Milk Composition Database: Showing metabocard for Pelargonic acid (BMDB0000847)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:27 UTC

Update Date

2020-06-04 19:32:21 UTC

MCDB ID

BMDB0000847

Secondary Accession Numbers

BMDB00847

Metabolite Identification

Common Name

Pelargonic acid

Description

Nonanoic acid, also known as pelargon or nonanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Nonanoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Nonanoic acid exists in all living species, ranging from bacteria to humans. Nonanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Nonanoic acid	ChEBI
1-Octanecarboxylic acid	ChEBI
CH3-[CH2]7-COOH	ChEBI
N-Nonanoic acid	ChEBI
Nonanoate	ChEBI
Nonansaeure	ChEBI
Nonoic acid	ChEBI
Nonylic acid	ChEBI
Pelargic acid	ChEBI
Pelargon	ChEBI
Pelargonsaeure	ChEBI
Pergonic acid	ChEBI
1-Nonanoate	Generator
1-Octanecarboxylate	Generator
N-Nonanoate	Generator
Nonanoic acid	Generator
Nonoate	Generator
Nonylate	Generator
Pelargate	Generator
Pergonate	Generator
Pelargonate	Generator
Cirrasol 185a	HMDB
Emery 1202	HMDB
Emery'S L-114	HMDB
Emfac 1202	HMDB
Hexacid C-9	HMDB
N-Nonoate	HMDB
N-Nonoic acid	HMDB
N-Nonylate	HMDB
N-Nonylic acid	HMDB
N-Pelargonate	HMDB
N-Pelargonic acid	HMDB
Pelargonic acid, calcium salt	HMDB
Potassium nonanoate	HMDB
Pelargonic acid, cadmium salt	HMDB
Pelargonic acid, sodium salt	HMDB
Pelargonic acid, zinc salt	HMDB
Pelargonic acid, aluminum salt	HMDB
Pelargonic acid, potassium salt	HMDB
FA(9:0)	HMDB
Pelargonic acid	ChEBI

Chemical Formula

C₉H₁₈O₂

Average Molecular Weight

158.238

Monoisotopic Molecular Weight

158.13067982

IUPAC Name

nonanoic acid

Traditional Name

nonanoic acid

CAS Registry Number

112-05-0

SMILES

CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)

InChI Key

FBUKVWPVBMHYJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:29019 )
straight-chain saturated fatty acid (CHEBI:29019 )
Straight chain fatty acids (C01601 )
Straight chain fatty acids (LMFA01010009 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	12.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 mg/mL	Not Available
LogP	3.42	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	3.47	ALOGPS
logP	3.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	44.88 m³·mol⁻¹	ChemAxon
Polarizability	19.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0910000000-29827f2f9240f991b625	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-014i-2920000000-8730f6690cd20a58fcfc	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9200000000-0842bd1d3fcea3f9f005	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08ml-9000000000-f9b45b786372be8b75d6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-0930000000-30578d3edfa20cedf0e8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-29827f2f9240f991b625	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2920000000-8730f6690cd20a58fcfc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-2e292fa3a6e414ce582a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-059f-9100000000-aaba2a9436e55f8d4c46	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06du-9200000000-bffc58a95ef321200ab9	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0k9l-9400000000-fb4f24d4e9b0b4685763	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-a3d26c56923a3cdddf9c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-a6e0c758ef2e822a5d73	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-03di-9200000000-0842bd1d3fcea3f9f005	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-08ml-9000000000-141c2435131c4b235390	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0900000000-2ea046a2e7b029c3cd81	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-1efff6d47779ec04f434	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-6900000000-bcf3e35c2fbd86e670f0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-056r-9000000000-9c72ae1d7f8e978ec7f8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-c052a9b360e11f6a6eb9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-2ea046a2e7b029c3cd81	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-1efff6d47779ec04f434	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-6900000000-bcf3e35c2fbd86e670f0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9000000000-9c72ae1d7f8e978ec7f8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-c052a9b360e11f6a6eb9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0a4i-0900000000-b56762cc671f243abe6f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9000000000-ae54c10a9e1b7264831e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9500000000-65dcbde71c36004a3676	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8ddcc5d65e84f9048b88	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-2b95d53127d2c88c6b0c	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06r6-6900000000-e3f666b3dcf9b3b1c2fe	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-8432ab96716adadb8d13	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-32f3915adea9c27b0b74	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1900000000-2ffdf4f1d36a54e86be1	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-647e33e0c7198b77f78b	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-08ml-9000000000-e02b73fd7a397aa0b40b	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	0.251 +/- 0.001 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.468 +/- 0.012 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.568 +/- 0.014 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.64 +/- 0.02 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000847

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Nonanoic_acid

METLIN ID

5810

PubChem Compound

8158

PDB ID

Not Available

ChEBI ID

29019

References

Synthesis Reference

Yu, Zhongjiang; Wang, Jinglin; Shi, Zhiming. Industrial process for producing azelaic acid and nonanoic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]

Showing metabocard for Pelargonic acid (BMDB0000847)

Structure for BMDB0000847 (Pelargonic acid)