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

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Record Information

Version

2.0

Created at

2024-09-11 19:22:47 UTC

Updated at

2024-09-11 19:22:47 UTC

NP-MRD ID

NP0339036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-Oxo-20-dihydroxy-leukotriene B4

Description

12-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. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes.

Structure

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
(5S,20,20)-Trihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoate	HMDB
(5S,20,20)-Trihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoic acid	HMDB
(5S,20,20)-Trihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoate	HMDB
(5S,20,20)-Trihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoic acid	HMDB
12-Keto-20,20-dihydroxy-leukotriene b(,4)	HMDB
12-oxo-20,20-Dihydroxy-leukotriene b(,4)	HMDB
Ox20dHLTB4	HMDB

Chemical Formula

C₂₀H₃₀O₆

Average Mass

366.4486 Da

Monoisotopic Mass

366.20424 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 Number

Not 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 Key

SBSLZLBZGOASJL-NZXMSVEXSA-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
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 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	2.7	ALOGPS
logP	2.51	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	105.16 m³·mol⁻¹	ChemAxon
Polarizability	40.44 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

HMDB0012551

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029118

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

53481458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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

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

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

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

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

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

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

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

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

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

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