NP-MRD: Showing NP-Card for 20-Oxo-leukotriene B4 (NP0339080)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 19:35:39 UTC

Updated at

2024-09-11 19:35:40 UTC

NP-MRD ID

NP0339080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-Oxo-leukotriene B4

Description

20-Oxo-leukotriene B4, also known as 20-oxo-LTB4 or LTB4-20-aldehyde, belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Thus, 20-oxo-leukotriene B4 is considered to be an eicosanoid lipid molecule. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. 20-Oxo-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 20-Oxo-leukotriene B4 exists in all living organisms, ranging from bacteria to humans. All mammalian cells except erythrocytes synthesize eicosanoids. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. 20-Oxo-leukotriene B4 was first documented in 1988 (PMID: 2836406). The PGs and TXs are collectively identified as prostanoids (PMID: 2155662) (PMID: 2549038).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 25 24  0  0  1  0            999 V2000
    9.1385  -19.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8530  -19.4965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5675  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2819  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9964  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7109  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7109  -20.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4254  -19.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8530  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1385  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4241  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7096  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -20.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8517  -20.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517  -18.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -17.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -17.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -16.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -15.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -15.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -14.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  9  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  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 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  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339080

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

> <INCHI_KEY>
LVLQYGYNBVIONY-PSPARDEHSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.599232303081564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.6466906596666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.509166952408247

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646344972587978

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749364051123648

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
103.725

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-aldehyde leukotriene B4

> <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  O   UNK     0      17.059 -35.623   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.392 -36.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.726 -35.623   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.060 -36.393   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.393 -35.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.727 -36.393   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      23.727 -37.933   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      25.061 -35.623   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.392 -37.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.059 -38.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.725 -37.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.391 -38.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.058 -37.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.724 -38.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.390 -37.933   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.057 -38.703   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.390 -36.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.057 -35.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.057 -34.083   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.390 -33.313   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.390 -31.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.724 -31.003   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.724 -29.463   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.058 -28.693   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.058 -27.153   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   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   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
20-Aldehyde leukotriene b4	ChEBI
20-oxo-LTB4	ChEBI
20Cho-LTB4	ChEBI
Leukotriene b4-20-aldehyde	ChEBI
LTB4-20-Aldehyde	ChEBI
20-Carboxyleukotriene b4	HMDB
20-Oxoleukotriene b4	HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4492 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid

Traditional Name

20-aldehyde leukotriene B4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

InChI Key

LVLQYGYNBVIONY-PSPARDEHSA-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 leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Alpha-hydrogen aldehyde
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:63979 )
leukotriene (CHEBI:63979 )
dihydroxy monocarboxylic acid (CHEBI:63979 )
hydroxyaldehyde (CHEBI:63979 )
polyunsaturated fatty acid (CHEBI:63979 )

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	3.53	ALOGPS
logP	2.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	103.72 m³·mol⁻¹	ChemAxon
Polarizability	39.6 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

HMDB0012641

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029163

KNApSAcK ID

Not Available

Chemspider ID

4952515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6449839

PDB ID

Not Available

ChEBI ID

63979

Good Scents ID

Not Available

References

General References

Gotoh Y, Sumimoto H, Minakami S: Formation of 20-oxoleukotriene B4 by an alcohol dehydrogenase isolated from human neutrophils. Biochim Biophys Acta. 1990 Mar 12;1043(1):52-6. doi: 10.1016/0005-2760(90)90109-b. [PubMed:2155662 ]
Sutyak J, Austen KF, Soberman RJ: Identification of an aldehyde dehydrogenase in the microsomes of human polymorphonuclear leukocytes that metabolizes 20-aldehyde leukotriene B4. J Biol Chem. 1989 Sep 5;264(25):14818-23. [PubMed:2549038 ]
Soberman RJ, Sutyak JP, Okita RT, Wendelborn DF, Roberts LJ 2nd, Austen KF: The identification and formation of 20-aldehyde leukotriene B4. J Biol Chem. 1988 Jun 15;263(17):7996-8002. [PubMed:2836406 ]

Showing NP-Card for 20-Oxo-leukotriene B4 (NP0339080)

MOL for NP0339080 (20-Oxo-leukotriene B4)

3D MOL for NP0339080 (20-Oxo-leukotriene B4)

3D SDF for NP0339080 (20-Oxo-leukotriene B4)

3D-SDF for NP0339080 (20-Oxo-leukotriene B4)

PDB for NP0339080 (20-Oxo-leukotriene B4)

3D PDB for NP0339080 (20-Oxo-leukotriene B4)

SMILES for NP0339080 (20-Oxo-leukotriene B4)

INCHI for NP0339080 (20-Oxo-leukotriene B4)

Structure for NP0339080 (20-Oxo-leukotriene B4)

3D Structure for NP0339080 (20-Oxo-leukotriene B4)