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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:30:56 UTC
HMDB IDHMDB0000772
Secondary Accession Numbers
  • HMDB00772
Metabolite Identification
Common NameNonadecanoic acid
DescriptionNonadecanoic acid, also known as n-nonadecanoic acid or nonadecylic acid or C19:0, 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, with nonadecanoic acid (its ester is called nonadecanoate) having 19 carbon atoms. Nonadecanoic acid is a very hydrophobic molecule, practically insoluble (in water). It is a solid with a melting point of 69.4°C. It can be found in bacteria, plants, and animals (including animal milk) (Nature 176:882; PMID: 14168161 ). It is secreted by termites (Rhinotermes marginalis) as part of its defence mechanism (Comp. Biochem. Physiol. B 71:731).
Structure
Data?1582752155
Synonyms
ValueSource
19:00ChEBI
C19:0ChEBI
N-Nonadecanoic acidChEBI
Nonadecylic acidChEBI
N-NonadecanoateGenerator
NonadecylateGenerator
NonadecanoateGenerator
N-NonadecylateHMDB
N-Nonadecylic acidHMDB
FA(19:0)HMDB
Nonadecanoic acidMeSH
Chemical FormulaC19H38O2
Average Molecular Weight298.5038
Monoisotopic Molecular Weight298.28718046
IUPAC Namenonadecanoic acid
Traditional Namenonadecanoic acid
CAS Registry Number646-30-0
SMILES
CCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21)
InChI KeyISYWECDDZWTKFF-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
  • 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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point69.4 °CNot Available
Boiling Point300.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.0019 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.339 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.8e-05 g/LALOGPS
logP10(8.42) g/LALOGPS
logP10(7.59) g/LChemAxon
logS10(-6.6) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity90.89 m³·mol⁻¹ChemAxon
Polarizability40.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.98631661259
DarkChem[M-H]-181.04331661259
AllCCS[M+H]+187.4432859911
AllCCS[M-H]-182.63832859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nonadecanoic acid,1TMS,#1CCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2340.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Nonadecanoic acid,1TBDMS,#1CCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2597.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nonadecanoic acid GC-MS (1 TMS)splash10-0159-2901000000-8299d54806ed60f141b22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nonadecanoic acid GC-MS (Non-derivatized)splash10-0159-2901000000-8299d54806ed60f141b22017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-5ddf2f951c9f519c81802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonadecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9560000000-957f37701ff9a82672f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0596-9100000000-66d168f75966d615344a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 10V, Positive-QTOFsplash10-000t-0090000000-6654f9a48cabdcfa7bd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 20V, Positive-QTOFsplash10-0uej-3590000000-ea8bf266e2e56c80950c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 40V, Positive-QTOFsplash10-052o-8930000000-74d1a96c59c53c06fed72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 10V, Negative-QTOFsplash10-0002-0090000000-d8acfab7a04e4b7e9a3a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 20V, Negative-QTOFsplash10-0f6t-1090000000-1e0b05eaf614093c806f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-5c078c32de5bf8b617862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 10V, Positive-QTOFsplash10-000t-2090000000-a0fd705e0619a1f47aa72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 20V, Positive-QTOFsplash10-053s-9370000000-c02fe769e6023d65c1c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-5fed4c847cf0c01c8bf72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 10V, Negative-QTOFsplash10-0002-0090000000-34ccf1c2200e0131ae8c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 20V, Negative-QTOFsplash10-002b-0090000000-4f9ff0b7c6bf7cd5b0f72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonadecanoic acid 40V, Negative-QTOFsplash10-0006-9130000000-0e59694e188057fbe82e2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year 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
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 QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
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 IDFDB004043
KNApSAcK IDC00053569
Chemspider ID12071
KEGG Compound IDC16535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNonadecylic_acid
METLIN ID5738
PubChem Compound12591
PDB IDNot Available
ChEBI ID39246
Food Biomarker OntologyNot Available
VMH IDM02613
MarkerDB IDNot Available
Good Scents IDrw1269641
References
Synthesis ReferenceLee, Donald G.; Lamb, Shannon E.; Chang, Victor S. Carboxylic acids from the oxidation of terminal alkenes by permanganate: nonadecanoic acid. Organic Syntheses (1981), 60 11-14.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ktsoyan ZA, Beloborodova NV, Sedrakyan AM, Osipov GA, Khachatryan ZA, Kelly D, Manukyan GP, Arakelova KA, Hovhannisyan AI, Olenin AY, Arakelyan AA, Ghazaryan KA, Aminov RI: Profiles of Microbial Fatty Acids in the Human Metabolome are Disease-Specific. Front Microbiol. 2011 Jan 20;1:148. doi: 10.3389/fmicb.2010.00148. eCollection 2010. [PubMed:21687748 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  3. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]