Np mrd loader

Showing NP-Card for 12-Oxo-20-dihydroxy-leukotriene B4 (NP0339036)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 19:22:47 UTC
Updated at2024-09-11 19:22:47 UTC
NP-MRD IDNP0339036
Secondary Accession NumbersNone
Natural Product Identification
Common Name12-Oxo-20-dihydroxy-leukotriene B4
Description12-Oxo-20-dihydroxy-leukotriene B4, also known as OX20DHLTB4, 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, 12-oxo-20-dihydroxy-leukotriene B4 is considered to be an eicosanoid lipid molecule. 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. 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. 12-Oxo-20-dihydroxy-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The PGs and TXs are collectively identified as prostanoids. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. It was first documented in 1984 (PMID: 6088485). Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes (PMID: 11413487) (PMID: 17623009) (PMID: 7649996) (PMID: 2853166).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)


  Mrv0541 02251208062D          

 26 25  0  0  1  0            999 V2000
   10.6248   -9.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6248  -10.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9103  -10.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -10.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -11.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -12.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -13.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -13.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -14.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -15.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4827  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1972  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6261  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3406  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3406  -14.2700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6261  -13.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -13.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -13.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7695  -12.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7695  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4840  -11.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -11.3824    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  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
  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 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  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
Download

3D MOL for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)

Download
3D SDF for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)

  Mrv0541 02251208062D          

 26 25  0  0  1  0            999 V2000
   10.6248   -9.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6248  -10.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9103  -10.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -10.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -11.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -12.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -13.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -13.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -14.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0537  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3393  -15.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7682  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4827  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1972  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9117  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6261  -15.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3406  -15.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3406  -14.2700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.6261  -13.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -13.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -13.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7695  -12.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7695  -11.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4840  -11.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -11.3824    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  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
  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  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 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  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339036

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,18-19,22-24H,1,3,9-11,14-16H2,(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1

> <INCHI_KEY>
SBSLZLBZGOASJL-NZXMSVEXSA-N

> <FORMULA>
C20H30O6

> <MOLECULAR_WEIGHT>
366.4486

> <EXACT_MASS>
366.204238692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.43790708536186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.507283140666666

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.562900140553307

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646344726110753

> <JCHEM_PKA_STRONGEST_BASIC>
-1.545246135801762

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
105.15659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,10E,14Z)-5,20,20-trihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)
Download
PDB for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)
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      19.833 -17.397   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      19.833 -18.937   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      18.499 -19.707   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      21.167 -19.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.167 -21.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.500 -22.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.500 -23.557   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.834 -24.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.834 -25.867   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.500 -26.637   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.500 -28.177   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      21.167 -28.947   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      23.834 -28.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.168 -28.177   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.501 -28.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.835 -28.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.169 -28.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.502 -28.177   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.502 -26.637   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      29.169 -25.867   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      31.836 -25.867   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.836 -24.327   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.170 -23.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.170 -22.017   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      34.503 -21.247   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      31.836 -21.247   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

Download
3D PDB for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)
Download
SMILES for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)
OC(O)CCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O
Download
INCHI for NP0339036 (12-Oxo-20-dihydroxy-leukotriene B4)
InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,18-19,22-24H,1,3,9-11,14-16H2,(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(5S,20,20)-Trihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoateHMDB
(5S,20,20)-Trihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoic acidHMDB
(5S,20,20)-Trihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoateHMDB
(5S,20,20)-Trihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoic acidHMDB
12-Keto-20,20-dihydroxy-leukotriene b(,4)HMDB
12-oxo-20,20-Dihydroxy-leukotriene b(,4)HMDB
Ox20dHLTB4HMDB
Chemical FormulaC20H30O6
Average Mass366.4486 Da
Monoisotopic Mass366.20424 Da
IUPAC Name(5R,6Z,8E,10E,14Z)-5,20,20-trihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional Name(5R,6Z,8E,10E,14Z)-5,20,20-trihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
OC(O)CCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,18-19,22-24H,1,3,9-11,14-16H2,(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1
InChI KeySBSLZLBZGOASJL-NZXMSVEXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentLeukotrienes  
Alternative Parents
Substituents
  • Leukotriene
    • 

  • Hydroxyeicosatetraenoic acid
    • 

  • Long-chain fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Keto fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Acryloyl-group
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Polyol
    • 

  • Carbonyl hydrate
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.7ALOGPS
logP2.51ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity105.16 m³·mol⁻¹ChemAxon
Polarizability40.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012551  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029118  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481458  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. doi: 10.1042/BJ20070289. [PubMed:17623009  ] 
  3. Wheelan P, Murphy RC: Metabolism of 6-trans-isomers of leukotriene B4 in cultured hepatoma cells and in human polymorphonuclear leukocytes. Identification of a delta 6-reductase metabolic pathway. J Biol Chem. 1995 Aug 25;270(34):19845-52. doi: 10.1074/jbc.270.34.19845. [PubMed:7649996  ] 
  4. Mita H, Yui Y, Yasueda H, Shida T: Isocratic determination of arachidonic acid 5-lipoxygenase products in human neutrophils by high-performance liquid chromatography. J Chromatogr. 1988 Sep 9;430(2):299-308. doi: 10.1016/s0378-4347(00)83165-5. [PubMed:2853166  ] 
  5. Shak S, Goldstein IM: Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. J Biol Chem. 1984 Aug 25;259(16):10181-7. [PubMed:6088485  ]