NP-MRD: Showing NP-Card for 20-COOH-10,11-dihydro-LTB4 (NP0339076)

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Record Information

Version

2.0

Created at

2024-09-11 19:34:33 UTC

Updated at

2024-09-11 19:34:34 UTC

NP-MRD ID

NP0339076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-COOH-10,11-dihydro-LTB4

Description

20-COOH-10,11-dihydro-LTB4 belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 20-COOH-10,11-dihydro-LTB4 is considered to be an eicosanoid lipid molecule. 20-COOH-10,11-dihydro-LTB4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 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. All mammalian cells except erythrocytes synthesize eicosanoids. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Leukotrienes are eicosanoids. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 26 25  0  0  1  0            999 V2000
    9.6093  -14.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218  -13.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8468  -13.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2593  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -10.6689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4968  -10.6689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -7.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968   -7.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -10.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093   -8.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -7.8110    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  2  0  0  0  0
M  END


  Mrv0541 02251208092D          

 26 25  0  0  1  0            999 V2000
    9.6093  -14.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218  -13.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8468  -13.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2593  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -10.6689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4968  -10.6689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -7.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968   -7.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -10.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093   -8.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -7.8110    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  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339076

> <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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/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/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1

> <INCHI_KEY>
BCZGHMCTSJAJRR-NSBXBVANSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
41.85245400766139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.0113211086666665

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.8699831562007905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.267376576220767

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0842016937541343

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
103.6878

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic 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      17.937 -26.584   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.707 -25.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.247 -25.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.017 -23.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.557 -23.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.327 -22.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.867 -22.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.637 -21.249   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.867 -19.915   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      23.327 -19.915   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.637 -18.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.867 -17.248   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.637 -15.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.867 -14.581   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.637 -13.247   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.327 -14.581   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.937 -23.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.397 -23.916   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.627 -22.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.397 -21.249   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.627 -19.915   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.397 -18.582   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.627 -17.248   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.397 -15.914   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.937 -15.914   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      15.627 -14.581   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                                                  
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,12R)-Dihydroxy-(6Z,8E,14Z)-eicosatrien-1,20-dicarboxylic acid anion	HMDB
10,11-Dihydro-20-COOH-leukotriene b(,4)	HMDB
20-Carboxy-10,11-dihydro-LTB(,4)	HMDB

Chemical Formula

C₂₀H₃₂O₆

Average Mass

368.4645 Da

Monoisotopic Mass

368.21989 Da

IUPAC Name

(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

Traditional Name

(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic 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

InChI Identifier

InChI=1S/C20H32O6/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/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1

InChI Key

BCZGHMCTSJAJRR-NSBXBVANSA-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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
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	3.17	ALOGPS
logP	3.01	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	103.69 m³·mol⁻¹	ChemAxon
Polarizability	41.85 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

HMDB0012633

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029158

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

53481507

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 20-COOH-10,11-dihydro-LTB4 (NP0339076)

MOL for NP0339076 (20-COOH-10,11-dihydro-LTB4)

3D MOL for NP0339076 (20-COOH-10,11-dihydro-LTB4)

3D SDF for NP0339076 (20-COOH-10,11-dihydro-LTB4)

3D-SDF for NP0339076 (20-COOH-10,11-dihydro-LTB4)

PDB for NP0339076 (20-COOH-10,11-dihydro-LTB4)

3D PDB for NP0339076 (20-COOH-10,11-dihydro-LTB4)

SMILES for NP0339076 (20-COOH-10,11-dihydro-LTB4)

INCHI for NP0339076 (20-COOH-10,11-dihydro-LTB4)

Structure for NP0339076 (20-COOH-10,11-dihydro-LTB4)

3D Structure for NP0339076 (20-COOH-10,11-dihydro-LTB4)