Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 17:43:45 UTC
HMDB IDHMDB0000888
Secondary Accession Numbers
  • HMDB00888
Metabolite Identification
Common NameUndecanedioic acid
DescriptionUndecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID:131675 ). Undecanedioic acid has been found (among other unusual dicarboxylic acids) in the urine from patients under hopantenate therapy during episodes of Reye's-like syndrome. (PMID:2331533 ).
Structure
Data?1582752162
Synonyms
ValueSource
1,11-Undecanedioic acidChEBI
1,9-Nonanedicarboxylic acidChEBI
Hendecanedioic acidChEBI
Undecanedionic acidChEBI
1,11-UndecanedioateGenerator
1,9-NonanedicarboxylateGenerator
HendecanedioateGenerator
UndecanedionateGenerator
UndecanedioateGenerator
Chemical FormulaC11H20O4
Average Molecular Weight216.2741
Monoisotopic Molecular Weight216.136159128
IUPAC Nameundecanedioic acid
Traditional Nameundecanedioic acid
CAS Registry Number1852-04-6
SMILES
OC(=O)CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)
InChI KeyLWBHHRRTOZQPDM-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
  • Dicarboxylic 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 effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point108 - 110 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.1 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP2.41ALOGPS
logP2.71ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity55.74 m³·mol⁻¹ChemAxon
Polarizability24.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.60431661259
DarkChem[M-H]-149.57531661259
AllCCS[M+H]+150.53232859911
AllCCS[M-H]-153.09232859911
DeepCCS[M+H]+149.81130932474
DeepCCS[M-H]-145.87330932474
DeepCCS[M-2H]-183.16930932474
DeepCCS[M+Na]+158.85130932474
AllCCS[M+H]+150.532859911
AllCCS[M+H-H2O]+147.032859911
AllCCS[M+NH4]+153.832859911
AllCCS[M+Na]+154.732859911
AllCCS[M-H]-153.132859911
AllCCS[M+Na-2H]-154.132859911
AllCCS[M+HCOO]-155.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Undecanedioic acidOC(=O)CCCCCCCCCC(O)=O2813.4Standard polar33892256
Undecanedioic acidOC(=O)CCCCCCCCCC(O)=O1682.9Standard non polar33892256
Undecanedioic acidOC(=O)CCCCCCCCCC(O)=O1867.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Undecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O1908.4Semi standard non polar33892256
Undecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O[Si](C)(C)C2008.9Semi standard non polar33892256
Undecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O2160.3Semi standard non polar33892256
Undecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2499.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-db85d280b172836331b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9770000000-a2d73ceb282e8a18157e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-014i-0290000000-7ae807700c28584d2e282012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0f6t-2900000000-3f0c97ba1c386d6554642012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0fr2-9230000000-6e48936ad64fc2b1149b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 90V, Positive-QTOFsplash10-0pc0-9400000000-6a74432b9f7f562198432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 75V, Positive-QTOFsplash10-0udi-3900000000-e126e8f774ea9180ce4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 75V, Negative-QTOFsplash10-0udi-3900000000-cb662d0a491d854337842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 90V, Negative-QTOFsplash10-0pc0-9400000000-001aea13ac806299ab1f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 45V, Negative-QTOFsplash10-0udj-0910000000-9adbb3ad23909d9d4e782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 60V, Negative-QTOFsplash10-0udi-0910000000-1d421e549e1033a05df12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 30V, Negative-QTOFsplash10-0fr2-0940000000-35fc1c6ae29a4b119c972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanedioic acid 15V, Negative-QTOFsplash10-014j-0690000000-83bc5df70a0bb38f91352021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Positive-QTOFsplash10-00kb-0930000000-92c504d7493b685337092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Positive-QTOFsplash10-00r2-1910000000-84e296521dd0030ce1642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Positive-QTOFsplash10-01td-9500000000-a014eaf3810192591c952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Negative-QTOFsplash10-014i-0390000000-8d3496492a9c0c8977b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Negative-QTOFsplash10-014j-1970000000-690951ba65eb6d7209ee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9400000000-c06fbfff105dafce26352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Positive-QTOFsplash10-00kb-1920000000-1af20d2caa8369d83f792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Positive-QTOFsplash10-0aps-9300000000-1eeafdbc57daff9241522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Positive-QTOFsplash10-0a4l-9100000000-0a7400e1d784601b32e52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 10V, Negative-QTOFsplash10-014i-0390000000-9163a48488a98a354cde2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 20V, Negative-QTOFsplash10-0002-1920000000-ee6e1dd82e64cf1046a32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanedioic acid 40V, Negative-QTOFsplash10-054p-8900000000-7c2f170d31d14a2e1a372021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.44(0.28-0.54) uMInfant (0-1 year old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.79-4.8 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIron deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
3-Hydroxydicarboxylic aciduria
  1. Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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
FooDB IDFDB022300
KNApSAcK IDNot Available
Chemspider ID15037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5846
PubChem Compound15816
PDB IDNot Available
ChEBI ID73713
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1296061
References
Synthesis ReferenceDurham, Lois J.; McLeod, Donald J.; Cason, James. Hendecanedioic acid. Organic Syntheses (1958), 38 34-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Claire M, Jacotot B, Robert L: Characterization of lipids associated with macromolecules of the intercellular matrix of human aorta. Connect Tissue Res. 1976;4(2):61-71. [PubMed:131675 ]
  2. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I, Kajita M: Mass spectrometric identification of 2-hydroxydodecanedioic acid and its homologues in urine from patients with hopantenate therapy during clinical episode. Biomed Environ Mass Spectrom. 1990 Mar;19(3):171-5. [PubMed:2331533 ]