ChemFOnt: Showing chemical card for 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid (CFc000042906)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:40 UTC

Chemfont ID

CFc000042906

Molecule Identification

Common Name

5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid

Definition

5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid, also known as LTD4 or Leukotriene D 4, is classified as a member of the Leukotrienes. Leukotrienes 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. 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid is considered to be practically insoluble (in water) and acidic. 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid is an eicosanoid lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀N₂O₆S

Average Molecular Weight

496.66

Monoisotopic Molecular Weight

496.260707712

IUPAC Name

(5S,6R,7E,9E)-6-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid

Traditional Name

(5S,6R,7E,9E)-6-{[2-amino-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid

CAS Registry Number

73836-78-9

SMILES

[H]C(CCCCC)=C([H])CC([H])=C([H])C(\[H])=C(/[H])\C(\[H])=C(/[H])[C@@]([H])(SCC([H])(N)C(O)=NCC(O)=O)[C@@]([H])(O)CCCC(O)=O

InChI Identifier

InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6?,10-9?,12-11+,16-13+/t20?,21-,22+/m0/s1

InChI Key

YEESKJGWJFYOOK-DRETYUQKSA-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
Alpha-dipeptide
Alpha peptide
Long-chain fatty acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Thia fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062494)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0062494)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	1.15	ALOGPS
logP	1.47	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.44 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	140.94 m³·mol⁻¹	ChemAxon
Polarizability	56.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023105

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leukotriene D4

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid (CFc000042906)

MOL for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

3D MOL for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

3D SDF for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

3D-SDF for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

PDB for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

3D PDB for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

SMILES for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

INCHI for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

Structure for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)

3D Structure for CFc000042906 (5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid)