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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:37 UTC

Update Date

2023-02-21 17:19:36 UTC

HMDB ID

HMDB0030409

Secondary Accession Numbers

HMDB30409

Metabolite Identification

Common Name

4-Amino-2-methylenebutanoic acid

Description

4-Amino-2-methylenebutanoic 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. Based on a literature review very few articles have been published on 4-Amino-2-methylenebutanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Amino-2-methylenebutanoate	Generator
g-Amino-a-methylenebutyric acid	HMDB
4-Amino-2-methylidenebutanoate	HMDB

Chemical Formula

C₅H₉NO₂

Average Molecular Weight

115.1305

Monoisotopic Molecular Weight

115.063328537

IUPAC Name

4-amino-2-methylidenebutanoic acid

Traditional Name

4-amino-2-methylidenebutanoic acid

CAS Registry Number

65370-67-4

SMILES

NCCC(=C)C(O)=O

InChI Identifier

InChI=1S/C5H9NO2/c1-4(2-3-6)5(7)8/h1-3,6H2,(H,7,8)

InChI Key

FTWHFXMUJQRNBK-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
Amino fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030409)
Cytoplasm (HMDB: HMDB0030409)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030409)

Source

Endogenous

Endogenous (HMDB: HMDB0030409)

Plant

Plant (HMDB: HMDB0030409)

Exogenous

Food

Food (HMDB: HMDB0030409)

Nut

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 - 179 °C	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	164 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.4	ChemAxon
logS	0.15	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	10.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.84 m³·mol⁻¹	ChemAxon
Polarizability	11.65 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]+	123.342	31661259
DarkChem	[M-H]-	118.163	31661259
DeepCCS	[M+H]+	126.058	30932474
DeepCCS	[M-H]-	123.258	30932474
DeepCCS	[M-2H]-	159.561	30932474
DeepCCS	[M+Na]+	134.169	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-2-methylenebutanoic acid	NCCC(=C)C(O)=O	2014.9	Standard polar	33892256
4-Amino-2-methylenebutanoic acid	NCCC(=C)C(O)=O	1216.7	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid	NCCC(=C)C(O)=O	1143.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-2-methylenebutanoic acid,1TMS,isomer #1	C=C(CCN)C(=O)O[Si](C)(C)C	1188.5	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,1TMS,isomer #2	C=C(CCN[Si](C)(C)C)C(=O)O	1311.9	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #1	C=C(CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C	1353.0	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #1	C=C(CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C	1432.2	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #2	C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1530.8	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #2	C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1445.3	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid,3TMS,isomer #1	C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1545.6	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,3TMS,isomer #1	C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1557.4	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid,1TBDMS,isomer #1	C=C(CCN)C(=O)O[Si](C)(C)C(C)(C)C	1402.8	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,1TBDMS,isomer #2	C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O	1560.4	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #1	C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1798.1	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #1	C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1811.9	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #2	C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	1962.8	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #2	C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	1865.6	Standard non polar	33892256
4-Amino-2-methylenebutanoic acid,3TBDMS,isomer #1	C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2190.4	Semi standard non polar	33892256
4-Amino-2-methylenebutanoic acid,3TBDMS,isomer #1	C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2155.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-5bce7376b76e0e5d734d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9200000000-06aae0df20cb65cf4e95	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 4-Amino-2-methylenebutanoic acid 10V, Positive-QTOF	splash10-00kb-9300000000-87bbc6affbd5953b1b4a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Positive-QTOF	splash10-0f6t-9000000000-12225cc8d658dc7e9857	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Positive-QTOF	splash10-0udi-9000000000-86ded6c35c43a4b0ab47	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Negative-QTOF	splash10-03di-2900000000-69900af268e52fa5ad18	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Negative-QTOF	splash10-0229-9400000000-518b22bf53e4ba0abdb2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Negative-QTOF	splash10-0v4l-9000000000-1edce3c9adc88aaede62	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Positive-QTOF	splash10-0002-9100000000-ff1346c48908fbea1510	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Positive-QTOF	splash10-0fdo-9000000000-efbda9f06b3632d2fc21	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Positive-QTOF	splash10-0zfu-9000000000-2521a990ed07185cccfa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Negative-QTOF	splash10-01ot-9500000000-cfef122a5cd40b6ef7c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Negative-QTOF	splash10-00kb-9000000000-cee8ead2149daee5efed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Negative-QTOF	splash10-0gb9-9000000000-5bfd61203c81eb2c616b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB002271

KNApSAcK ID

C00054452

Chemspider ID

4476652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318003

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Amino-2-methylenebutanoic acid (HMDB0030409)

MOL for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

3D MOL for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

3D SDF for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

3D-SDF for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

PDB for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

3D PDB for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

SMILES for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

INCHI for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

Structure for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

3D Structure for HMDB0030409 (4-Amino-2-methylenebutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra