Paullinic acid

MUFA20:1Ω-7

  Overview

Stats

MUFA
Type
20
Carbons
1
Double bonds
0
Bis-allylic sites
310.5
Weight · g/mol
13.4 °C
Melting point
C20H38O2
Formula

Also known as

IUPAC (Z)-icos-13-enoic acid
Synonyms

  At a Glance

Key Points

An omega-7 fatty acid named after guaraná (Paullinia).

Source

Found in fish & seafood and plants.

Type

Long-chain monounsaturated fatty acid with 20 carbons and one cis double bond, an omega-7 fatty acid.

Identification

  Synonyms

Common Name Paullinic acid
IUPAC Name (Z)-icos-13-enoic acid
Traditional Name —
Other Synonyms
  • (Z)-eicos-13-enoic acid

  External IDs

General References
Wikipedia Paullinic_acid
Lipids
Lipid Maps LMFA01030367
Lipid Bank —
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB FDB013796
INFOODS —
Chemistry / Compounds
PubChem CID 5312518
CAS 17735-94-3
ChEBI 134479
ChEMBL —
ChemSpider 4471943
InChIKey —
ZINC ID ZINC000085663738
NIKKAJI ID J590.074C
PDBe —
UCI (UniChem) 32002755
SureChEMBL 2733334
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0035159
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1693
BioCyc/MetaCyc —
MetaNetX ID —
BiGG ID —
KEGG C21946
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD102020
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) CCL3CM45AT
FDA SRS (USA) CCL3CM45AT
NHPID (Canada) —
DTXSID (USA) DTXSID80402624
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-941-268
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 20:1 (4)

Other fatty acids sharing the 20:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Paullinic acid
(Z)-icos-13-enoic acid
 13Z —
5312518
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (3)
Gadoleic acid
(Z)-icos-9-enoic acid
 11Z —
5282767
Category —
Conjugation Type —
SMILES CCCCCCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Gondoic acid
(11Z)-icos-11-enoic acid
 9Z —
5282768
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Trans-gondoic acid
(E)-icos-11-enoic acid
 11E —
5282769
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Paullinic acid
Simple Notation 20:1
Notation 20:1(n-7)
IUPAC Name (Z)-icos-13-enoic acid
Structure:
Molecular C20H38O2
Structure CH3(CH2)5CH=CH(CH2)11COOH
SMILES CCCCCC\C=C/CCCCCCCCCCCC(=O)O
Cis / Trans cis
E-Z 13Z
Physical:
Weight 310.5 g/mol
Melting Point 13.4 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 9
ATP Yield (Net) 132.5 ATP