NP-MRD: Showing NP-Card for 10,11-Dihydro-20-trihydroxy-leukotriene B4 (NP0339023)

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Record Information

Version

2.0

Created at

2024-09-11 19:18:04 UTC

Updated at

2024-09-11 19:18:04 UTC

NP-MRD ID

NP0339023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,11-Dihydro-20-trihydroxy-leukotriene B4

Description

10,11-Dihydro-20-trihydroxy-leukotriene B4 belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. Thus, 10,11-dihydro-20-trihydroxy-leukotriene B4 is considered to be an eicosanoid lipid molecule. 10,11-Dihydro-20-trihydroxy-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. 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. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. Leukotrienes are eicosanoids. The PGs and TXs are collectively identified as prostanoids.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 27 26  0  0  1  0            999 V2000
   13.1398  -14.0922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5523  -13.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3773  -13.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7898  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6148  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0274  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524  -10.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0274  -10.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -9.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -8.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524   -7.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -6.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0274   -7.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1398  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023  -10.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148   -9.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148   -8.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0293   -8.7889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6003   -7.9639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7273   -7.6619    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 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  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  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END


  Mrv0541 02251208062D          

 27 26  0  0  1  0            999 V2000
   13.1398  -14.0922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5523  -13.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3773  -13.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7898  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6148  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0274  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524  -10.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0274  -10.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -9.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -8.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8524   -7.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2649   -6.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0274   -7.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1398  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148  -12.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023  -11.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023  -10.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148   -9.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9023   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3148   -8.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0293   -8.7889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6003   -7.9639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7273   -7.6619    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 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  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  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339023

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O7/c21-17(11-6-2-1-5-9-16-20(25,26)27)12-7-3-4-8-13-18(22)14-10-15-19(23)24/h2-4,6,8,13,17-18,21-22,25-27H,1,5,7,9-12,14-16H2,(H,23,24)/b4-3+,6-2-,13-8-/t17-,18-/m0/s1

> <INCHI_KEY>
LSVHZFZMMXHHBS-MNBASXMYSA-N

> <FORMULA>
C20H34O7

> <MOLECULAR_WEIGHT>
386.4798

> <EXACT_MASS>
386.230453442

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
43.310424800066926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12,20,20,20-pentahydroxyicosa-6,8,14-trienoic acid

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.130545767

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.420957272792192

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.584102176407992

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0842007383675827

> <JCHEM_POLAR_SURFACE_AREA>
138.45

> <JCHEM_REFRACTIVITY>
107.0276

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12,20,20,20-pentahydroxyicosa-6,8,14-trienoic 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      24.528 -26.305   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.298 -24.972   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.838 -24.972   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.608 -23.638   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.148 -23.638   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.918 -22.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.458 -22.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.228 -20.971   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.458 -19.637   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      29.918 -19.637   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      32.228 -18.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.458 -16.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.228 -15.636   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.458 -14.302   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      32.228 -12.968   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      29.918 -14.302   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      24.528 -23.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.988 -23.638   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.218 -22.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.988 -20.971   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.218 -19.637   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.988 -18.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.218 -16.969   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.988 -15.636   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      24.321 -16.406   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      21.654 -14.866   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      23.758 -14.302   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    2   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   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol

Synonyms

Value	Source
(5S,12R,20)-Pentahydroxy-(6Z,8E,14Z)-eicosatrienoate	HMDB
(5S,12R,20)-Pentahydroxy-(6Z,8E,14Z)-eicosatrienoic acid	HMDB
(5S,12R,20)-Pentahydroxy-(6Z,8E,14Z)-eicosatrienoic acid anion	HMDB

Chemical Formula

C₂₀H₃₄O₇

Average Mass

386.4798 Da

Monoisotopic Mass

386.23045 Da

IUPAC Name

(5R,6Z,8E,12R,14Z)-5,12,20,20,20-pentahydroxyicosa-6,8,14-trienoic acid

Traditional Name

(5R,6Z,8E,12R,14Z)-5,12,20,20,20-pentahydroxyicosa-6,8,14-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H34O7/c21-17(11-6-2-1-5-9-16-20(25,26)27)12-7-3-4-8-13-18(22)14-10-15-19(23)24/h2-4,6,8,13,17-18,21-22,25-27H,1,5,7,9-12,14-16H2,(H,23,24)/b4-3+,6-2-,13-8-/t17-,18-/m0/s1

InChI Key

LSVHZFZMMXHHBS-MNBASXMYSA-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 hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Ortho acid
Orthocarboxylic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	2.68	ALOGPS
logP	2.13	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	107.03 m³·mol⁻¹	ChemAxon
Polarizability	43.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012503

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029105

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

53481448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 10,11-Dihydro-20-trihydroxy-leukotriene B4 (NP0339023)

MOL for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

3D MOL for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

3D SDF for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

3D-SDF for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

PDB for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

3D PDB for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

SMILES for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

INCHI for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

Structure for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)

3D Structure for NP0339023 (10,11-Dihydro-20-trihydroxy-leukotriene B4)