Bovine Metabolome Database: Showing metabocard for 3-Oxohexadecanoyl-CoA (BMDB0006402)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:21:55 UTC

Update Date

2020-04-22 15:17:24 UTC

BMDB ID

BMDB0006402

Secondary Accession Numbers

BMDB06402

Metabolite Identification

Common Name

3-Oxohexadecanoyl-CoA

Description

3-Oxohexadecanoyl-CoA, also known as 3-ketopalmitoleoyl-CoA or 3-oxohexadec-9Z-enoyl-CoA, belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms. 3-Oxohexadecanoyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). 3-Oxohexadecanoyl-CoA exists in all living species, ranging from bacteria to humans. In cattle, 3-oxohexadecanoyl-CoA is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ketopalmitoleoyl-CoA	HMDB
3-Ketopalmitoleoyl-coenzyme A	HMDB
3-Ketopalmitoyl-CoA	HMDB
3-Ketopalmitoyl-coenzyme A	HMDB
3-oxo-cis-9-Hexadecenoyl-CoA	HMDB
3-oxo-cis-9-Hexadecenoyl-coenzyme A	HMDB
3-Oxohexadec-9Z-enoyl-CoA	HMDB
3-Oxohexadec-9Z-enoyl-coenzyme A	HMDB
3-Oxohexadec-cis-9-enoyl-CoA	HMDB
3-Oxohexadec-cis-9-enoyl-coenzyme A	HMDB
3-Oxopalmitoleoyl-CoA	HMDB
3-Oxopalmitoleoyl-coenzyme A	HMDB
3-Oxopalmitoyl-CoA	HMDB
3-Oxopalmitoyl-coenzyme A	HMDB

Chemical Formula

C₃₇H₆₄N₇O₁₈P₃S

Average Molecular Weight

1019.926

Monoisotopic Molecular Weight

1019.324138505

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

34619-89-1

SMILES

CCCCCCCCCCCCCC(=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=C(N)N=CN=C12

InChI Identifier

InChI=1S/C37H64N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-24,26,30-32,36,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t26-,30-,31-,32?,36-/m1/s1

InChI Key

NQMPLXPCRJOSHL-TZIIWEFPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated 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 3-oxoacyl 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
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
1,3-dicarbonyl compound
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.96	ALOGPS
logP	-1.2	ChemAxon
logS	-2.7	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	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	237.34 m³·mol⁻¹	ChemAxon
Polarizability	99.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane
Peroxisome

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fatty Acid Metabolism		Not Available
Fatty Acid Elongation in Mitochondria		Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids		Not Available