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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002327
Secondary Accession Numbers
  • HMDB02327
Metabolite Identification
Common Name1,11-Undecanedicarboxylic acid
Description1,11-Undecanedicarboxylic acid, also known as 1,13-tridecanedioic acid or brassilic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 1,11-Undecanedicarboxylic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752243
Synonyms
ValueSource
1,13-Tridecanedioic acidChEBI
Brassilic acidChEBI
Brassylic acidChEBI
Undecane-1,11-dicarboxylic acidChEBI
1,13-TridecanedioateGenerator
BrassilateGenerator
BrassylateGenerator
Undecane-1,11-dicarboxylateGenerator
1,11-UndecanedicarboxylateGenerator
TridecanedioateHMDB
Tridecanedioic acidHMDB, MeSH
Tridecanedioic acid, monosodium saltMeSH, HMDB
Tridecanedioic acid, disodium saltMeSH, HMDB
1,11-Undecanedicarboxylic acidChEBI
Chemical FormulaC13H24O4
Average Molecular Weight244.3273
Monoisotopic Molecular Weight244.167459256
IUPAC Nametridecanedioic acid
Traditional Namebrassylic acid
CAS Registry Number505-52-2
SMILES
OC(=O)CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C13H24O4/c14-12(15)10-8-6-4-2-1-3-5-7-9-11-13(16)17/h1-11H2,(H,14,15)(H,16,17)
InChI KeyDXNCZXXFRKPEPY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 mg/mL at 21 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.31ALOGPS
logP3.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity64.95 m³·mol⁻¹ChemAxon
Polarizability28.96 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]+161.01131661259
DarkChem[M-H]-157.16831661259
DeepCCS[M+H]+157.22530932474
DeepCCS[M-H]-153.20530932474
DeepCCS[M-2H]-190.84430932474
DeepCCS[M+Na]+166.50830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,11-Undecanedicarboxylic acidOC(=O)CCCCCCCCCCCC(O)=O3074.3Standard polar33892256
1,11-Undecanedicarboxylic acidOC(=O)CCCCCCCCCCCC(O)=O1874.4Standard non polar33892256
1,11-Undecanedicarboxylic acidOC(=O)CCCCCCCCCCCC(O)=O2056.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,11-Undecanedicarboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCC(=O)O2116.1Semi standard non polar33892256
1,11-Undecanedicarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCC(=O)O[Si](C)(C)C2207.9Semi standard non polar33892256
1,11-Undecanedicarboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCC(=O)O2372.8Semi standard non polar33892256
1,11-Undecanedicarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2721.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,11-Undecanedicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2900000000-ba32d0b598649fa5eb942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,11-Undecanedicarboxylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9781000000-c446656e5a369142c2732017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,11-Undecanedicarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0006-0090000000-38331eb24eac374bd3042012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0089-4980000000-e0f9e32666a9f5b5a8fa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0pb9-9030000000-92bad89a65219dbca8d72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 60V, Negative-QTOFsplash10-003r-0950000000-648f456d7f9ab1c4b2d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 45V, Negative-QTOFsplash10-003r-0890000000-bdc310014be796744f202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 15V, Negative-QTOFsplash10-0006-0090000000-17149e612e4f8c3b7d1d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 30V, Negative-QTOFsplash10-004l-0290000000-27e59d2b5c9e8c3a3c582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 75V, Negative-QTOFsplash10-003r-1930000000-3d4c069850987eb705a62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 60V, Positive-QTOFsplash10-003r-0950000000-ad8593ff000859ee8d392021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 10V, Positive-QTOFsplash10-004j-0190000000-0865b1cbfaacde80a7f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 20V, Positive-QTOFsplash10-002b-1950000000-c4a145d160c79293a2142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 40V, Positive-QTOFsplash10-0gyd-8900000000-36587d28463ba68e28152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 10V, Negative-QTOFsplash10-0006-0190000000-842c43a7d04e763b93e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 20V, Negative-QTOFsplash10-002f-0390000000-decb9669e3c353a66b632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 40V, Negative-QTOFsplash10-0a4l-9310000000-1a556ecc322f9074dc772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 10V, Positive-QTOFsplash10-004j-1690000000-bdbdb9d50f80993cb10a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 20V, Positive-QTOFsplash10-05s1-9420000000-8a8fd8287d51c96e45d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 40V, Positive-QTOFsplash10-0aor-9100000000-cf4f89db69167645b2c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 10V, Negative-QTOFsplash10-0006-0090000000-9627393074d8fc5d64782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 20V, Negative-QTOFsplash10-004i-1190000000-b5589ce36ff34845ec1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,11-Undecanedicarboxylic acid 40V, Negative-QTOFsplash10-0a6u-9820000000-45f94722fd7aa44d77cc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 IDFDB022963
KNApSAcK IDNot Available
Chemspider ID10026
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6622
PubChem Compound10458
PDB IDNot Available
ChEBI ID73718
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rocchiccioli F, Cartier PH, Aubourg P, Bougneres PF: Mass spectrometric identification of 2-hydroxy-sebacic acid in the urines of patients with neonatal adrenoleukodystrophy and Zellweger syndrome. Biomed Environ Mass Spectrom. 1986 Jun;13(6):315-8. [PubMed:2943344 ]