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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:50:20 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
Thumb
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
PelargonateGenerator
1-OctanecarboxylateGenerator
N-NonanoateGenerator
Nonanoic acidGenerator
NonoateGenerator
NonylateGenerator
PelargateGenerator
PergonateGenerator
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 saltMeSH
Potassium nonanoateMeSH
Pelargonic acid, cadmium saltMeSH
Pelargonic acid, sodium saltMeSH
Pelargonic acid, zinc saltMeSH
Pelargonic acid, aluminum saltMeSH
Pelargonic acid, potassium saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Indirect biological 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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0910000000-29827f2f9240f991b625View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-2920000000-8730f6690cd20a58fcfcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9200000000-0842bd1d3fcea3f9f005View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08ml-9000000000-f9b45b786372be8b75d6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0930000000-30578d3edfa20cedf0e8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-29827f2f9240f991b625View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2920000000-8730f6690cd20a58fcfcView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-2e292fa3a6e414ce582aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-059f-9100000000-aaba2a9436e55f8d4c46View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06du-9200000000-bffc58a95ef321200ab9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0k9l-9400000000-fb4f24d4e9b0b4685763View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a3d26c56923a3cdddf9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-a6e0c758ef2e822a5d73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-9200000000-0842bd1d3fcea3f9f005View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-08ml-9000000000-141c2435131c4b235390View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-0900000000-1efff6d47779ec04f434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-c052a9b360e11f6a6eb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-1efff6d47779ec04f434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c052a9b360e11f6a6eb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0900000000-b56762cc671f243abe6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-2b95d53127d2c88c6b0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-6900000000-e3f666b3dcf9b3b1c2feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8432ab96716adadb8d13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-32f3915adea9c27b0b74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1900000000-2ffdf4f1d36a54e86be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-647e33e0c7198b77f78bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-08ml-9000000000-e02b73fd7a397aa0b40bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
Tissue Location
  • Epidermis
  • Stratum Corneum
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
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
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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003306
KNApSAcK IDC00030829
Chemspider ID7866
KEGG Compound IDC01601
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPelargonic acid
METLIN ID5810
PubChem Compound8158
PDB IDKNA
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