Milk Composition Database: Showing metabocard for 4-Acetamidobutanoic acid (BMDB0003681)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:05:51 UTC

Update Date

2020-05-11 20:49:23 UTC

MCDB ID

BMDB0003681

Secondary Accession Numbers

BMDB03681

Metabolite Identification

Common Name

4-Acetamidobutanoic acid

Description

4-Acetamidobutanoic acid, also known as N4-acetylaminobutanoate or N-acetyl-4-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. 4-Acetamidobutanoic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Acetamidobutanoic acid exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-Acetamidobutyric acid	ChEBI
N-Acetyl-4-aminobutanoic acid	ChEBI
N-Acetyl-4-aminobutyric acid	ChEBI
N4-Acetylaminobutanoic acid	ChEBI
N4-Acetylaminobutanoate	Kegg
4-Acetamidobutyrate	Generator
N-Acetyl-4-aminobutanoate	Generator
N-Acetyl-4-aminobutyrate	Generator
4-Acetamidobutanoate	Generator
4-(Acetylamino)butanoate	HMDB
4-(Acetylamino)butanoic acid	HMDB
N-Acetyl-gaba	HMDB
N-Acetyl-gamma-amino-N-butyric acid	HMDB
N-Acetyl-gamma-aminobutyrate	HMDB
4-Acetamidobutanoic acid	Generator

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.1564

Monoisotopic Molecular Weight

145.073893223

IUPAC Name

4-acetamidobutanoic acid

Traditional Name

4-acetamidobutyrate

CAS Registry Number

3025-96-5

SMILES

CC(=O)NCCCC(O)=O

InChI Identifier

InChI=1S/C6H11NO3/c1-5(8)7-4-2-3-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)

InChI Key

UZTFMUBKZQVKLK-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
Straight chain fatty acid
Fatty acid
Fatty acyl
Carboximidic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboximidic acid derivative
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:17645 )
N-acyl-amino acid (CHEBI:17645 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.48	ALOGPS
logP	-0.8	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.9 m³·mol⁻¹	ChemAxon
Polarizability	14.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0ab9-5910000000-616492abfabb6439af40	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-000i-8900000000-9c41d4816e53d2df1696	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ab9-5910000000-616492abfabb6439af40	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-8900000000-9c41d4816e53d2df1696	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ab9-5910000000-616492abfabb6439af40	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-8900000000-9c41d4816e53d2df1696	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0900000000-5bd8cc559b90a64af1a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-5910000000-392be10f3144349f0934	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-1d251bd6acc9a9656032	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9200000000-801b38a728ac351762e3	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-1900000000-2b55924041c3b349dcb9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000j-0900000000-9b0713f455b5092ea5b0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e5fde6eaebd01f451c7f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-3972b9ef14264b429520	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-9400000000-d95f6a6ba1204f161f79	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-2c0aea728a176600d0f7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9000000000-f951bf26c46355051dcd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-e7ff97e64796256818b9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0zfu-9000000000-8470fa62694d42f7cf46	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-32674c3224c62b6749b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-9000000000-52e05e0b0cc738581e02	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9400000000-fa598256216f3a773f85	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9000000000-503de5ea2b9646670b33	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d076eacb831ac2756c00	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-1900000000-7dee9dd60cf632b0bd8a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-9000000000-5fbb7042c8be53d56fcd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-6094e06c5cf1fdd7227e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-25f48ea2b441b3bed653	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0007-9000000000-bb39013f9bdb183b52b4	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-4900000000-61610846c38b08a1c362	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9300000000-34ef78b671c3a4979c55	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-979b40d7d5bb3012fba3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-2900000000-a4f5296fa5b6b4439356	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pdl-8900000000-08e05706af59b90ee5ae	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-7586f2859664a58f822d	2015-04-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	2016-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 23438684	details

External Links

HMDB ID

HMDB0003681

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023214

KNApSAcK ID

Not Available

Chemspider ID

17180

KEGG Compound ID

C02946

BioCyc ID

Not Available

BiGG ID

1446095

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18189

PDB ID

Not Available

ChEBI ID

17645

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Showing metabocard for 4-Acetamidobutanoic acid (BMDB0003681)

Structure for BMDB0003681 (4-Acetamidobutanoic acid)