ContaminantDB: 13E-Tetranor-16-oxo-16-CoA-LTE4

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-27 01:05:41 UTC

Update Date

2016-11-09 01:22:22 UTC

Accession Number

CHEM040956

Identification

Common Name

13E-Tetranor-16-oxo-16-CoA-LTE4

Class

Small Molecule

Description

13E-Tetranor-16-oxo-16-CoA-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. 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. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CoA-Omega-COOH-13E-tetranor-lte(,4)	HMDB
coenzyme A-Omega-COOH-13E-tetranor-lte(,4)	HMDB
6-[(2-Amino-2-carboxyethyl)sulfanyl]-16-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-5-hydroxy-16-oxohexadeca-7,9,11,13-tetraenoate	HMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-16-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5-hydroxy-16-oxohexadeca-7,9,11,13-tetraenoate	HMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-16-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5-hydroxy-16-oxohexadeca-7,9,11,13-tetraenoic acid	HMDB

Chemical Formula

C₄₀H₅₇N₈O₂₂P₃S₂

Average Molecular Mass

1158.972 g/mol

Monoisotopic Mass

1158.224 g/mol

CAS Registry Number

Not Available

IUPAC Name

6-[(2-amino-2-carboxyethyl)sulfanyl]-16-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-hydroxy-16-oxohexadeca-7,9,11,13-tetraenoic acid

Traditional Name

6-[(2-amino-2-carboxyethyl)sulfanyl]-16-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5-hydroxy-16-oxohexadeca-7,9,11,13-tetraenoic acid

SMILES

O[C@@H](CCCC(O)=O)[C@H](SC[C@@H](N)C(O)=O)\C=C\C=C\C=C/C=C/CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C40H61N8O22P3S2/c1-40(2,21-67-73(64,65)70-72(62,63)66-19-26-33(69-71(59,60)61)32(54)38(68-26)48-23-47-31-35(42)45-22-46-36(31)48)34(55)37(56)44-16-15-28(50)43-17-18-74-30(53)14-9-7-5-3-4-6-8-12-27(75-20-24(41)39(57)58)25(49)11-10-13-29(51)52/h3-9,12,22-27,32-34,38,49,54-55H,10-11,13-21,41H2,1-2H3,(H,43,50)(H,44,56)(H,51,52)(H,57,58)(H,62,63)(H,64,65)(H2,42,45,46)(H2,59,60,61)/p-4/b5-3-,6-4+,9-7+,12-8+/t24-,25+,26-,27-,32+,33+,34?,38-/m1/s1

InChI Key

FSCROZZUFXOEMF-AQSNFWIISA-J

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 3-enoyl chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 3-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Long-chain fatty acid
Cysteine or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Alpha-amino acid
Alpha-amino acid or derivatives
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Thia fatty acid
Hydroxy fatty acid
Alkyl phosphate
Imidolactam
Unsaturated fatty acid
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Fatty acid
Dicarboxylic acid or derivatives
Phosphoric acid ester
Azole
Oxolane
Imidazole
Heteroaromatic compound
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary alcohol
Amino acid
Amino acid or derivatives
Organoheterocyclic compound
Sulfenyl compound
Thioether
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Thiocarboxylic acid or derivatives
Azacycle
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Primary amine
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Primary aliphatic amine
Alcohol
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	1.09	ALOGPS
logP	-5.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	0.81	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	484.48 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	270.45 m³·mol⁻¹	ChemAxon
Polarizability	110.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900111000-fbe7d8ca06c255f41b9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900213000-1c184fd6342b04a91d6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900101000-4557ec133970e078e982	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05al-4900130200-27ab1d179ae2b65171fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5900120000-9afb266cd5047146a95e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057r-6900100000-c06630cfcbcfdc7f7452	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9200000002-5e8aa89d46b97c0b8017	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6900000011-339926c70e11abc0d06b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1301509000-e9461f5c2ff959c753e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-7900000000-e36543b35d0149a2576e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000002-bb7fbec8448039e1876d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-9001200002-e952e821b44d7e115a6c	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum