MiMeDB: Showing metabocard for Delta(6)-trans,Delta(8)-cis-leukotriene B4 (MMDBc0033104)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:58 UTC

Update Date

2022-08-31 22:26:13 UTC

Metabolite ID

MMDBc0033104

Metabolite Identification

Common Name

Delta(6)-trans,Delta(8)-cis-leukotriene B4

Description

Delta(6)-trans,Delta(8)-cis-leukotriene B4 is an isomer of leukotriene B4. Leukotrienes are fatty signaling molecules. Leukotrienes are fatty signaling molecules. Leukotrienes are synthesized in the cell from arachidonic acid. The catalytic mechanism involves the insertion of an oxygen moiety at a specific position in the arachidonic acid backbone. [Wikipedia]

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241222342D          

 24 23  0  0  0  0            999 V2000
   -3.7344   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5910   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5524   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959   -0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248   -0.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -1.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5524   -0.5666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1620   -0.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -2.6292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0200   -1.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5910   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5524   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  0  0  0  0
 18  4  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3 20  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  9 16  1  0  0  0  0
 16 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  1  0  0  0
 18 19  1  1  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
  8  9  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033104

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCC\C=C/C[C@@H](O)\C=C\C=C/C=C/[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-/m1/s1

> <INCHI_KEY>
VNYSSYRCGWBHLG-GEWAPNICSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.82602535753441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8Z,10E,12R,14Z)-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>
102.98500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.971  -5.678   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.971  -7.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.637  -7.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.304  -5.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.970  -4.908   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.636  -5.678   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.303  -4.908   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.303  -3.368   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.031  -2.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.365  -0.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.698  -1.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.032  -0.288   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.700  -0.288   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.366  -1.058   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.366  -2.598   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.031  -1.058   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.302  -0.288   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.637  -4.908   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.637  -3.368   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.304  -7.218   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.970  -7.988   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.636  -7.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.303  -7.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.031  -7.218   0.000  0.00  0.00           C+0
CONECT    1   18    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2   20                                                       
CONECT    4   18    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7                                                       
CONECT    9   16    8                                                       
CONECT   10   16   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   14                                                       
CONECT   13   14                                                            
CONECT   14   12   13   15                                                  
CONECT   15   14                                                            
CONECT   16    9   10   17                                                  
CONECT   17   16                                                            
CONECT   18    1    4   19                                                  
CONECT   19   18                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
(5S,12R,6E,8Z,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
(5S,6E,8Z,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	ChEBI
(6E,8Z)-LTB4	ChEBI
5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-icosatetraenoic acid	ChEBI
Delta(6)-trans,Delta(8)-cis-LTB4	ChEBI
(5S,12R,6E,8Z,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate	Generator
(5S,6E,8Z,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Generator
5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-icosatetraenoate	Generator
Δ(6)-trans,δ(8)-cis-LTB4	Generator
Δ(6)-trans,δ(8)-cis-leukotriene b4	Generator
(5S,6E,8Z,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate	Generator

Molecular Formula

C₂₀H₃₂O₄

Average Mass

336.4657

Monoisotopic Mass

336.230059512

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C[C@@H](O)\C=C\C=C/C=C/[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-/m1/s1

InChI Key

VNYSSYRCGWBHLG-GEWAPNICSA-N

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
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:53027 )
leukotriene (CHEBI:53027 )
dihydroxy monocarboxylic acid (CHEBI:53027 )
polyunsaturated fatty acid (CHEBI:53027 )
hydroxy fatty acid (CHEBI:53027 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
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	39.83 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-7896000000-60973fb1d8ff05c73e4e	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0019000000-d06f0a12667843b97658	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4i-4497000000-49192078b0a92e5ed652	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9550000000-e2a30d40bfb9540f0c91	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0029000000-7cc4d5a37790281bbb77	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-2369000000-806fa56efb5d857c3921	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9350000000-bf1ddb92a7380f774742	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

9949656

PDB ID

Not Available

ChEBI ID

53027

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kull F, Ohlson E, Lind B, Haeggstrom JZ: Saccharomyces cerevisiae leukotriene A4 hydrolase: formation of leukotriene B4 and identification of catalytic residues. Biochemistry. 2001 Oct 23;40(42):12695-703. doi: 10.1021/bi011348p. [PubMed:11601994 ]
Huh WK, Falvo JV, Gerke LC, Carroll AS, Howson RW, Weissman JS, O'Shea EK: Global analysis of protein localization in budding yeast. Nature. 2003 Oct 16;425(6959):686-91. doi: 10.1038/nature02026. [PubMed:14562095 ]
Albuquerque CP, Smolka MB, Payne SH, Bafna V, Eng J, Zhou H: A multidimensional chromatography technology for in-depth phosphoproteome analysis. Mol Cell Proteomics. 2008 Jul;7(7):1389-96. doi: 10.1074/mcp.M700468-MCP200. Epub 2008 Apr 11. [PubMed:18407956 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]

Showing metabocard for Delta(6)-trans,Delta(8)-cis-leukotriene B4 (MMDBc0033104)

MOL for #<Metabolite:0x00007fecccbec1a0>

3D MOL for #<Metabolite:0x00007fecccbec1a0>

3D SDF for #<Metabolite:0x00007fecccbec1a0>

3D-SDF for #<Metabolite:0x00007fecccbec1a0>

PDB for #<Metabolite:0x00007fecccbec1a0>

3D PDB for #<Metabolite:0x00007fecccbec1a0>

SMILES for #<Metabolite:0x00007fecccbec1a0>

INCHI for #<Metabolite:0x00007fecccbec1a0>

Structure for #<Metabolite:0x00007fecccbec1a0>

3D Structure for #<Metabolite:0x00007fecccbec1a0>