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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-04-01 19:19:39 UTC
HMDB IDHMDB0000847
Secondary Accession Numbers
  • HMDB00847
Metabolite Identification
Common NamePelargonic acid
DescriptionPelargonic acid, or nonanoic acid, is a fatty acid which occurs naturally as esters is the oil of pelargonium. Synthetic esters, such as methyl nonanoate, are used as flavorings. Pelargonic acid is an organic compound composed of a nine-carbon chain terminating in a carboxylic acid. It is an oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but well soluble in chloroform and ether. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays.
Structure
Data?1547234111
Synonyms
ValueSource
1-Nonanoic acidChEBI
1-Octanecarboxylic acidChEBI
CH3-[CH2]7-COOHChEBI
N-Nonanoic acidChEBI
NonanoateChEBI
NonansaeureChEBI
Nonoic acidChEBI
Nonylic acidChEBI
Pelargic acidChEBI
PelargonChEBI
PelargonsaeureChEBI
Pergonic acidChEBI
1-NonanoateGenerator
1-OctanecarboxylateGenerator
N-NonanoateGenerator
Nonanoic acidGenerator
NonoateGenerator
NonylateGenerator
PelargateGenerator
PergonateGenerator
PelargonateGenerator
Cirrasol 185aHMDB
Emery 1202HMDB
Emery'S L-114HMDB
Emfac 1202HMDB
Hexacid C-9HMDB
N-NonoateHMDB
N-Nonoic acidHMDB
N-NonylateHMDB
N-Nonylic acidHMDB
N-PelargonateHMDB
N-Pelargonic acidHMDB
Pelargonic acid, calcium saltHMDB
Potassium nonanoateHMDB
Pelargonic acid, cadmium saltHMDB
Pelargonic acid, sodium saltHMDB
Pelargonic acid, zinc saltHMDB
Pelargonic acid, aluminum saltHMDB
Pelargonic acid, potassium saltHMDB
FA(9:0)HMDB
Pelargonic acidChEBI
Chemical FormulaC9H18O2
Average Molecular Weight158.238
Monoisotopic Molecular Weight158.13067982
IUPAC Namenonanoic acid
Traditional Namenonanoic acid
CAS Registry Number112-05-0
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 KeyFBUKVWPVBMHYJY-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point12.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 mg/mLNot Available
LogP3.42SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP3.47ALOGPS
logP3.14ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity44.88 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0910000000-29827f2f9240f991b625JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-2920000000-8730f6690cd20a58fcfcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9200000000-0842bd1d3fcea3f9f005JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08ml-9000000000-f9b45b786372be8b75d6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0930000000-30578d3edfa20cedf0e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-29827f2f9240f991b625JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2920000000-8730f6690cd20a58fcfcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-2e292fa3a6e414ce582aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-059f-9100000000-aaba2a9436e55f8d4c46JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06du-9200000000-bffc58a95ef321200ab9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0k9l-9400000000-fb4f24d4e9b0b4685763JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a3d26c56923a3cdddf9cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-a6e0c758ef2e822a5d73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-9200000000-0842bd1d3fcea3f9f005JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-08ml-9000000000-141c2435131c4b235390JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-0900000000-1efff6d47779ec04f434JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-c052a9b360e11f6a6eb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-1efff6d47779ec04f434JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c052a9b360e11f6a6eb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0900000000-b56762cc671f243abe6fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-2b95d53127d2c88c6b0cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-6900000000-e3f666b3dcf9b3b1c2feJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8432ab96716adadb8d13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-32f3915adea9c27b0b74JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1900000000-2ffdf4f1d36a54e86be1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-647e33e0c7198b77f78bJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-08ml-9000000000-e02b73fd7a397aa0b40bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Epidermis
  • Stratum Corneum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003306
KNApSAcK IDC00030829
Chemspider ID7866
KEGG Compound IDC01601
BioCyc IDCPD-8505
BiGG IDNot Available
Wikipedia LinkNonanoic_acid
METLIN ID5810
PubChem Compound8158
PDB IDNot Available
ChEBI ID29019
References
Synthesis ReferenceYu, 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
  1. Kuzmina N, Duval C, Johnsson S, Boman A, Lindberg M, Emtestam L: Assessment of irritant skin reactions using electrical impedance--a comparison between 2 laboratories. Contact Dermatitis. 2003 Jul;49(1):26-31. [PubMed:14641117 ]
  2. Willis CM, Stephens CJ, Wilkinson JD: Epidermal damage induced by irritants in man: a light and electron microscopic study. J Invest Dermatol. 1989 Nov;93(5):695-9. [PubMed:2794551 ]
  3. Anveden I, Lindberg M, Andersen KE, Bruze M, Isaksson M, Liden C, Sommerlund M, Wahlberg JE, Wilkinson JD, Willis CM: Oral prednisone suppresses allergic but not irritant patch test reactions in individuals hypersensitive to nickel. Contact Dermatitis. 2004 May;50(5):298-303. [PubMed:15209811 ]
  4. Wahlberg JE, Lindberg M: Nonanoic acid--an experimental irritant. Contact Dermatitis. 2003 Sep;49(3):117-23. [PubMed:14678207 ]
  5. Dowd PM, Kobza Black A, Woollard PM, Camp RD, Greaves MW: Cutaneous responses to 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE). J Invest Dermatol. 1985 Jun;84(6):537-41. [PubMed:3998504 ]
  6. Fullerton A, Rode B, Serup J: Skin irritation typing and grading based on laser Doppler perfusion imaging. Skin Res Technol. 2002 Feb;8(1):23-31. [PubMed:12005117 ]
  7. Agner T, Serup J: Individual and instrumental variations in irritant patch-test reactions--clinical evaluation and quantification by bioengineering methods. Clin Exp Dermatol. 1990 Jan;15(1):29-33. [PubMed:2311276 ]
  8. Matsuura E, Kobayashi K, Koike T, Shoenfeld Y: Autoantibody-mediated atherosclerosis. Autoimmun Rev. 2002 Dec;1(6):348-53. [PubMed:12848990 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM2A
Uniprot ID:
Q08AH3
Molecular weight:
64223.7
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:
ACSM2B
Uniprot ID:
Q68CK6
Molecular weight:
64270.78
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM3
Uniprot ID:
Q53FZ2
Molecular weight:
66152.235
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM5
Uniprot ID:
Q6NUN0
Molecular weight:
64759.55
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225