer #4	C[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1971.3	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TMS,isomer #1	C[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1946.9	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TMS,isomer #1	C[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1861.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TMS,isomer #1	C[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1819.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](C=O)C[C@H](N)C(=O)O	1755.4	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@@H](O)C=O	1667.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(O)C[C@H](N)C(=O)O	1820.1	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C=O)C(=O)O	1773.6	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C[C@H](C=O)O[Si](C)(C)C(C)(C)C	1979.3	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=C(C[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C	2121.8	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2068.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2066.1	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](C[C@@H](O)C=O)C(=O)O[Si](C)(C)C(C)(C)C	1987.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C(C)(C)C)C(=O)O	2161.6	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](C[C@@H](O)C=O)C(=O)O)[Si](C)(C)C(C)(C)C	2166.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2291.9	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2251.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2365.4	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2299.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2231.5	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2181.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O	2386.4	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O	2267.2	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O	2355.3	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2452.4	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2286.5	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](C=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2250.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2368.9	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2297.4	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CC(O)=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2327.1	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2394.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2277.4	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@@H](O)C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2269.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2503.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2376.7	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2398.2	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2569.7	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2445.9	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2310.0	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2690.6	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2511.4	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C[C@H](C=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2201.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2738.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2528.6	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2346.6	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2716.0	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2583.5	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2366.4	Standard polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2960.2	Semi standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2715.0	Standard non polar	33892256
L-4-Hydroxyglutamate semialdehyde,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2357.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-4-Hydroxyglutamate semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9200000000-e3513bbcdad456a12235	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-4-Hydroxyglutamate semialdehyde GC-MS (2 TMS) - 70eV, Positive	splash10-00ec-9650000000-7cae4c2fbcbbcab5eb31	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-4-Hydroxyglutamate semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 10V, Positive-QTOF	splash10-0f8a-2900000000-c81023046fb0eb6b2f5c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 20V, Positive-QTOF	splash10-0ul9-9400000000-810b28d67c6140132eb6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 40V, Positive-QTOF	splash10-0a4l-9000000000-35f89694ea3df06bc823	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 10V, Negative-QTOF	splash10-0002-3900000000-23e55cd80e109069331a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 20V, Negative-QTOF	splash10-00di-9400000000-b630a7dba403bb557591	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 40V, Negative-QTOF	splash10-05fr-9000000000-e8a60496d8e8def4b4ec	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 10V, Negative-QTOF	splash10-004j-3900000000-a27391009bcba0d96f5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 20V, Negative-QTOF	splash10-00dr-9400000000-08aa4f495f99db7ac2c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 40V, Negative-QTOF	splash10-0006-9000000000-a9698c2851b8d21d014c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 10V, Positive-QTOF	splash10-0fl0-9600000000-066024b26e64bc43b24f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 20V, Positive-QTOF	splash10-001i-9100000000-be9a96b507fb4c6e4e62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-4-Hydroxyglutamate semialdehyde 40V, Positive-QTOF	splash10-001u-9000000000-a50a3005088f974da1e6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arginine and proline metabolism	Not Available
Prolidase Deficiency (PD)		Not Available
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)		Not Available
Hyperprolinemia Type II		Not Available
Hyperprolinemia Type I		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

4HGLUSA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:: ALDH4A1
Uniprot ID:: P30038
Molecular weight:: 55117.24

Reactions

4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Water	details

Enzyme Details

2. Proline dehydrogenase 1, mitochondrial

General function:: Involved in proline dehydrogenase activity
Specific function:: Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:: PRODH
Uniprot ID:: O43272
Molecular weight:: 56196.675

Reactions

4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion → L-4-Hydroxyglutamate semialdehyde + NAD + Water	details

Showing metabocard for L-4-Hydroxyglutamate semialdehyde (HMDB0006556)

MOL for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

3D MOL for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

3D SDF for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

3D-SDF for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

PDB for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

3D PDB for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

SMILES for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

INCHI for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

Structure for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

3D Structure for HMDB0006556 (L-4-Hydroxyglutamate semialdehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions