NP-MRD: Showing NP-Card for omega-Carboxy-trinor-leukotriene B4 (NP0339158)

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Record Information

Version

2.0

Created at

2024-09-11 19:58:07 UTC

Updated at

2024-09-11 19:58:08 UTC

NP-MRD ID

NP0339158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

omega-Carboxy-trinor-leukotriene B4

Description

Omega-Carboxy-trinor-leukotriene B4, also known as omega-COOH-dinor-LTB(,4), 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. Omega-Carboxy-trinor-leukotriene B4 is an extremely weak basic (essentially neutral) compound (based on its pKa). The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. Leukotrienes are eicosanoids. All mammalian cells except erythrocytes synthesize eicosanoids. 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. The PGs and TXs are collectively identified as prostanoids. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208152D          

 24 23  0  0  1  0            999 V2000
   20.1544  -13.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7419  -12.4363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9169  -12.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5044  -11.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6794  -11.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3369  -12.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6794  -12.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6521  -12.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1544  -11.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7419  -11.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9169  -11.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5044  -10.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8543  -10.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4418   -9.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6168   -9.5784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2043  -10.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2043   -8.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3793   -8.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9668   -8.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3793   -7.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9668   -6.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3793   -6.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2043   -6.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9668   -5.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  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
  6  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  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
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339158

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O6/c19-15(11-6-3-7-13-17(21)22)9-4-1-2-5-10-16(20)12-8-14-18(23)24/h1-6,9-10,15-16,19-20H,7-8,11-14H2,(H,21,22)(H,23,24)/b2-1+,6-3-,9-4+,10-5-/t15-,16+/m1/s1

> <INCHI_KEY>
XWRIIHRGMKHPHN-LLVPEOCGSA-N

> <FORMULA>
C18H26O6

> <MOLECULAR_WEIGHT>
338.3954

> <EXACT_MASS>
338.172938564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.628023350913764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,7S,8E,10E,12Z,14R)-7,14-dihydroxyoctadeca-4,8,10,12-tetraenedioic acid

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
1.9161695819999995

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.945251760614849

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.343181863916477

> <JCHEM_PKA_STRONGEST_BASIC>
-1.274937757960764

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
95.44839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7S,8E,10E,12Z,14R)-7,14-dihydroxyoctadeca-4,8,10,12-tetraenedioic 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      37.622 -24.548   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      36.852 -23.214   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.312 -23.214   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.542 -21.881   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.002 -21.881   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.362 -22.988   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      33.002 -24.095   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      31.084 -22.988   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      37.622 -21.881   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.852 -20.547   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.312 -20.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.542 -19.213   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.461 -19.213   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.691 -17.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.151 -17.880   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      28.381 -19.213   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      28.381 -16.546   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.841 -16.546   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.071 -15.212   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.841 -13.879   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.071 -12.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.841 -11.211   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      28.381 -11.211   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.071  -9.877   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
7R,14S-Dihydroxy-1,18-octadec-4,12Z,8,10E-tetraendioate	HMDB
7R,14S-Dihydroxy-1,18-octadec-4,12Z,8,10E-tetraendioic acid	HMDB
7R,14S-Dihydroxy-1,18-octadec-4,12Z,8,10E-tetraendioic acid anion	HMDB
Omega-COOH-dinor-LTB(,4)	HMDB
(7S,8E,10E,12Z,14R)-7,14-Dihydroxyoctadeca-4,8,10,12-tetraenedioate	Generator

Chemical Formula

C₁₈H₂₆O₆

Average Mass

338.3954 Da

Monoisotopic Mass

338.17294 Da

IUPAC Name

(4Z,7S,8E,10E,12Z,14R)-7,14-dihydroxyoctadeca-4,8,10,12-tetraenedioic acid

Traditional Name

(4Z,7S,8E,10E,12Z,14R)-7,14-dihydroxyoctadeca-4,8,10,12-tetraenedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H26O6/c19-15(11-6-3-7-13-17(21)22)9-4-1-2-5-10-16(20)12-8-14-18(23)24/h1-6,9-10,15-16,19-20H,7-8,11-14H2,(H,21,22)(H,23,24)/b2-1+,6-3-,9-4+,10-5-/t15-,16+/m1/s1

InChI Key

XWRIIHRGMKHPHN-LLVPEOCGSA-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	2.3	ALOGPS
logP	1.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-1.3	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	13	ChemAxon
Refractivity	95.45 m³·mol⁻¹	ChemAxon
Polarizability	36.63 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

HMDB0013032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029258

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

53481589

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for omega-Carboxy-trinor-leukotriene B4 (NP0339158)

MOL for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

3D MOL for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

3D SDF for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

3D-SDF for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

PDB for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

3D PDB for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

SMILES for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

INCHI for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

Structure for NP0339158 (omega-Carboxy-trinor-leukotriene B4)

3D Structure for NP0339158 (omega-Carboxy-trinor-leukotriene B4)