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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:38:37 UTC

Update Date

2023-02-21 17:23:43 UTC

HMDB ID

HMDB0033870

Secondary Accession Numbers

HMDB33870

Metabolite Identification

Common Name

Butyramide

Description

Butyramide, also known as C3H7C(O)NH2 or N-butanamide, belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, butyramide is considered to be a fatty amide. Based on a literature review a significant number of articles have been published on Butyramide.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Butanoic acid, amide	ChEBI
Butyramid	ChEBI
Butyrylamide	ChEBI
C3H7C(O)NH2	ChEBI
N-Butanamide	ChEBI
N-Butylamide	ChEBI
N-Butyramide	ChEBI
N-C3H7C(O)NH2	ChEBI
Butanoate, amide	Generator
Butanamide	HMDB
Butanimidic acid	HMDB

Chemical Formula

C₄H₉NO

Average Molecular Weight

87.1204

Monoisotopic Molecular Weight

87.068413915

IUPAC Name

butanamide

Traditional Name

butyramide

CAS Registry Number

541-35-5

SMILES

CCCC(O)=N

InChI Identifier

InChI=1S/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6)

InChI Key

DNSISZSEWVHGLH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butanamides (CHEBI:50724 )
a small molecule (BUTYRAMIDE )

Ontology

Physiological effect

Organoleptic effect

Odor

Nutty

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033870)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033870)

Source

Exogenous

Exogenous (HMDB: HMDB0033870)

Food

Food (HMDB: HMDB0033870)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033870)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033870)

Lipid metabolism pathway (HMDB: HMDB0033870)

Biochemical process

Lipid transport (HMDB: HMDB0033870)

Role

Biological role

Energy source (HMDB: HMDB0033870)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0033870)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	115 - 116 °C	Not Available
Boiling Point	216.00 to 217.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	163 mg/mL at 15 °C	Not Available
LogP	-0.21	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	216 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	0.11	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	16.96	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.69 m³·mol⁻¹	ChemAxon
Polarizability	9.61 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]+	116.235	31661259
DarkChem	[M-H]-	111.401	31661259
DeepCCS	[M+H]+	127.655	30932474
DeepCCS	[M-H]-	125.8	30932474
DeepCCS	[M-2H]-	161.153	30932474
DeepCCS	[M+Na]+	135.165	30932474
AllCCS	[M+H]+	123.2	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	127.4	32859911
AllCCS	[M+Na]+	128.6	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	132.2	32859911
AllCCS	[M+HCOO]-	137.3	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.	1.75 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3992 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.25 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyramide	CCCC(N)=O	1848.3	Standard polar	33892256
Butyramide	CCCC(N)=O	839.3	Standard non polar	33892256
Butyramide	CCCC(N)=O	928.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butyramide,1TMS,isomer #1	CCCC(=O)N[Si](C)(C)C	1025.2	Semi standard non polar	33892256
Butyramide,1TMS,isomer #1	CCCC(=O)N[Si](C)(C)C	1042.6	Standard non polar	33892256
Butyramide,2TMS,isomer #1	CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1197.5	Semi standard non polar	33892256
Butyramide,2TMS,isomer #1	CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1148.6	Standard non polar	33892256
Butyramide,1TBDMS,isomer #1	CCCC(=O)N[Si](C)(C)C(C)(C)C	1256.7	Semi standard non polar	33892256
Butyramide,1TBDMS,isomer #1	CCCC(=O)N[Si](C)(C)C(C)(C)C	1219.6	Standard non polar	33892256
Butyramide,2TBDMS,isomer #1	CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1604.3	Semi standard non polar	33892256
Butyramide,2TBDMS,isomer #1	CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1558.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Butyramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-0a7a584657b22254012b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyramide 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 - Butyramide 10V, Positive-QTOF	splash10-0079-9000000000-0eca6ad6056e9d99a12e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 20V, Positive-QTOF	splash10-00di-9000000000-8d19ba5c849dd71e9f55	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 40V, Positive-QTOF	splash10-0006-9000000000-5d9ed5fdd5f033d01d27	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 10V, Negative-QTOF	splash10-000i-9000000000-8eaa392a1fd75490f0db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 20V, Negative-QTOF	splash10-000l-9000000000-3a0d3ac9af6de2874568	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 40V, Negative-QTOF	splash10-0006-9000000000-76f7e3debe07de7cbcf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 10V, Positive-QTOF	splash10-0079-9000000000-64c195eaa3ea3d1f608a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 20V, Positive-QTOF	splash10-0006-9000000000-f36a9ace843ae2e9f73c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 40V, Positive-QTOF	splash10-0006-9000000000-00dbcef465bf69423cf0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 10V, Negative-QTOF	splash10-000i-9000000000-cac7a5f55f0489e13d41	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 20V, Negative-QTOF	splash10-000f-9000000000-d2789779a3587ef6a706	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyramide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

DB02121

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012058

KNApSAcK ID

C00043175

Chemspider ID

10464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butanamide

METLIN ID

Not Available

PubChem Compound

10927

PDB ID

BMD

ChEBI ID

50724

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583981

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Butyramide (HMDB0033870)

MOL for HMDB0033870 (Butyramide)

3D MOL for HMDB0033870 (Butyramide)

3D SDF for HMDB0033870 (Butyramide)

3D-SDF for HMDB0033870 (Butyramide)

PDB for HMDB0033870 (Butyramide)

3D PDB for HMDB0033870 (Butyramide)

SMILES for HMDB0033870 (Butyramide)

INCHI for HMDB0033870 (Butyramide)

Structure for HMDB0033870 (Butyramide)

3D Structure for HMDB0033870 (Butyramide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra