NP-MRD: Showing NP-Card for 12-KETE (NP0339374)

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Record Information

Version

2.0

Created at

2024-09-11 21:31:09 UTC

Updated at

2024-09-11 21:31:10 UTC

NP-MRD ID

NP0339374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-KETE

Description

12-KETE, also known as 12-keto-ete or 12-oxoete, 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. Thus, 12-KETE is considered to be an eicosanoid lipid molecule. 12-KETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 12-KETE was first documented in 1989 (PMID: 2774398). In humans, 12-KETE is involved in mefenamic acid action pathway.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271200282D          

 23 22  0  0  0  0            999 V2000
   18.6048   -6.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1923   -7.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3673   -7.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9548   -8.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1298   -8.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7173   -9.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8923   -9.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797   -8.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6547   -8.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2422   -7.6784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2422   -9.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6547   -9.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2422  -10.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6547  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8923  -11.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7173  -11.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1298  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9548  -11.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3673  -10.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1923  -10.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6048  -11.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6048   -9.8218    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  1  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  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339374

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+

> <INCHI_KEY>
GURBRQGDZZKITB-VXBMJZGYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.42068476428278

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
5.767698232000001

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.57826867951469

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.88963050730466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.681356978761349

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
100.57209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-oxo-ETE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      34.729 -12.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.959 -14.333   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.419 -14.333   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.649 -15.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.109 -15.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.339 -17.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.799 -17.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.029 -15.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.489 -15.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.719 -14.333   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.719 -17.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.489 -18.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.719 -19.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.489 -21.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.029 -21.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.799 -22.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.339 -22.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.109 -21.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.649 -21.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.419 -19.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.959 -19.668   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      34.729 -21.001   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      34.729 -18.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   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   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
(5Z,8Z,10E,14Z)-12-Oxoeicosa-5,8,10,14-tetraenoic acid	ChEBI
(5Z,8Z,10E,14Z)-12-Oxoicosa-5,8,10,14-tetraenoic acid	ChEBI
12-Keto-ete	ChEBI
12-Ketoeicosatetraenoic acid	ChEBI
12-oxo, 5C,8C,10t,14C-20:4	ChEBI
12-OxoETE	ChEBI
(5Z,8Z,10E,14Z)-12-Oxoeicosa-5,8,10,14-tetraenoate	Generator
(5Z,8Z,10E,14Z)-12-Oxoicosa-5,8,10,14-tetraenoate	Generator
12-Ketoeicosatetraenoate	Generator
12-oxo-ETE	HMDB
12-Keto-5,8,11,13-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(5Z,8Z,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid

Traditional Name

12-oxo-ETE

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/CC(=O)\C=C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+

InChI Key

GURBRQGDZZKITB-VXBMJZGYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

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
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
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

oxoicosatetraenoic acid (CHEBI:34151 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14807 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060019 )

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	5.79	ALOGPS
logP	5.77	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	100.57 m³·mol⁻¹	ChemAxon
Polarizability	37.42 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

HMDB0013633

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029609

KNApSAcK ID

Not Available

Chemspider ID

4446286

KEGG Compound ID

C14807

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283162

PDB ID

Not Available

ChEBI ID

34151

Good Scents ID

Not Available

References

General References

Piomelli D, Feinmark SJ, Shapiro E, Schwartz JH: 12-keto-eicosatetraenoic acid. A biologically active eicosanoid in the nervous system of Aplysia. Ann N Y Acad Sci. 1989;559:208-18. doi: 10.1111/j.1749-6632.1989.tb22610.x. [PubMed:2774398 ]

Showing NP-Card for 12-KETE (NP0339374)

MOL for NP0339374 (12-KETE)

3D MOL for NP0339374 (12-KETE)

3D SDF for NP0339374 (12-KETE)

3D-SDF for NP0339374 (12-KETE)

PDB for NP0339374 (12-KETE)

3D PDB for NP0339374 (12-KETE)

SMILES for NP0339374 (12-KETE)

INCHI for NP0339374 (12-KETE)

Structure for NP0339374 (12-KETE)

3D Structure for NP0339374 (12-KETE)