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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:21:31 UTC
HMDB IDHMDB0000947
Secondary Accession Numbers
  • HMDB00947
Metabolite Identification
Common NameUndecanoic acid
DescriptionUndecanoic acid is a medium chain length monocarboxylic acid that appears to be involved in the control of triacylglycerol synthesis.(PMID 1739406 ). It is found in breast milk produced by women in the United States (PMID 16332663 ), in infant formulas ( Mljekarstvo (2005), 55(2), 101-112.), in seminal plasma (PMID 736283 ), and other fluids (PMID 8548929 ).
Structure
Thumb
Synonyms
ValueSource
1-Decanecarboxylic acidChEBI
CH3-[CH2]9-COOHChEBI
Hendecanoic acidChEBI
N-Undecanoic acidChEBI
N-Undecoic acidChEBI
N-Undecylic acidChEBI
UDAChEBI
Undecoic acidChEBI
Undecylic acidChEBI
UndekansaeureChEBI
1-DecanecarboxylateGenerator
UndecanoateGenerator
HendecanoateGenerator
N-UndecanoateGenerator
N-UndecoateGenerator
N-UndecylateGenerator
UndecoateGenerator
UndecylateGenerator
Chemical FormulaC11H22O2
Average Molecular Weight186.2912
Monoisotopic Molecular Weight186.161979948
IUPAC Nameundecanoic acid
Traditional Nameundecanoic acid
CAS Registry Number112-37-8
SMILES
CCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChI KeyZDPHROOEEOARMN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 mg/mLNot Available
LogP4.42SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.49ALOGPS
logP4.03ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity54.08 m³·mol⁻¹ChemAxon
Polarizability23.73 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-MS (1 TMS)splash10-0159-2910000000-722a87fa01fa27b58b07View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0706-9000000000-d7f6a00a2bcfd58539f5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2910000000-722a87fa01fa27b58b07View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9400000000-c452aa611294afd4b227View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9310000000-90668bb3fcf413ecc767View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-4e46062530f2b87127f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-2900000000-1bd11599567676fd18b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0019-3900000000-3ed16e9aae084b8128f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0706-9000000000-f0f2855ce0a7d3e0e44cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-70bc980554bccc2d565fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-1923c2ee9004b1a4f217View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-818107787c04dbc613beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-01t9-9000000000-da3c8186be5724d14262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052f-9000000000-4a1e2f342d24eb6ec79eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0090000000-2dadd8baad50427686a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03di-0090000000-2dadd8baad50427686a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-d09512035285f332d56cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-fca225c5971e85f0f121View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0900000000-0fabd46bd1eaa73e5af0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-d09512035285f332d56cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-70bc980554bccc2d565fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1923c2ee9004b1a4f217View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-f871962b32a5d16913f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01t9-9000000000-f75b1abf45a6ce1d1e16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-5e1b204d52a76537f6ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-4900000000-4156178f661bac3b8785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8f8e8441132607db272aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-36794ad067903d2b6624View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-157dc43c0ad4ff0f5509View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-95af6ebcd3a0e83715bdView in MoNA
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-e152e90785434b58612cView 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 (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000700
KNApSAcK IDC00007421
Chemspider ID7888
KEGG Compound IDC17715
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5894
PubChem Compound8180
PDB ID11A
ChEBI ID32368
References
Synthesis ReferenceSchreyer, Gerd; Schwarze, Werner; Weigert, Wolfgang. Carboxylic acids by oxidation of vicinal diols. Ger. Offen. (1972), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Avrahami D, Shai Y: Conjugation of a magainin analogue with lipophilic acids controls hydrophobicity, solution assembly, and cell selectivity. Biochemistry. 2002 Feb 19;41(7):2254-63. [PubMed:11841217 ]
  2. Avrahami D, Shai Y: Bestowing antifungal and antibacterial activities by lipophilic acid conjugation to D,L-amino acid-containing antimicrobial peptides: a plausible mode of action. Biochemistry. 2003 Dec 23;42(50):14946-56. [PubMed:14674771 ]
  3. Mingrone G, Greco AV, Capristo E, Benedetti G, Castagneto M, Gasbarrini G: An improved GLC method for a rapid, simultaneous analysis of both medium chain fatty acids and medium chain triglycerides in plasma. Clin Chim Acta. 1995 Sep 15;240(2):195-207. [PubMed:8548929 ]
  4. Kinkaid AR, Wilton DC: A continuous fluorescence displacement assay for phospholipase A2 using albumin and medium chain phospholipid substrates. Anal Biochem. 1993 Jul;212(1):65-70. [PubMed:8368517 ]
  5. Hamfler HW, Nissen HP, Heinze I, Kreysel HW, Schirren C: [Free fatty acid composition of human semen in different clinical diagnoses]. Andrologia. 1978 Nov-Dec;10(6):498-50. [PubMed:736283 ]
  6. Mosley EE, Wright AL, McGuire MK, McGuire MA: trans Fatty acids in milk produced by women in the United States. Am J Clin Nutr. 2005 Dec;82(6):1292-7. [PubMed:16332663 ]
  7. Hornung B, Amtmann E, Sauer G: Medium chain length fatty acids stimulate triacylglycerol synthesis in tissue culture cells. Biochem Pharmacol. 1992 Jan 22;43(2):175-81. [PubMed:1739406 ]
  8. Dutta-Roy AK, Demarco AC, Raha SK, Shay J, Garvey M, Horrobin DF: Effects of linoleic and gamma-linolenic acids (efamol evening primrose oil) on fatty acid-binding proteins of rat liver. Mol Cell Biochem. 1990 Oct 15-Nov 8;98(1-2):177-82. [PubMed:2176271 ]
  9. (). Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990. .

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