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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:41 UTC

Update Date

2023-02-21 17:16:15 UTC

HMDB ID

HMDB0002201

Secondary Accession Numbers

HMDB02201

Metabolite Identification

Common Name

N-Carboxyethyl-g-aminobutyric acid

Description

N-Carboxyethyl-g-aminobutyric acid belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. N-Carboxyethyl-g-aminobutyric 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-carboxyethyl-g-aminobutyric acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Carboxyethyl-g-aminobutyric acid.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine.mol 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    4    8                                                       
CONECT    8    9    7                                                       
CONECT    9    8   10                                                       
CONECT   10   11   12    9                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
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-Carboxyethyl-g-aminobutyrate	Generator
2-Carboxyethyl gamma-aminobutyric acid	MeSH
4-(2-Carboxy-ethylamino)-butyrate	HMDB
4-(2-Carboxy-ethylamino)-butyric acid	HMDB
Carboxyethyl-gaba	HMDB
CEGABA	HMDB
N-Carboxyethyl-gamma-aminobutyrate	HMDB, Generator
N-Carboxyethyl-gamma-aminobutyric acid	HMDB
Spermidate	HMDB
Spermidic acid	HMDB
4-[(2-Carboxyethyl)amino]butanoate	Generator, HMDB
N-Carboxyethyl-g-aminobutyric acid	Generator
N-Carboxyethyl-γ-aminobutyrate	Generator, HMDB
N-Carboxyethyl-γ-aminobutyric acid	Generator, HMDB

Chemical Formula

C₇H₁₃NO₄

Average Molecular Weight

175.1824

Monoisotopic Molecular Weight

175.084457909

IUPAC Name

4-[(2-carboxyethyl)amino]butanoic acid

Traditional Name

cegaba

CAS Registry Number

4386-03-2

SMILES

OC(=O)CCCNCCC(O)=O

InChI Identifier

InChI=1S/C7H13NO4/c9-6(10)2-1-4-8-5-3-7(11)12/h8H,1-5H2,(H,9,10)(H,11,12)

InChI Key

SRGQUICKDUQCKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma 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

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Beta amino acid or derivatives
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0002201)

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

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	409.18 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.146 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.9 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	10.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	41.02 m³·mol⁻¹	ChemAxon
Polarizability	17.84 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]+	139.48	31661259
DarkChem	[M-H]-	134.173	31661259
DeepCCS	[M+H]+	134.802	30932474
DeepCCS	[M-H]-	131.064	30932474
DeepCCS	[M-2H]-	167.905	30932474
DeepCCS	[M+Na]+	143.367	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	142.1	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.	1.8 minutes	32390414
Predicted by Siyang on May 30, 2022	8.5472 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	358.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	404.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	255.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	56.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	263.0 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	228.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	790.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	538.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.1 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	654.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	818.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	469.3 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	385.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Carboxyethyl-g-aminobutyric acid	OC(=O)CCCNCCC(O)=O	2694.8	Standard polar	33892256
N-Carboxyethyl-g-aminobutyric acid	OC(=O)CCCNCCC(O)=O	1590.4	Standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid	OC(=O)CCCNCCC(O)=O	1626.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Carboxyethyl-g-aminobutyric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCNCCC(=O)O	1688.0	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCNCCCC(=O)O	1695.6	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,1TMS,isomer #3	C[Si](C)(C)N(CCCC(=O)O)CCC(=O)O	1806.7	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCNCCC(=O)O[Si](C)(C)C	1787.7	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCN(CCC(=O)O)[Si](C)(C)C	1863.8	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CCN(CCCC(=O)O)[Si](C)(C)C	1862.2	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1871.5	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1873.4	Standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	1969.6	Standard polar	33892256
N-Carboxyethyl-g-aminobutyric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCNCCC(=O)O	1947.5	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCNCCCC(=O)O	1955.0	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCC(=O)O)CCC(=O)O	2015.8	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCNCCC(=O)O[Si](C)(C)C(C)(C)C	2237.3	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCN(CCC(=O)O)[Si](C)(C)C(C)(C)C	2334.7	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCN(CCCC(=O)O)[Si](C)(C)C(C)(C)C	2339.4	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2557.8	Semi standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2462.0	Standard non polar	33892256
N-Carboxyethyl-g-aminobutyric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCN(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2348.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

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
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB022902

KNApSAcK ID

Not Available

Chemspider ID

2474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6542

PubChem Compound

2572

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1359021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Fussi F, Savoldi F, Curti M: Identification of N-carboxyethyl gamma-aminobutyric acid in bovine brain and human cerebrospinal fluid. Neurosci Lett. 1987 Jun 26;77(3):308-10. [PubMed:3614763 ]

Showing metabocard for N-Carboxyethyl-g-aminobutyric acid (HMDB0002201)

MOL for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

3D MOL for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

3D SDF for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

3D-SDF for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

PDB for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

3D PDB for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

SMILES for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

INCHI for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

Structure for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

3D Structure for HMDB0002201 (N-Carboxyethyl-g-aminobutyric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized