Showing Compound Card for Paullinic acid (CDB005265)

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Record Information
Version1.0
Created at2020-04-17 19:25:52 UTC
Updated at2020-12-07 19:11:51 UTC
CannabisDB IDCDB005265
Secondary Accession NumbersNot Available
Cannabis Compound 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. Paullinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Paullinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight310.51
Monoisotopic Molecular Weight310.2872
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.4ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPaullinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9550000000-a568fde49f01f4bff86fSpectrum
Predicted GC-MSPaullinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9651000000-0b21c94910de55c98564Spectrum
Predicted GC-MSPaullinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0006-0090000000-ab01f5fb032949f686ad2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-fac4c80d3081e8b3b5c52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-02vi-0193000000-5d9878771c6003135c312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03di-0149000000-fd505d52bb9e0d6e1b172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-03dl-1495000000-69de97a249f270595e462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-01r6-4892000000-646f945fc98f3bf346ba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-004m-5941000000-b492f3b08954e3a5529b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-05us-9600000000-d5ab265d673aac9b47b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0awa-9300000000-3f685ec5299d903413312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-05us-9200000000-f977085ed182d8a895a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0api-9100000000-dc195350c90d9d5444f22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-0api-9000000000-73db49cc4be80748474e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0190000000-710656f7efd37751d30a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0a4i-0490000000-050c4a7e6f32ea3755152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0900000000-d35906d7351e142a863e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0bvv-1920000000-d26dc4979fc630343cb72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-0390000000-8ad8df84242d4d8f960b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0006-1290000000-679d24cbb9090fd9f9ba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-7690000000-ba9ad589989cef510c642020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1097000000-38aaf259252ef8f750732016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-5491000000-60604ba44c7420adfc6b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-8950000000-73d56613f4cb3b60203d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-96e19787c146e6cffec72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2079000000-7b58a38dd8fd32b3b5ac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-757a0134c1c27398f2ca2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035159
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available