NP-MRD: Showing NP-Card for 5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid (NP0050339)

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Record Information

Version

2.0

Created at

2022-04-27 20:53:56 UTC

Updated at

2022-04-27 20:53:56 UTC

NP-MRD ID

NP0050339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid

Description

(5Z,7E,9E,14Z,17Z)-icosapentaenoic acid, also known as (5Z,7E,9E,14Z,17Z)-eicosapentaenoate, 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. 5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid is found in Ptilota filicina. Based on a literature review very few articles have been published on (5Z,7E,9E,14Z,17Z)-icosapentaenoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222532D          

 22 21  0  0  0  0            999 V2000
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -7.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -7.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/CCC\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/h3-4,6-7,11-16H,2,5,8-10,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,12-11+,14-13+,16-15-

> <INCHI_KEY>
XGTCGDUVXWLURC-FZNBEQTOSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.7995041783502

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,7E,9E,14Z,17Z)-icosa-5,7,9,14,17-pentaenoic acid

> <ALOGPS_LOGP>
6.61

> <JCHEM_LOGP>
6.225249154333334

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.856996919353176

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
101.0706

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,7E,9E,14Z,17Z)-icosa-5,7,9,14,17-pentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   0.976   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.357   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.691  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691  -3.644   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.025  -4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.025  -5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.358  -6.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.358  -8.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.692  -9.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.692 -10.574   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.358 -11.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.358 -12.884   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.025 -13.654   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.691 -12.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.357 -13.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.977   0.206   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.311  -2.104   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(5Z,7E,9E,14Z,17Z)-Eicosapentaenoate	ChEBI
(5Z,7E,9E,14Z,17Z)-Eicosapentaenoic acid	ChEBI
5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid	Kegg
(5Z,7E,9E,14Z,17Z)-Icosa-5,7,9,14,17-pentaenoic acid	Kegg
5Z,7E,9E,14Z,17Z-Eicosapentaenoate	Generator
(5Z,7E,9E,14Z,17Z)-Icosa-5,7,9,14,17-pentaenoate	Generator
(5Z,7E,9E,14Z,17Z)-Icosapentaenoate	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(5Z,7E,9E,14Z,17Z)-icosa-5,7,9,14,17-pentaenoic acid

Traditional Name

(5Z,7E,9E,14Z,17Z)-icosa-5,7,9,14,17-pentaenoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/CCC\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/h3-4,6-7,11-16H,2,5,8-10,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,12-11+,14-13+,16-15-

InChI Key

XGTCGDUVXWLURC-FZNBEQTOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ptilota filicina	-	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-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 Framework

Aliphatic acyclic compounds

External Descriptors

icosapentaenoic acid (CHEBI:29457 )
Polyunsaturated fatty acids (C12083 )
Unsaturated fatty acids (LMFA01030760 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.61	ALOGPS
logP	6.23	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	101.07 m³·mol⁻¹	ChemAxon
Polarizability	37.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000438

Chemspider ID

4445288

KEGG Compound ID

C12083

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282061

PDB ID

Not Available

ChEBI ID

29457

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid (NP0050339)

MOL for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

3D MOL for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

3D SDF for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

3D-SDF for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

PDB for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

3D PDB for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

SMILES for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

INCHI for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

Structure for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)

3D Structure for NP0050339 (5Z,7E,9E,14Z,17Z-Eicosapentaenoic acid)