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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 21:36:15 UTC

Update Date

2023-02-21 17:16:42 UTC

HMDB ID

HMDB0003470

Secondary Accession Numbers

HMDB03470

Metabolite Identification

Common Name

N-Formyl-L-glutamic acid

Description

N-Formyl-L-glutamic acid, also known as N-formylglutamate, ion(2-) or N-formyl-L-glutamate, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. In humans, N-formyl-L-glutamic acid is involved in the folate malabsorption, hereditary pathway. N-Formyl-L-glutamic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-formyl-L-glutamic acid a potential biomarker for the consumption of these foods. N-Formyl-L-glutamic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on N-Formyl-L-glutamic acid.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.877 -16.423   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.211 -16.423   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.877 -14.883   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      22.210 -17.193   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      26.211 -14.883   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.544 -16.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.878 -17.193   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      27.545 -17.193   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      19.543 -17.193   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      24.878 -18.733   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      23.544 -19.503   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      22.210 -18.733   0.000  0.00  0.00           O+0
CONECT    1    3    4    9                                                  
CONECT    2    7    5    8                                                  
CONECT    3    1                                                            
CONECT    4    1    6                                                       
CONECT    5    2                                                            
CONECT    6    4    7                                                       
CONECT    7    2    6   10                                                  
CONECT    8    2                                                            
CONECT    9    1                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-(Formylamino)pentanedioic acid	ChEBI
N-Formyl-L-glutamate	ChEBI
(2S)-2-(Formylamino)pentanedioate	Generator
N-Formylglutamate, ion(2-)	MeSH
N-Formylglutamate	MeSH
(2S)-2-Formamidopentanedioate	HMDB
(2S)-2-Formamidopentanedioic acid	HMDB

Chemical Formula

C₆H₉NO₅

Average Molecular Weight

175.1394

Monoisotopic Molecular Weight

175.048072403

IUPAC Name

(2S)-2-formamidopentanedioic acid

Traditional Name

N-formyl-L-glutamic acid

CAS Registry Number

1681-96-5

SMILES

OC(=O)CC[C@H](NC=O)C(O)=O

InChI Identifier

InChI=1S/C6H9NO5/c8-3-7-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1

InChI Key

ADZLWSMFHHHOBV-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-l-alpha-amino acid
N-formyl-alpha-amino acid
N-formyl-alpha amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acyl-L-glutamic acid (CHEBI:48309 )
N-formyl amino acid (CHEBI:48309 )

Ontology

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	24.5 g/L	ALOGPS
logP	-0.86	ALOGPS
logP	-1.2	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.24 m³·mol⁻¹	ChemAxon
Polarizability	15.42 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]+	140.618	31661259
DarkChem	[M-H]-	135.809	31661259
DeepCCS	[M+H]+	132.62	30932474
DeepCCS	[M-H]-	128.792	30932474
DeepCCS	[M-2H]-	166.241	30932474
DeepCCS	[M+Na]+	141.78	30932474
AllCCS	[M+H]+	138.8	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	133.9	32859911
AllCCS	[M+HCOO]-	135.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4906 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	347.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	577.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	48.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	224.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	734.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	588.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	788.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	665.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	324.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	440.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Formyl-L-glutamic acid	OC(=O)CC[C@H](NC=O)C(O)=O	2694.2	Standard polar	33892256
N-Formyl-L-glutamic acid	OC(=O)CC[C@H](NC=O)C(O)=O	1437.5	Standard non polar	33892256
N-Formyl-L-glutamic acid	OC(=O)CC[C@H](NC=O)C(O)=O	1813.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Formyl-L-glutamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](NC=O)C(=O)O	1654.9	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)NC=O	1641.2	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,1TMS,isomer #3	C[Si](C)(C)N(C=O)[C@@H](CCC(=O)O)C(=O)O	1722.2	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](NC=O)C(=O)O[Si](C)(C)C	1715.7	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N(C=O)[Si](C)(C)C	1761.5	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N(C=O)[Si](C)(C)C	1769.8	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C	1789.3	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C	1770.0	Standard non polar	33892256
N-Formyl-L-glutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=O)[Si](C)(C)C	2015.7	Standard polar	33892256
N-Formyl-L-glutamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](NC=O)C(=O)O	1905.3	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)NC=O	1874.2	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=O)[C@@H](CCC(=O)O)C(=O)O	1945.1	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](NC=O)C(=O)O[Si](C)(C)C(C)(C)C	2131.7	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N(C=O)[Si](C)(C)C(C)(C)C	2212.3	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N(C=O)[Si](C)(C)C(C)(C)C	2192.8	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C	2406.2	Semi standard non polar	33892256
N-Formyl-L-glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C	2386.1	Standard non polar	33892256
N-Formyl-L-glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C=O)[Si](C)(C)C(C)(C)C	2367.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
One carbon pool by folate	Not Available
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)		Not Available
Methotrexate Action Pathway		Not Available
Folate malabsorption, hereditary		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

FDB023180

KNApSAcK ID

Not Available

Chemspider ID

388496

KEGG Compound ID

C01045

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6939

PubChem Compound

439376

PDB ID

Not Available

ChEBI ID

48309

Food Biomarker Ontology

Not Available

VMH ID

NFORGLU

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Borek, Blanche Ann; Waelsch, Heinrich. The enzymic degradation of histidine. Journal of Biological Chemistry (1953), 205 459-74.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Formimidoyltransferase-cyclodeaminase

General function:: Involved in catalytic activity
Specific function:: Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:: FTCD
Uniprot ID:: O95954
Molecular weight:: 58925.93

Reactions

Folinic acid + Glutamic acid → Tetrahydrofolic acid + N-Formyl-L-glutamic acid	details
Folinic acid + Glutamic acid → Tetrahydrofolic acid + N-Formyl-L-glutamic acid	details

Showing metabocard for N-Formyl-L-glutamic acid (HMDB0003470)

MOL for HMDB0003470 (N-Formyl-L-glutamic acid)

3D MOL for HMDB0003470 (N-Formyl-L-glutamic acid)

3D SDF for HMDB0003470 (N-Formyl-L-glutamic acid)

3D-SDF for HMDB0003470 (N-Formyl-L-glutamic acid)

PDB for HMDB0003470 (N-Formyl-L-glutamic acid)

3D PDB for HMDB0003470 (N-Formyl-L-glutamic acid)

SMILES for HMDB0003470 (N-Formyl-L-glutamic acid)

INCHI for HMDB0003470 (N-Formyl-L-glutamic acid)

Structure for HMDB0003470 (N-Formyl-L-glutamic acid)

3D Structure for HMDB0003470 (N-Formyl-L-glutamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions