NP-MRD: Showing NP-Card for 12(S)-Leukotriene B4 (NP0334125)

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Record Information

Version

2.0

Created at

2024-09-09 22:18:00 UTC

Updated at

2024-09-09 22:18:02 UTC

NP-MRD ID

NP0334125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12(S)-Leukotriene B4

Description

12(S)-Leukotriene B4 is an agonist of G-protein-coupled receptors for leukotriene B4 (LTB4), BLT1 and BLT2. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. 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. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 7649996 , 17623009 , 2866160 , 15866883 ) Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. 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. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004261606202D          

 34 33  0  0  1  0            999 V2000
   -3.2408   10.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263   10.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    9.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    5.5539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    8.0289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.9039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.9664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 18 21  1  6  0  0  0
 19 22  1  1  0  0  0
 23 20  2  0  0  0  0
 24 20  1  0  0  0  0
 25  6  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 14  1  0  0  0  0
 32 15  1  0  0  0  0
 18 33  1  6  0  0  0
 19 34  1  1  0  0  0
M  END


  Mrv1572004261606202D          

 34 33  0  0  1  0            999 V2000
   -3.2408   10.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263   10.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    9.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    5.5539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    8.0289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    6.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.9039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    5.5539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.9664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 18 21  1  6  0  0  0
 19 22  1  1  0  0  0
 23 20  2  0  0  0  0
 24 20  1  0  0  0  0
 25  6  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 14  1  0  0  0  0
 32 15  1  0  0  0  0
 18 33  1  6  0  0  0
 19 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334125

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6+,14-10+,15-11+/t18-,19+/m0/s1

> <INCHI_KEY>
VNYSSYRCGWBHLG-KQQZWENBSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.6599329828687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8E,10E,12S,14E)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
4.125548676999999

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720820347637158

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725928205

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749373349576958

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
102.98499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6E,8E,10E,12S,14E)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-16         0                                  
HETATM    1  C   UNK     0      -6.049  19.607   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.716  18.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.716  17.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.382  16.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.382  14.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.048  14.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.048  12.677   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.619   8.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.715  11.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.619   9.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.715  10.367   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.048   9.597   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -0.715  14.987   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.286   8.057   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.619   4.977   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.382  11.907   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.715   7.287   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.620   5.747   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.953  10.367   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.953   2.667   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.619  11.137   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.620   4.207   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9   25                                                  
CONECT    7    8   10   26                                                  
CONECT    8    7   11   27                                                  
CONECT    9    6   13   28                                                  
CONECT   10    7   14   29                                                  
CONECT   11    8   15   30                                                  
CONECT   12   16   17                                                       
CONECT   13    9   18                                                       
CONECT   14   10   18   31                                                  
CONECT   15   11   19   32                                                  
CONECT   16   12   19                                                       
CONECT   17   12   20                                                       
CONECT   18   13   14   21   33                                             
CONECT   19   15   16   22   34                                             
CONECT   20   17   23   24                                                  
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Value	Source
(5S,6E,8E,10E,12S,14E)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(5S,6E,8E,10E,12S,14E)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

(5S,6E,8E,10E,12S,14E)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6+,14-10+,15-11+/t18-,19+/m0/s1

InChI Key

VNYSSYRCGWBHLG-KQQZWENBSA-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
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.46	ALOGPS
logP	4.13	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	41.66 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

92223005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 12(S)-Leukotriene B4 (NP0334125)

MOL for NP0334125 (12(S)-Leukotriene B4)

3D MOL for NP0334125 (12(S)-Leukotriene B4)

3D SDF for NP0334125 (12(S)-Leukotriene B4)

3D-SDF for NP0334125 (12(S)-Leukotriene B4)

PDB for NP0334125 (12(S)-Leukotriene B4)

3D PDB for NP0334125 (12(S)-Leukotriene B4)

SMILES for NP0334125 (12(S)-Leukotriene B4)

INCHI for NP0334125 (12(S)-Leukotriene B4)

Structure for NP0334125 (12(S)-Leukotriene B4)

3D Structure for NP0334125 (12(S)-Leukotriene B4)