NP-MRD: Showing NP-Card for 20-Oxo-leukotriene E4 (NP0339081)

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Record Information

Version

2.0

Created at

2024-09-11 19:35:55 UTC

Updated at

2024-09-11 19:35:55 UTC

NP-MRD ID

NP0339081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-Oxo-leukotriene E4

Description

20-Oxo-leukotriene E4, also known as 20-oxo-lte(,4), belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative. Thus, 20-oxo-leukotriene E4 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 20-Oxo-leukotriene E4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. All mammalian cells except erythrocytes synthesize eicosanoids. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Leukotriene E4 (LTE4) is a cysteinyl leukotriene.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 31 30  0  0  1  0            999 V2000
    8.6523  -14.1584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6523  -13.3334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3667  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0812  -13.3334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957  -12.9209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5102  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -12.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7970  -11.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7970  -10.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826   -9.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681   -9.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681   -8.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536   -7.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536   -7.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957  -12.0958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0812  -11.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102  -11.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102  -10.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246   -9.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102   -9.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391   -9.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377  -12.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2233  -13.3334    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
  2 29  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  1  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  2  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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END


  Mrv0541 02251208092D          

 31 30  0  0  1  0            999 V2000
    8.6523  -14.1584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6523  -13.3334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3667  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0812  -13.3334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957  -12.9209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5102  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681  -13.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -12.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7970  -11.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7970  -10.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0826   -9.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681   -9.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681   -8.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536   -7.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536   -7.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7957  -12.0958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0812  -11.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102  -11.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102  -10.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246  -10.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246   -9.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5102   -9.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391   -9.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377  -12.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2233  -13.3334    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
  2 29  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  1  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  2  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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC=O)[C@@H](O)CCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO6S/c24-19(23(29)30)18-31-21(20(26)14-13-16-22(27)28)15-11-9-7-5-3-1-2-4-6-8-10-12-17-25/h2-5,7,9,11,15,17,19-21,26H,1,6,8,10,12-14,16,18,24H2,(H,27,28)(H,29,30)/b4-2-,5-3-,9-7+,15-11+/t19-,20+,21-/m1/s1

> <INCHI_KEY>
DXFWBOQUFGDWDP-HEZGWBLQSA-N

> <FORMULA>
C23H35NO6S

> <MOLECULAR_WEIGHT>
453.592

> <EXACT_MASS>
453.218508547

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
50.80220248489687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.5422213354620429

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.456034189181412

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3851298537664922

> <JCHEM_PKA_STRONGEST_BASIC>
9.130042752836843

> <JCHEM_POLAR_SURFACE_AREA>
137.92000000000002

> <JCHEM_REFRACTIVITY>
128.35969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  N   UNK     0      16.151 -26.429   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      16.151 -24.889   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.485 -24.119   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      18.818 -24.889   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      20.152 -24.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.486 -24.889   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.819 -24.119   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.153 -24.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.487 -24.119   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.820 -24.889   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.154 -24.119   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.154 -22.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.488 -21.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.488 -20.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.154 -19.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.154 -17.959   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.820 -17.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.820 -15.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.487 -14.879   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      25.487 -13.339   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.152 -22.579   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.818 -21.809   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      21.486 -21.809   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.486 -20.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.819 -19.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.819 -17.959   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.486 -17.189   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      24.153 -17.189   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.817 -24.119   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.817 -22.579   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.483 -24.889   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
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   20                                                       
CONECT   20   19                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

View in JSmol

Synonyms

Value	Source
20-oxo-LTE(,4)	HMDB
6-(S-Cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoate	HMDB
6-(S-Cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₃H₃₅NO₆S

Average Mass

453.5920 Da

Monoisotopic Mass

453.21851 Da

IUPAC Name

(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid

Traditional Name

(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid

CAS Registry Number

Not Available

SMILES

N[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC=O)[C@@H](O)CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C23H35NO6S/c24-19(23(29)30)18-31-21(20(26)14-13-16-22(27)28)15-11-9-7-5-3-1-2-4-6-8-10-12-17-25/h2-5,7,9,11,15,17,19-21,26H,1,6,8,10,12-14,16,18,24H2,(H,27,28)(H,29,30)/b4-2-,5-3-,9-7+,15-11+/t19-,20+,21-/m1/s1

InChI Key

DXFWBOQUFGDWDP-HEZGWBLQSA-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 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-hydroxyacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
Imidolactam
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Phosphoric acid ester
Oxolane
Heteroaromatic compound
Azole
Imidazole
Carbothioic s-ester
Amino acid or derivatives
Thiocarboxylic acid ester
Secondary alcohol
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Azacycle
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Oxacycle
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Primary amine
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.66	ALOGPS
logP	0.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	2.39	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	137.92 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	128.36 m³·mol⁻¹	ChemAxon
Polarizability	50.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012642

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029164

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 20-Oxo-leukotriene E4 (NP0339081)

MOL for NP0339081 (20-Oxo-leukotriene E4)

3D MOL for NP0339081 (20-Oxo-leukotriene E4)

3D SDF for NP0339081 (20-Oxo-leukotriene E4)

3D-SDF for NP0339081 (20-Oxo-leukotriene E4)

PDB for NP0339081 (20-Oxo-leukotriene E4)

3D PDB for NP0339081 (20-Oxo-leukotriene E4)

SMILES for NP0339081 (20-Oxo-leukotriene E4)

INCHI for NP0339081 (20-Oxo-leukotriene E4)

Structure for NP0339081 (20-Oxo-leukotriene E4)

3D Structure for NP0339081 (20-Oxo-leukotriene E4)