Jump To Section:

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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:14 UTC

HMDB ID

HMDB0000854

Secondary Accession Numbers

HMDB00854

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₆H₁₀N₂O₄

Average Molecular Weight

174.1546

Monoisotopic Molecular Weight

174.064056818

IUPAC Name

(2S)-2-methanimidamidopentanedioic acid

Traditional Name

N-formimino-L-glutamate

CAS Registry Number

816-90-0

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 )

Ontology

Not Available

Urine (PMID: 2026685)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0000854)

Source

Endogenous

Endogenous (HMDB: HMDB0000854)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Histidine Metabolism (PathBank: SMP0063632)
Histidine Metabolism (HMDB: HMDB0000854)

Disease pathway

Histidinemia (PathBank: SMP0120493)

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	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.944	31661259
DarkChem	[M-H]-	136.031	31661259
AllCCS	[M+H]+	139.239	32859911
AllCCS	[M-H]-	133.325	32859911
DeepCCS	[M+H]+	133.424	30932474
DeepCCS	[M-H]-	129.633	30932474
DeepCCS	[M-2H]-	167.121	30932474
DeepCCS	[M+Na]+	142.66	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	135.4	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	133.3	32859911
AllCCS	[M+Na-2H]-	134.8	32859911
AllCCS	[M+HCOO]-	136.5	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.	0.32 minutes	32390414
Predicted by Siyang on May 30, 2022	9.641 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	421.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	446.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	312.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	34.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	303.8 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	220.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	876.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	593.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.6 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	670.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	297.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	772.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	481.7 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	481.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Formiminoglutamic acid	OC(=O)CC[C@H](NC=N)C(O)=O	2967.9	Standard polar	33892256
Formiminoglutamic acid	OC(=O)CC[C@H](NC=N)C(O)=O	1605.3	Standard non polar	33892256
Formiminoglutamic acid	OC(=O)CC[C@H](NC=N)C(O)=O	1882.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Formiminoglutamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](NC=N)C(=O)O	1801.7	Semi standard non polar	33892256
Formiminoglutamic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)NC=N	1762.5	Semi standard non polar	33892256
Formiminoglutamic acid,1TMS,isomer #3	C[Si](C)(C)N(C=N)[C@@H](CCC(=O)O)C(=O)O	1875.6	Semi standard non polar	33892256
Formiminoglutamic acid,1TMS,isomer #4	C[Si](C)(C)N=CN[C@@H](CCC(=O)O)C(=O)O	1813.9	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](NC=N)C(=O)O[Si](C)(C)C	1821.6	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N(C=N)[Si](C)(C)C	1904.4	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #3	C[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1818.3	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N(C=N)[Si](C)(C)C	1903.3	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #5	C[Si](C)(C)N=CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1815.7	Semi standard non polar	33892256
Formiminoglutamic acid,2TMS,isomer #6	C[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1910.8	Semi standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=N)[Si](C)(C)C	1911.4	Semi standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=N)[Si](C)(C)C	1840.3	Standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N(C=N)[Si](C)(C)C	2412.8	Standard polar	33892256
Formiminoglutamic acid,3TMS,isomer #2	C[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1849.1	Semi standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #2	C[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1683.3	Standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #2	C[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2671.5	Standard polar	33892256
Formiminoglutamic acid,3TMS,isomer #3	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1901.7	Semi standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #3	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1879.7	Standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #3	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2487.8	Standard polar	33892256
Formiminoglutamic acid,3TMS,isomer #4	C[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1920.8	Semi standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #4	C[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1855.2	Standard non polar	33892256
Formiminoglutamic acid,3TMS,isomer #4	C[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2473.5	Standard polar	33892256
Formiminoglutamic acid,4TMS,isomer #1	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1931.2	Semi standard non polar	33892256
Formiminoglutamic acid,4TMS,isomer #1	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1860.7	Standard non polar	33892256
Formiminoglutamic acid,4TMS,isomer #1	C[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2236.6	Standard polar	33892256
Formiminoglutamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](NC=N)C(=O)O	2054.0	Semi standard non polar	33892256
Formiminoglutamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)NC=N	2029.1	Semi standard non polar	33892256
Formiminoglutamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=N)[C@@H](CCC(=O)O)C(=O)O	2098.6	Semi standard non polar	33892256
Formiminoglutamic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O)C(=O)O	2060.5	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](NC=N)C(=O)O[Si](C)(C)C(C)(C)C	2253.9	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N(C=N)[Si](C)(C)C(C)(C)C	2369.1	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2268.2	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N(C=N)[Si](C)(C)C(C)(C)C	2348.3	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2246.1	Semi standard non polar	33892256
Formiminoglutamic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2309.9	Semi standard non polar	33892256
Formiminoglutamic 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=N)[Si](C)(C)C(C)(C)C	2544.5	Semi standard non polar	33892256
Formiminoglutamic 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=N)[Si](C)(C)C(C)(C)C	2460.0	Standard non polar	33892256
Formiminoglutamic 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=N)[Si](C)(C)C(C)(C)C	2624.8	Standard polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2449.9	Semi standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2280.4	Standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=CN[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2721.0	Standard polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2539.5	Semi standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2379.9	Standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2671.2	Standard polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2535.2	Semi standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2366.3	Standard non polar	33892256
Formiminoglutamic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2662.3	Standard polar	33892256
Formiminoglutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2745.5	Semi standard non polar	33892256
Formiminoglutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2551.9	Standard non polar	33892256
Formiminoglutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=CN([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2588.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9400000000-6cceb3db80c1c51b5798	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0fg9-9230000000-65123e05e539b5af2388	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Formiminoglutamic acid GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-06	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 - Formiminoglutamic acid 10V, Positive-QTOF	splash10-056r-0900000000-92c0f47c419298fb78a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 20V, Positive-QTOF	splash10-004j-5900000000-8b915dd10756167a4003	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 40V, Positive-QTOF	splash10-0012-9100000000-313b0983e834934e5682	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 10V, Negative-QTOF	splash10-00fr-1900000000-b264a846efb94105ac49	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 20V, Negative-QTOF	splash10-0f97-5900000000-2f4ec838a8ef46f9428d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 40V, Negative-QTOF	splash10-002f-9200000000-a518077a6ec2f6a6c6c5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 10V, Positive-QTOF	splash10-004i-0900000000-e21825a4085307dba501	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 20V, Positive-QTOF	splash10-02d0-7900000000-39bddd8ed9efae999a7c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 40V, Positive-QTOF	splash10-0015-9000000000-8230ed13a5a7ee4c82a6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 10V, Negative-QTOF	splash10-00b9-0900000000-d26547339916cbc25d34	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 20V, Negative-QTOF	splash10-0773-9700000000-d2b6c121d8ab7a8500b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Formiminoglutamic acid 40V, Negative-QTOF	splash10-0006-9100000000-abb21e9862307446d7ec	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Histidine metabolism
Histidinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.47 (0.0-0.80) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.90 +/- 0.71 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	13.400-21.800 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	235753	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	780.114-1876.796 umol/mmol creatinine	Children (1-13 years old)	Both	Glutamate formiminotransferase deficiency	235753	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Glutamate formiminotransferase deficiency
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. [PubMed:235753 ]

Associated OMIM IDs

114500 (Colorectal cancer)
229100 (Glutamate formiminotransferase deficiency)

External Links

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

VMH ID

FORGLU

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Tabor, Herbert; Rabinowitz, Jesse C. Insts. Formiminoglycine, formimino-L-aspartic acid, and formimino-L-glutamic acid.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:12815595 ]
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. [PubMed:500809 ]
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. [PubMed:235753 ]
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. [PubMed:9819701 ]

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

5-Formiminotetrahydrofolic acid + Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic acid	details
5-Formiminotetrahydrofolic acid + Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic acid	details

Enzyme Details

2. Probable imidazolonepropionase

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:: Not Available
Gene Name:: AMDHD1
Uniprot ID:: Q96NU7
Molecular weight:: 46742.505

Reactions

4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Ion	details
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid	details

Showing metabocard for Formiminoglutamic acid (HMDB0000854)

MOL for HMDB0000854 (Formiminoglutamic acid)

3D MOL for HMDB0000854 (Formiminoglutamic acid)

3D SDF for HMDB0000854 (Formiminoglutamic acid)

3D-SDF for HMDB0000854 (Formiminoglutamic acid)

PDB for HMDB0000854 (Formiminoglutamic acid)

3D PDB for HMDB0000854 (Formiminoglutamic acid)

SMILES for HMDB0000854 (Formiminoglutamic acid)

INCHI for HMDB0000854 (Formiminoglutamic acid)

Structure for HMDB0000854 (Formiminoglutamic acid)

3D Structure for HMDB0000854 (Formiminoglutamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions