NP-MRD: Showing NP-Card for 20-hydroxy-ltb4 (NP0146626)

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Record Information

Version

2.0

Created at

2022-09-02 02:03:40 UTC

Updated at

2022-09-02 02:03:41 UTC

NP-MRD ID

NP0146626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-hydroxy-ltb4

Description

20-Hydroxy-leukotriene B4, also known as 20-OH-LTB4 or 20-hydroxy-LTB4, 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-hydroxy-leukotriene B4 is considered to be an eicosanoid lipid molecule. 20-Hydroxy-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 20-Hydroxy-leukotriene B4 can be biosynthesized from leukotriene B4; which is catalyzed by the enzyme leukotriene-b(4) omega-hydroxylase 1. The 20-hydroxy derivative of leukotriene B4. 20-hydroxy-ltb4 is found in Mus musculus. 20-hydroxy-ltb4 was first documented in 1985 (PMID: 3000366). In humans, 20-hydroxy-leukotriene B4 is involved in mefenamic acid action pathway (PMID: 11166796) (PMID: 3011899) (PMID: 12709426) (PMID: 9799565) (PMID: 8382231) (PMID: 8609415).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 57 56  0  0  0  0  0  0  0  0999 V2000
    6.9103   -2.5367    1.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5603   -1.6155    2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0746   -1.8562    3.4840 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8077   -0.3187    1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5713    0.3670    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8336   -0.3920    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    0.3938   -0.5468 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0732   -0.4326   -1.5730 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947    1.6376   -1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2202    2.4922   -1.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    2.1565   -1.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    1.8620   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0810    0.6931   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669    0.6108   -1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -0.5816   -0.6050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6713   -1.2202   -1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463   -0.0945    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781    0.8559    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0728    0.7020    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6946   -0.4677    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6189   -1.1766   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7249   -0.3005   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6689    0.2159    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4168   -0.8491    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5593   -1.6798    1.8126 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4403   -1.1323    4.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5563   -0.4908    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2909    0.3851    2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8019    1.3827    0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968    0.4924    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4476   -1.3561    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5003   -0.6210   -0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.4857    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828   -1.3825   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270    1.8621   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6789    3.3894   -2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6452    2.9888   -2.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    2.6520   -2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -0.0851   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8474    1.3715   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.3246   -0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.1987   -1.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    0.5371    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -0.8757    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142    1.7907   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328    1.4882   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9436   -1.1512    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -0.1591    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9649   -1.3589   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9692   -2.1324    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3157   -0.9188   -1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2706    0.5413   -1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0787    0.8703    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4118    0.8671   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1283   -1.4015    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0944   -0.3829    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9317   -2.5978    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 25 57  1  0
 24 55  1  0
 24 56  1  0
 23 53  1  0
 23 54  1  0
 22 51  1  0
 22 52  1  0
 21 49  1  0
 21 50  1  0
 20 47  1  0
 20 48  1  0
 19 46  1  0
 18 45  1  0
 17 43  1  0
 17 44  1  0
 15 41  1  1
 16 42  1  0
 14 40  1  0
 13 39  1  0
 12 38  1  0
 11 37  1  0
 10 36  1  0
  9 35  1  0
  7 33  1  1
  8 34  1  0
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 27  1  0
  4 28  1  0
  3 26  1  0
M  END


  Mrv0541 02231219112D          

 25 24  0  0  0  0            999 V2000
    4.8255  -12.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106  -12.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5290  -11.7210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2796  -11.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387  -12.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5256  -10.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623  -12.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423  -11.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8416  -11.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527  -12.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243  -12.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3555  -11.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -11.7525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0659  -12.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3487  -10.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958  -12.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -10.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958  -12.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243  -12.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657  -12.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2967  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210  -12.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414  -13.3953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  1  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  1  0  0  0
 16 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  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146626

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/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/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

> <INCHI_KEY>
PTJFJXLGRSTECQ-PSPARDEHSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.46273183675189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
2.688870060333332

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.843936486031904

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646345072403522

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1987619626600479

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
104.91369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-hydroxy-LTB4

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       9.008 -22.645   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.486 -22.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.321 -21.879   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.122 -21.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.646 -22.632   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.314 -20.358   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.783 -22.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.959 -21.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.438 -21.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.285 -22.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.099 -22.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.597 -21.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.768 -21.938   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.923 -22.600   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      15.584 -20.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.552 -22.692   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.768 -20.411   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.552 -24.232   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.768 -25.012   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.099 -24.232   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.444 -25.012   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.789 -24.238   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.154 -25.012   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.506 -24.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.851 -25.005   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    3                                                            
CONECT    7    4    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14   15                                                  
CONECT   13   11   16   17                                                  
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13   18                                                       
CONECT   17   13                                                            
CONECT   18   16   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
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoate	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate	ChEBI
20-Hydroxy-LTB4	ChEBI
20-OH-Leukotriene b4	ChEBI
20-OH-LTB4	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoic acid	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid	Generator
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoate	HMDB
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoic acid	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid	HMDB
20-Hydroxy LTB4	HMDB
20-Hydroxyleukotriene b4	HMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoate	HMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid	HMDB
5,12,20-THETE	HMDB
5,12,20-TriHETE	HMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	HMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	HMDB
Omega-hydroxy-LTB4	HMDB
W-Hydroxy-LTB4	HMDB
[S-[R,s-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoate	HMDB
[S-[R,s-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
20-Hydroxy-leukotriene b	HMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid, (S-(r,s-(e,Z,e,Z)))-isomer	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4651 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

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

Traditional Name

20-hydroxy-LTB4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/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/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

InChI Key

PTJFJXLGRSTECQ-PSPARDEHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

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
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:15646 )
Leukotrienes (C04853 )
Leukotrienes (LMFA03020018 )

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	4.22	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	104.91 m³·mol⁻¹	ChemAxon
Polarizability	40.46 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

HMDB0001509

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022663

KNApSAcK ID

Not Available

Chemspider ID

4444320

KEGG Compound ID

C04853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6287

PubChem Compound

5280745

PDB ID

Not Available

ChEBI ID

15646

Good Scents ID

Not Available

References

General References

Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. doi: 10.1016/s0022-510x(00)00474-3. [PubMed:11166796 ]
Goldman DW, Olson DM, Payan DG, Gifford LA, Goetzl EJ: Development of receptors for leukotriene B4 on HL-60 cells induced to differentiate by 1 alpha,25-dihydroxyvitamin D3. J Immunol. 1986 Jun 15;136(12):4631-6. [PubMed:3011899 ]
Berry KA, Borgeat P, Gosselin J, Flamand L, Murphy RC: Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem. 2003 Jul 4;278(27):24449-60. doi: 10.1074/jbc.M300856200. Epub 2003 Apr 22. [PubMed:12709426 ]
Jin R, Koop DR, Raucy JL, Lasker JM: Role of human CYP4F2 in hepatic catabolism of the proinflammatory agent leukotriene B4. Arch Biochem Biophys. 1998 Nov 1;359(1):89-98. doi: 10.1006/abbi.1998.0880. [PubMed:9799565 ]
Sumimoto H, Takeshige K, Minakami S: NAD+-dependent conversion of 20-OH-LTB4 to 20-COOH-LTB4 by a cell-free system of human polymorphonuclear leukocytes. Biochem Biophys Res Commun. 1985 Nov 15;132(3):864-70. doi: 10.1016/0006-291x(85)91887-x. [PubMed:3000366 ]
Bruijnzeel P, Storz E, van der Donk E, Bruijnzeel-Koomen C: Skin eosinophilia in patients with allergic asthma, patients with nonallergic asthma, and healthy controls. II: 20-Hydroxy-leukotriene B4 is a potent in vivo and in vitro eosinophil chemotactic factor in nonallergic asthma. J Allergy Clin Immunol. 1993 Feb;91(2):634-42. doi: 10.1016/0091-6749(93)90269-l. [PubMed:8382231 ]
Chilton-Lopez, Surette ME, Swan DD, Fonteh AN, Johnson MM, Chilton FH: Metabolism of gammalinolenic acid in human neutrophils. J Immunol. 1996 Apr 15;156(8):2941-7. [PubMed:8609415 ]
LOTUS database [Link]

Showing NP-Card for 20-hydroxy-ltb4 (NP0146626)

MOL for NP0146626 (20-hydroxy-ltb4)

3D MOL for NP0146626 (20-hydroxy-ltb4)

3D SDF for NP0146626 (20-hydroxy-ltb4)

3D-SDF for NP0146626 (20-hydroxy-ltb4)

PDB for NP0146626 (20-hydroxy-ltb4)

3D PDB for NP0146626 (20-hydroxy-ltb4)

SMILES for NP0146626 (20-hydroxy-ltb4)

INCHI for NP0146626 (20-hydroxy-ltb4)

Structure for NP0146626 (20-hydroxy-ltb4)

3D Structure for NP0146626 (20-hydroxy-ltb4)