NP-MRD: Showing NP-Card for 20-COOH-leukotriene E4 (NP0339077)

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Record Information

Version

2.0

Created at

2024-09-11 19:34:49 UTC

Updated at

2024-09-11 19:34:49 UTC

NP-MRD ID

NP0339077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-COOH-leukotriene E4

Description

20-COOH-leukotriene E4, also known as 20-COOH-lte4, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, 20-COOH-leukotriene E4 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 20-COOH-leukotriene E4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Leukotriene E4 (LTE4) is a cysteinyl leukotriene. 20-COOH-leukotriene E4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4). Leukotrienes are eicosanoids. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 32 31  0  0  1  0            999 V2000
   11.3958  -12.5639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -12.5639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1583  -11.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3333  -11.8494    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9208  -11.1349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3333  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1583  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3958   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8083   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6333   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0458   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -11.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -11.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -12.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -13.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -13.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0458  -13.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -14.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958  -11.1349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6833  -11.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958   -8.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9208   -8.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833   -7.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1583  -13.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3333  -13.2784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -13.9929    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 30  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 22  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  1  0  0  0  0
 19 21  2  0  0  0  0
 22 23  1  1  0  0  0
 22 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
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END


  Mrv0541 02251208092D          

 32 31  0  0  1  0            999 V2000
   11.3958  -12.5639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -12.5639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1583  -11.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3333  -11.8494    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9208  -11.1349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3333  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1583  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3958   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8083   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6333   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0458   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -11.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -11.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -12.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -13.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8709  -13.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0458  -13.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -14.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958  -11.1349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6833  -11.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833  -10.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958   -9.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833   -8.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0958   -8.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9208   -8.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833   -7.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1583  -13.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3333  -13.2784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -13.9929    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 30  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 22  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  1  0  0  0  0
 19 21  2  0  0  0  0
 22 23  1  1  0  0  0
 22 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
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339077

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO7S/c24-18(23(30)31)17-32-20(19(25)13-12-16-22(28)29)14-10-8-6-4-2-1-3-5-7-9-11-15-21(26)27/h2-6,8,10,14,18-20,25H,1,7,9,11-13,15-17,24H2,(H,26,27)(H,28,29)(H,30,31)/b4-2-,5-3-,8-6+,14-10+/t18-,19+,20-/m1/s1

> <INCHI_KEY>
HVLRBLGTGJGVCX-RHSCJZQUSA-N

> <FORMULA>
C23H35NO7S

> <MOLECULAR_WEIGHT>
469.592

> <EXACT_MASS>
469.213423169

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.753598294928054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic acid

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.6968836436525127

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.32966346245196

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.383871530699766

> <JCHEM_PKA_STRONGEST_BASIC>
9.13006986317043

> <JCHEM_POLAR_SURFACE_AREA>
158.14999999999998

> <JCHEM_REFRACTIVITY>
129.28509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic 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      21.272 -23.453   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      19.732 -23.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.962 -22.119   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      17.422 -22.119   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      16.652 -20.785   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.422 -19.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.962 -19.452   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.732 -18.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.272 -18.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.042 -16.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.582 -16.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.352 -18.118   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.892 -18.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.662 -19.452   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.892 -20.785   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.662 -22.119   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.892 -23.453   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.662 -24.786   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.892 -26.120   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      24.352 -26.120   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      26.662 -27.454   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.112 -20.785   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.342 -22.119   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.342 -19.452   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.112 -18.118   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.342 -16.784   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.112 -15.451   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.652 -15.451   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.342 -14.117   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      18.962 -24.786   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      17.422 -24.786   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      19.732 -26.120   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
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   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    2   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Value	Source
20-COOH-LTE4	HMDB
6-(S-Cysteinyl)-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenedioate	HMDB
6-(S-Cysteinyl)-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenedioic acid	HMDB

Chemical Formula

C₂₃H₃₅NO₇S

Average Mass

469.5920 Da

Monoisotopic Mass

469.21342 Da

IUPAC Name

(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic acid

Traditional Name

(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H35NO7S/c24-18(23(30)31)17-32-20(19(25)13-12-16-22(28)29)14-10-8-6-4-2-1-3-5-7-9-11-15-21(26)27/h2-6,8,10,14,18-20,25H,1,7,9,11-13,15-17,24H2,(H,26,27)(H,28,29)(H,30,31)/b4-2-,5-3-,8-6+,14-10+/t18-,19+,20-/m1/s1

InChI Key

HVLRBLGTGJGVCX-RHSCJZQUSA-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 cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
S-alkyl-l-cysteine
Alpha-amino acid
D-alpha-amino acid
Tricarboxylic acid or derivatives
Hydroxy fatty acid
Thia fatty acid
Fatty acyl
Secondary alcohol
Amino acid
Carboxylic acid
Dialkylthioether
Sulfenyl compound
Thioether
Alcohol
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	0.18	ALOGPS
logP	0.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.15 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	129.29 m³·mol⁻¹	ChemAxon
Polarizability	51.75 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

HMDB0012634

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029159

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

53481508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 20-COOH-leukotriene E4 (NP0339077)

MOL for NP0339077 (20-COOH-leukotriene E4)

3D MOL for NP0339077 (20-COOH-leukotriene E4)

3D SDF for NP0339077 (20-COOH-leukotriene E4)

3D-SDF for NP0339077 (20-COOH-leukotriene E4)

PDB for NP0339077 (20-COOH-leukotriene E4)

3D PDB for NP0339077 (20-COOH-leukotriene E4)

SMILES for NP0339077 (20-COOH-leukotriene E4)

INCHI for NP0339077 (20-COOH-leukotriene E4)

Structure for NP0339077 (20-COOH-leukotriene E4)

3D Structure for NP0339077 (20-COOH-leukotriene E4)