ContaminantDB: 16(S)-Hydroxy-18-oxo-18-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 01:05:47 UTC

Update Date

2016-11-09 01:22:22 UTC

Accession Number

CHEM040961

Identification

Common Name

16(S)-Hydroxy-18-oxo-18-CoA-LTE4

Class

Small Molecule

Description

16(S)-hydroxy-18-oxo-18-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-18-COOH-16(S)-OH-Dinor-lte(,4)	HMDB
coenzyme A-18-COOH-16(S)-OH-Dinor-lte(,4)	HMDB
6-[(2-Amino-2-carboxyethyl)sulfanyl]-18-({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)-5,16-dihydroxy-18-oxooctadeca-7,9,11-trienoate	HMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-18-({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)-5,16-dihydroxy-18-oxooctadeca-7,9,11-trienoate	HMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-18-({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)-5,16-dihydroxy-18-oxooctadeca-7,9,11-trienoic acid	HMDB

Chemical Formula

C₄₂H₆₃N₈O₂₃P₃S₂

Average Molecular Mass

1205.041 g/mol

Monoisotopic Mass

1204.266 g/mol

CAS Registry Number

Not Available

IUPAC Name

6-[(2-amino-2-carboxyethyl)sulfanyl]-18-{[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}-5,16-dihydroxy-18-oxooctadeca-7,9,11-trienoic acid

Traditional Name

6-[(2-amino-2-carboxyethyl)sulfanyl]-18-({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)-5,16-dihydroxy-18-oxooctadeca-7,9,11-trienoic acid

SMILES

O[C@@H](CCC\C=C/C=C/C=C/[C@@H](SC[C@@H](N)C(O)=O)[C@@H](O)CCCC(O)=O)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/C42H67N8O23P3S2/c1-42(2,22-70-76(67,68)73-75(65,66)69-20-28-35(72-74(62,63)64)34(57)40(71-28)50-24-49-33-37(44)47-23-48-38(33)50)36(58)39(59)46-16-15-30(53)45-17-18-77-32(56)19-25(51)11-8-6-4-3-5-7-9-13-29(78-21-26(43)41(60)61)27(52)12-10-14-31(54)55/h3-5,7,9,13,23-29,34-36,40,51-52,57-58H,6,8,10-12,14-22,43H2,1-2H3,(H,45,53)(H,46,59)(H,54,55)(H,60,61)(H,65,66)(H,67,68)(H2,44,47,48)(H2,62,63,64)/p-4/b4-3-,7-5+,13-9+/t25-,26+,27-,28+,29+,34-,35-,36?,40+/m0/s1

InChI Key

APLMMNVXTIRDHJ-RWNJKCKMSA-J

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic 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 fatty acyl 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
Octadecanoid
Long-chain fatty acid
Cysteine or derivatives
Glycosyl compound
N-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Hydroxy fatty acid
Monoalkyl phosphate
Thia fatty acid
Fatty acid
Imidolactam
Dicarboxylic acid or derivatives
Alkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Unsaturated fatty acid
Phosphoric acid ester
Pyrimidine
Imidazole
Oxolane
Azole
Heteroaromatic compound
Amino acid
Secondary alcohol
Thiocarboxylic acid ester
Carbothioic s-ester
Amino acid or derivatives
Dialkylthioether
Sulfenyl compound
Oxacycle
Thioether
Carboximidic acid
Azacycle
Thiocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Organic 1,3-dipolar compound
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organic oxide
Primary aliphatic amine
Primary amine
Amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organosulfur compound
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	0.66 g/L	ALOGPS
logP	0.61	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	24	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	504.71 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	280.05 m³·mol⁻¹	ChemAxon
Polarizability	117.94 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	splash10-0079-0900020000-609cf2277ad9241c2533	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900132100-4c3fcff31ad524af5cca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010100-ffc4802e973813a51d38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053i-2910220210-1df2730d53c4f376c837	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-3900110000-eac417ba621b594418fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057r-6900100000-602f2b8c1d70dec2225c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-1960000000-0fc3396c373858e61c19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-8ddf66b722f80d241a4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zi9-9800200100-d49243b6758d54febd6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9400000002-80f1dd8d1cc1d942f01b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-4900000001-ad31281f5eb63feee8e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1212302900-6944a696aa835931dbe5	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