Np mrd loader

Showing NP-Card for (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate (NP0334559)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-10 18:54:01 UTC
Updated at2024-09-10 18:54:01 UTC
NP-MRD IDNP0334559
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate
DescriptionEicosapentaenoic acid, also known as icosapent or cis-5,8,11,14,17-epa, 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. Eicosapentaenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, eicosapentaenoic acid participates in a number of enzymatic reactions. In particular, eicosapentaenoic acid can be biosynthesized from cis-8,11,14,17-eicosatetraenoic acid through its interaction with the enzyme fatty acid desaturase 1. In addition, eicosapentaenoic acid can be converted into docosapentaenoic acid (22N-3); which is catalyzed by the enzyme elongation OF very long chain fatty acids protein 5. In humans, eicosapentaenoic acid is involved in alpha linolenic acid and linoleic acid metabolism. Outside of the human body, Eicosapentaenoic acid has been detected, but not quantified in, several different foods, such as common hazelnuts, rowanberries, irish moss, wax apples, and tamarinds. This could make eicosapentaenoic acid a potential biomarker for the consumption of these foods. Eicosapentaenoic acid, with regard to humans, has been found to be associated with several diseases such as hypertension, essential hypertension, colorectal cancer, and major depressive disorder; eicosapentaenoic acid has also been linked to the inborn metabolic disorder isovaleric acidemia. It was first documented in 1996 (PMID: 8635279). An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17 (PMID: 8704924) (PMID: 15930517) (PMID: 12384078) (PMID: 16872308).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

 
  Mrv0541 05281313312D          
 
 22 21  0  0  0  0            999 V2000
   12.8416  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6781  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0886  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3892  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3775  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1003  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5409  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9369  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8299  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6898  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0769  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4009  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3658  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2375  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9486  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9018  -11.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7015  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5381  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2492  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9603  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
Download

3D MOL for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)

Download
3D SDF for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
 
  Mrv0541 05281313312D          
 
 22 21  0  0  0  0            999 V2000
   12.8416  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6781  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0886  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3892  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3775  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1003  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5409  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9369  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8299  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6898  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0769  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4009  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3658  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2375  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9486  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9018  -11.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -10.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7015  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5381  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2492  -11.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9603  -10.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
JAZBEHYOTPTENJ-JLNKQSITSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.92931841565799

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

> <ALOGPS_LOGP>
6.53

> <JCHEM_LOGP>
6.225249154333334

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
101.07059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eicosapentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
Download
PDB for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
HEADER    PROTEIN                                 28-MAY-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-13         0                                  
HETATM    1  C   UNK     0      23.971 -20.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.532 -20.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.565 -21.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.860 -21.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.238 -20.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.187 -20.379   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.676 -20.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.749 -20.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.349 -21.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.154 -21.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.944 -20.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.482 -20.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.616 -21.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.043 -20.379   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.289 -20.379   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.371 -21.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.883 -21.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      14.289 -18.817   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.776 -20.379   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.338 -20.379   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.665 -21.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      40.993 -20.379   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

Download
3D PDB for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
Download
SMILES for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Download
INCHI for NP0334559 ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate)
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
Download
View in JSmol
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACIDChEBI
5,8,11,14,17-Icosapentaenoic acidChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acidChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acidChEBI
cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
cis-5,8,11,14,17-EPAChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acidChEBI
EPAChEBI
IcosapentChEBI
Icosapentaenoic acidChEBI
IcosapentoChEBI
IcosapentumChEBI
Timnodonic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-IcosapentaenoateKegg
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EicosapentaenoateGenerator
(all-Z)-5,8,11,14,17-EicosapentaenoateGenerator
5,8,11,14,17-EICOSAPENTAENOateGenerator
5,8,11,14,17-IcosapentaenoateGenerator
all-cis-5,8,11,14,17-EicosapentaenoateGenerator
all-cis-Icosa-5,8,11,14,17-pentaenoateGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoateGenerator
cis-5,8,11,14,17-EicosapentaenoateGenerator
cis-delta(5,8,11,14,17)-EicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoic acidGenerator
IcosapentaenoateGenerator
TimnodonateGenerator
5Z,8Z,11Z,14Z,17Z-EicosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoateGenerator
EicosapentaenoateGenerator
Omega-3-eicosapentaenoic acidHMDB
Acid, eicosapentanoicHMDB
Eicosapentanoic acidHMDB
Omega 3 eicosapentaenoic acidHMDB
all-cis-IcosapentaenoateHMDB
all-cis-Icosapentaenoic acidHMDB
(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acidHMDB
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acidHMDB
(all-Z)-Δ5,8,11,14,17-eicosapentaenoic acidHMDB
(all-cis)-5,8,11,14,17-Eicosapentaenoic acidHMDB
FA(20:5(5Z,8Z,11Z,14Z,17Z))HMDB
FA(20:5n3)HMDB
Eicosapentaenoic acidHMDB
Chemical FormulaC20H30O2
Average Mass302.4510 Da
Monoisotopic Mass302.22458 Da
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Nameeicosapentaenoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyJAZBEHYOTPTENJ-JLNKQSITSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m³·mol⁻¹ChemAxon
Polarizability35.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001999  
DrugBank IDDB00159  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030126  
KNApSAcK IDC00001215  
Chemspider ID393682  
KEGG Compound IDC06428  
BioCyc IDEICOSAPENTAENOATE  
BiGG ID2218016  
Wikipedia LinkEicosapentaenoic acid  
METLIN ID6423  
PubChem Compound446284  
PDB IDNot Available
ChEBI ID28364  
Good Scents IDNot Available
References
General References
  1. Sipka S, Dey I, Buda C, Csongor J, Szegedi G, Farkas T: The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes. Clin Immunol Immunopathol. 1996 Jun;79(3):224-8. doi: 10.1006/clin.1996.0072. [PubMed:8635279  ] 
  2. Miwa H, Yamamoto M, Futata T, Kan K, Asano T: Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration. J Chromatogr B Biomed Appl. 1996 Mar 3;677(2):217-23. doi:  10.1016/0378-4347(95)00445-9. [PubMed:8704924  ] 
  3. Kim HH, Shin CM, Park CH, Kim KH, Cho KH, Eun HC, Chung JH: Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts. J Lipid Res. 2005 Aug;46(8):1712-20. doi: 10.1194/jlr.M500105-JLR200. Epub 2005  Jun 1. [PubMed:15930517  ] 
  4. Gillis RC, Daley BJ, Enderson BL, Karlstad MD: Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells. J Surg Res. 2002 Sep;107(1):145-53. doi: 10.1006/jsre.2002.6496. [PubMed:12384078  ] 
  5. Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. [PubMed:16872308  ]