ChemFOnt: Showing chemical card for 3-hydroxyoctadecanoyl-CoA (CFc000008079)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:42 UTC

Chemfont ID

CFc000008079

Molecule Identification

Common Name

3-hydroxyoctadecanoyl-CoA

Definition

3-hydroxyoctadecanoyl-CoA is a human metabolite involved in the fatty acid elongation in mitochondria pathway. The enzyme long-chain-3-hydroxyacyl-CoA dehydrogenase catalyzes the conversion of 3-Oxododecanoyl-CoA to (S)-3-Hydroxydodecanoyl-CoA.3-hydroxyoctadecanoyl-CoA is an intermediate in fatty acid metabolism, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase and 3-hydroxyacyl-CoA dehydrogenase [EC 1.1.1.211-1.1.1.35]; 3-hydroxyoctadecanoyl-CoA is an intermediate in fatty acid elongation in mitochondria, the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74]. (KEGG).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxyoctadecanoyl-coenzyme A	HMDB
3-Hydroxystearoyl-CoA	HMDB
3-Hydroxystearoyl-coenzyme A	HMDB
beta-Hydroxystearoyl-CoA	HMDB
beta-Hydroxystearyl-CoA	HMDB

Chemical Formula

C₃₉H₆₆N₇O₁₈P₃S

Average Molecular Weight

1045.964

Monoisotopic Molecular Weight

1045.339788569

IUPAC Name

3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxyoctadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

Traditional Name

3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxyoctadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

CAS Registry Number

42578-91-6

SMILES

CCCCCCCCCCCCCCC[C@@H](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/C39H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-4/t27-,28-,32+,33+,34?,38-/m1/s1

InChI Key

WZMAIEGYXCOYSH-AJEXUEQGSA-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
Pentose phosphate
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
N-acyl-amine
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Primary amine
Organic oxide
Amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012715)
Membrane (HMDB: HMDB0012715)

Source

Exogenous

Exogenous (HMDB: HMDB0012715)

Endogenous

Endogenous (HMDB: HMDB0012715)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Oxidation (Steareate) (PathBank: SMP0121353)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	3.18	ALOGPS
logP	-0.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	395.18 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	242.88 m³·mol⁻¹	ChemAxon
Polarizability	103.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029169

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

53481517

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-hydroxyoctadecanoyl-CoA (CFc000008079)

MOL for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

3D MOL for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

3D SDF for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

3D-SDF for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

PDB for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

3D PDB for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

SMILES for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

INCHI for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

Structure for CFc000008079 (3-hydroxyoctadecanoyl-CoA)

3D Structure for CFc000008079 (3-hydroxyoctadecanoyl-CoA)