MiMeDB: Showing metabocard for Formiminoglutamic acid (MMDBc0000371)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:19 UTC

Update Date

2022-08-31 06:02:45 UTC

Metabolite ID

MMDBc0000371

Metabolite Identification

Common Name

Formiminoglutamic acid

Description

Formiminoglutamic acid, also known as N-formimino-L-glutamate or formimino-glu, 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. Formiminoglutamic acid exists in all living organisms, ranging from bacteria to humans. In humans, formiminoglutamic acid is involved in the histidine metabolism pathway. Formiminoglutamic 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 formiminoglutamic acid a potential biomarker for the consumption of these foods. Formiminoglutamic 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 a significant number of articles have been published on Formiminoglutamic 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      19.116 -11.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.659 -11.346   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      18.459 -13.008   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.836 -10.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.423 -10.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.414 -14.217   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.822  -8.806   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.457 -11.176   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.957 -10.009   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      18.840 -15.647   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      23.807 -11.417   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      23.722  -8.665   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5   11   12                                                  
CONECT   10    6                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
N-Formimidoyl-L-glutamate	ChEBI
N-Formimino-L-glutamate	ChEBI
N-Formimidoyl-L-glutamic acid	Generator
N-Formimino-L-glutamic acid	Generator
Formiminoglutamate	Generator
Formimino-glu	HMDB
Formimino-L-glutamate	HMDB
Formimino-L-glutamic acid	HMDB
N-(Iminomethyl)-L-glutamic acid	HMDB
N-Formimidoyl-glutamic acid	HMDB
N-Formimino-glutamate	HMDB
Acid, formiminoglutamic	HMDB
FIGLU	HMDB

Molecular Formula

C₆H₁₀N₂O₄

Average Mass

174.1546

Monoisotopic Mass

174.064056818

IUPAC Name

(2S)-2-methanimidamidopentanedioic acid

Traditional Name

N-formimino-L-glutamate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1

InChI Key

NRXIKWMTVXPVEF-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
Dicarboxylic acid or derivatives
Fatty acid
Amidine
Carboxylic acid amidine
Carboxylic acid
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Formamidine
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:7274 )
L-glutamic acid derivative (CHEBI:7274 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.28 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	10.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	110.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	48.71 m³·mol⁻¹	ChemAxon
Polarizability	15.61 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	splash10-056u-9400000000-6cceb3db80c1c51b5798	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fg9-9230000000-65123e05e539b5af2388	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-92c0f47c419298fb78a2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-5900000000-8b915dd10756167a4003	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0012-9100000000-313b0983e834934e5682	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-b264a846efb94105ac49	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f97-5900000000-2f4ec838a8ef46f9428d	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9200000000-a518077a6ec2f6a6c6c5	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-e21825a4085307dba501	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02d0-7900000000-39bddd8ed9efae999a7c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0015-9000000000-8230ed13a5a7ee4c82a6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0900000000-d26547339916cbc25d34	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0773-9700000000-d2b6c121d8ab7a8500b7	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-abb21e9862307446d7ec	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Urine

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
MMDBp0192325	Formimidoyltransferase-cyclodeaminase	Enzyme	O95954	Homo sapiens
MMDBp0195441	Probable imidazolonepropionase	Unknown	Q96NU7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001339	Formiminoglutamic acid	5-Formiminotetrahydrofolic acid	Not Available	Glutamate Formimidoyltransferase	VMH	30371894
MMDBr0006025	Formiminoglutamic acid	Formiminoglutamic acid	Not Available	Transport of N-Formimidoyl-L-Glutamate	VMH	30371894
MMDBr0006934	Formiminoglutamic acid	Formamide	Not Available	Formimidoylglutamase	VMH	30371894
MMDBr0006943	5-Formiminotetrahydrofolic acid	Formiminoglutamic acid	Not Available	Glutamate formiminotransferase (EC 2.1.2.5) @ Glutamate formyltransferase	VMH	30371894
MMDBr0007881	4-Imidazolone-5-propionic acid	Formiminoglutamic acid	Not Available	Imidazolonepropionase	VMH	30371894
MMDBr0008497	Formiminoglutamic acid	N-Formyl-L-glutamate	Not Available	N-Formimino-L-glutamate iminohydrolase	VMH	30371894
MMDBr0010755	Folinic acid	Formiminoglutamic acid	Formimidoyltransferase cyclodeaminase	5-Formyltetrahydrofolate:L-Glutamate N-Formiminotransferase	VMH	30371894
MMDBr0013388	5-formimidoyltetrahydrofolic acid	(6S)-5,6,7,8-tetrahydrofolic acid	Glutamate formimidoyltransferase	Transfer of a formimidoyl group	RHEA	34755880
MMDBr0014217	Water	Formamide	Formimidoylglutamase	Hydrolysis of carbon-nitrogen bond	RHEA	34755880
MMDBr0014365	4-Imidazolone-5-propionic acid	Formiminoglutamic acid	Imidazolonepropionase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880

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
Bacteria	Firmicutes	297	Human feces; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Cattle ; Human stool; Human mucosa; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	103	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	306	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; River trout ; Sheep	Metabolic reconstruction
Bacteria	Bacteroidetes	121	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	2	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	6		Metabolic reconstruction
Bacteria/NULL	Proteobacteria	2	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; River trout ; Sheep	Metabolic reconstruction
Bacteria	Chloroflexi	2
Bacteria	Deinococcus-thermus	2
Bacteria	Thermotogae	1
Archaea/Archaea	Crenarchaeota	1
Bacteria	Acidobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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 Urine	Detected and Quantified			780.114	1876.796	umol/mmol creatinine	Children (1-13 years old)	Both	Glutamate formiminotransferase deficiency	HMDB	235753
Human Urine	Detected and Quantified	0.90	0.71			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified			13.400	21.800	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	235753
Human Urine	Detected and Quantified	0.47		0.0	0.80	umol/mmol creatinine	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 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	29808030

External Links

HMDB ID

HMDB0000854

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022280

KNApSAcK ID

Not Available

Chemspider ID

388370

KEGG Compound ID

C00439

BioCyc ID

N-FORMIMINO-L-GLUTAMATE

BiGG ID

34986

Wikipedia Link

Formiminoglutamic acid

METLIN ID

5817

PubChem Compound

439233

PDB ID

Not Available

ChEBI ID

7274

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. doi: 10.1203/00006450-197503000-00001. [PubMed:235753 ]
Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. doi: 10.1172/JCI109580. [PubMed:500809 ]
Verhoeven NM, Wanders RJ, Poll-The BT, Saudubray JM, Jakobs C: The metabolism of phytanic acid and pristanic acid in man: a review. J Inherit Metab Dis. 1998 Oct;21(7):697-728. doi: 10.1023/a:1005476631419. [PubMed:9819701 ]
Hilton JF, Christensen KE, Watkins D, Raby BA, Renaud Y, de la Luna S, Estivill X, MacKenzie RE, Hudson TJ, Rosenblatt DS: The molecular basis of glutamate formiminotransferase deficiency. Hum Mutat. 2003 Jul;22(1):67-73. doi: 10.1002/humu.10236. [PubMed:12815595 ]

Showing metabocard for Formiminoglutamic acid (MMDBc0000371)

MOL for #<Metabolite:0x00007f5a9481f628>

3D MOL for #<Metabolite:0x00007f5a9481f628>

3D SDF for #<Metabolite:0x00007f5a9481f628>

3D-SDF for #<Metabolite:0x00007f5a9481f628>

PDB for #<Metabolite:0x00007f5a9481f628>

3D PDB for #<Metabolite:0x00007f5a9481f628>

SMILES for #<Metabolite:0x00007f5a9481f628>

INCHI for #<Metabolite:0x00007f5a9481f628>

Structure for #<Metabolite:0x00007f5a9481f628>

3D Structure for #<Metabolite:0x00007f5a9481f628>