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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 20:06:20 UTC
Update Date2019-07-23 06:17:55 UTC
HMDB IDHMDB0035159
Secondary Accession Numbers
  • HMDB35159
Metabolite Identification
Common NamePaullinic acid
DescriptionPaullinic acid, also known as C20:1N-7 or (Z)-13-icosenoate, 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. Based on a literature review a significant number of articles have been published on Paullinic acid.
Structure
Data?1563862675
Synonyms
ValueSource
(13Z)-Eicos-13-enoic acidChEBI
(Z)-13-Eicosenoic acidChEBI
(Z)-13-Icosenoic acidChEBI
(Z)-Eicos-13-enoic acidChEBI
13Z-Eicosenoic acidChEBI
C20:1N-7ChEBI
cis-13-Eicosenoic acidChEBI
(13Z)-Eicos-13-enoateGenerator
(Z)-13-EicosenoateGenerator
(Z)-13-IcosenoateGenerator
(Z)-Eicos-13-enoateGenerator
13Z-EicosenoateGenerator
cis-13-EicosenoateGenerator
PaullinateGenerator
Chemical FormulaC20H38O2
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
IUPAC Name(13Z)-icos-13-enoic acid
Traditional Namepaullinic acid
CAS Registry Number17735-94-3
SMILES
CCCCCC\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h7-8H,2-6,9-19H2,1H3,(H,21,22)/b8-7-
InChI KeyURXZXNYJPAJJOQ-FPLPWBNLSA-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
  • Unsaturated 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
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point13.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.0e-05 g/LALOGPS
logP10(8.4) g/LALOGPS
logP10(7.67) g/LChemAxon
logS10(-6.8) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m³·mol⁻¹ChemAxon
Polarizability41.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.731661259
DarkChem[M-H]-185.41631661259
DeepCCS[M+H]+182.80330932474
DeepCCS[M-H]-178.78330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Paullinic acidCCCCCC\C=C/CCCCCCCCCCCC(O)=O3360.2Standard polar33892256
Paullinic acidCCCCCC\C=C/CCCCCCCCCCCC(O)=O2285.7Standard non polar33892256
Paullinic acidCCCCCC\C=C/CCCCCCCCCCCC(O)=O2349.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Paullinic acid,1TMS,isomer #1CCCCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C2417.5Semi standard non polar33892256
Paullinic acid,1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2687.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Paullinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9550000000-a568fde49f01f4bff86f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Paullinic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9651000000-0b21c94910de55c985642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Paullinic 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 - Paullinic acid n/a 21V, negative-QTOFsplash10-0006-0090000000-ab01f5fb032949f686ad2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-0006-0290000000-fac4c80d3081e8b3b5c52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-02vi-0193000000-5d9878771c6003135c312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 3V, positive-QTOFsplash10-03di-0149000000-fd505d52bb9e0d6e1b172020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 5V, positive-QTOFsplash10-03dl-1495000000-69de97a249f270595e462020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 7V, positive-QTOFsplash10-01r6-4892000000-646f945fc98f3bf346ba2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 9V, positive-QTOFsplash10-004m-5941000000-b492f3b08954e3a5529b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 13V, positive-QTOFsplash10-05us-9600000000-d5ab265d673aac9b47b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 17V, positive-QTOFsplash10-0awa-9300000000-3f685ec5299d903413312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 19V, positive-QTOFsplash10-05us-9200000000-f977085ed182d8a895a22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 22V, positive-QTOFsplash10-0api-9100000000-dc195350c90d9d5444f22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 28V, positive-QTOFsplash10-0api-9000000000-73db49cc4be80748474e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-0006-0190000000-710656f7efd37751d30a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-0a4i-0490000000-050c4a7e6f32ea3755152020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-0006-0900000000-d35906d7351e142a863e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-0bvv-1920000000-d26dc4979fc630343cb72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid n/a 21V, positive-QTOFsplash10-004i-0390000000-8ad8df84242d4d8f960b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 8V, positive-QTOFsplash10-0006-1290000000-679d24cbb9090fd9f9ba2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Paullinic acid Orbitrap 10V, positive-QTOFsplash10-0006-7690000000-ba9ad589989cef510c642020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 10V, Positive-QTOFsplash10-03dl-1097000000-38aaf259252ef8f750732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 20V, Positive-QTOFsplash10-0gb9-5491000000-60604ba44c7420adfc6b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 40V, Positive-QTOFsplash10-0f6x-8950000000-73d56613f4cb3b60203d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 10V, Negative-QTOFsplash10-0a4i-0029000000-96e19787c146e6cffec72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 20V, Negative-QTOFsplash10-0a4i-2079000000-7b58a38dd8fd32b3b5ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Paullinic acid 40V, Negative-QTOFsplash10-0a4l-9140000000-757a0134c1c27398f2ca2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.722 +/- 5.378 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013796
KNApSAcK IDNot Available
Chemspider ID4471943
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPaullinic_acid
METLIN IDNot Available
PubChem Compound5312518
PDB IDNot Available
ChEBI ID134479
Food Biomarker OntologyNot Available
VMH IDM00017
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.