ChemFOnt: Showing chemical card for (S)-3-Hydroxydodecanoyl-CoA (CFc000001997)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:46 UTC

Chemfont ID

CFc000001997

Molecule Identification

Common Name

(S)-3-Hydroxydodecanoyl-CoA

Definition

(S)-3-Hydroxydodecanoyl-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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-3-Hydroxydodecanoyl-coenzyme A	HMDB
(S)-3-Hydroxylauroyl-CoA	HMDB
(S)-3-Hydroxylauroyl-coenzyme A	HMDB

Chemical Formula

C₃₃H₅₈N₇O₁₈P₃S

Average Molecular Weight

965.836

Monoisotopic Molecular Weight

965.277188313

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxydodecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]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-3-({2-[(2-{[(3S)-3-hydroxydodecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

72059-49-5

SMILES

CCCCCCCCC[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=C(N)N=CN=C12

InChI Identifier

InChI=1S/C33H58N7O18P3S/c1-4-5-6-7-8-9-10-11-21(41)16-24(43)62-15-14-35-23(42)12-13-36-31(46)28(45)33(2,3)18-55-61(52,53)58-60(50,51)54-17-22-27(57-59(47,48)49)26(44)32(56-22)40-20-39-25-29(34)37-19-38-30(25)40/h19-22,26-28,32,41,44-45H,4-18H2,1-3H3,(H,35,42)(H,36,46)(H,50,51)(H,52,53)(H2,34,37,38)(H2,47,48,49)/t21-,22+,26+,27+,28?,32+/m0/s1

InChI Key

IJFLXRCJWPKGKJ-AGWWUHEJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(S)-3-hydroxyacyl 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
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
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
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Fatty acyl CoAs (C05262 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003936)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003936)

Source

Endogenous

Endogenous (HMDB: HMDB0003936)

Animal

Animal (HMDB: HMDB0003936)

Exogenous

Food

Food (HMDB: HMDB0003936)

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)

Exogenous (HMDB: HMDB0003936)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003936)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003936)
Fatty Acid Metabolism (PathBank: SMP0063589)
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids (PathBank: SMP0063640)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0087294)
Phospholipid Biosynthesis CL(12:0(3-OH)/12:0/12:0/12:0) (PathBank: SMP0122123)
Phospholipid Biosynthesis CL(12:0(3-OH)/15:0cycw5/12:0(3-OH)/15:0cycw5) (PathBank: SMP0122127)
Phospholipid Biosynthesis CL(12:0(3-OH)/17:0cycw7/12:0(3-OH)/17:0cycw7) (PathBank: SMP0122128)
Phospholipid Biosynthesis CL(12:0(3-OH)/17:0cycw7/12:0/12:0) (PathBank: SMP0122129)
Phospholipid Biosynthesis CL(12:0(3-OH)/i-19:0/12:0(3-OH)/i-19:0) (PathBank: SMP0122132)
Phospholipid Biosynthesis CL(15:0/12:0(3-OH)/15:0/12:0(3-OH)) (PathBank: SMP0122152)
Phospholipid Biosynthesis CL(18:1(9Z)/12:0(3-OH)/18:1(9Z)/12:0(3-OH)) (PathBank: SMP0122184)
Fatty Acid Metabolism (PathBank: SMP0002361)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0002368)
Fatty Acid Elongation (PathBank: SMP0121069)
Phospholipid Biosynthesis CL(16:1(9Z)/12:0(3-OH)/16:1(9Z)/12:0(3-OH)) (PathBank: SMP0122053)
Phospholipid Biosynthesis CL(10:0(3-OH)/12:0(3-OH)/10:0(3-OH)/12:0(3-OH)) (PathBank: SMP0122107)
Phospholipid Biosynthesis CL(10:0/12:0(3-OH)/10:0/12:0(3-OH)) (PathBank: SMP0122118)
Phospholipid Biosynthesis CL(12:0(3-OH)/10:0/12:0(3-OH)/10:0) (PathBank: SMP0122121)
Phospholipid Biosynthesis CL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/14:0(3-OH)) (PathBank: SMP0122124)
Phospholipid Biosynthesis CL(12:0/12:0(3-OH)/12:0/12:0) (PathBank: SMP0122135)
Phospholipid Biosynthesis CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) (PathBank: SMP0122140)
Phospholipid Biosynthesis CL(14:0/12:0(3-OH)/14:0/12:0(3-OH)) (PathBank: SMP0122149)
Phospholipid Biosynthesis CL(17:0cycw7/12:0(3-OH)/12:0/12:0) (PathBank: SMP0122171)
Phospholipid Biosynthesis CL(17:0cycw7/12:0(3-OH)/17:0cycw7/12:0(3-OH)) (PathBank: SMP0122172)
Phospholipid Biosynthesis CL(i-19:0/12:0(3-OH)/i-19:0/12:0(3-OH)) (PathBank: SMP0122201)
Fatty Acid Oxidation (Laurate) (PathBank: SMP0121349)
Phospholipid Biosynthesis CL(12:0(3-OH)/15:0/12:0(3-OH)/15:0) (PathBank: SMP0122126)
Phospholipid Biosynthesis CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z)) (PathBank: SMP0122130)
Phospholipid Biosynthesis CL(12:0(3-OH)/19:0cycw7/12:0(3-OH)/19:0cycw7) (PathBank: SMP0122131)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0063612)
Phospholipid Biosynthesis CL(16:0/12:0(3-OH)/16:0/12:0(3-OH)) (PathBank: SMP0122042)
Phospholipid Biosynthesis CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)) (PathBank: SMP0122120)
Phospholipid Biosynthesis CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0) (PathBank: SMP0122122)
Phospholipid Biosynthesis CL(12:0(3-OH)/14:0/12:0(3-OH)/14:0) (PathBank: SMP0122125)
Phospholipid Biosynthesis CL(19:0cycw7/12:0(3-OH)/12:0/12:0) (PathBank: SMP0122193)
Phospholipid Biosynthesis CL(19:0cycw7/12:0(3-OH)/19:0cycw7/12:0(3-OH)) (PathBank: SMP0122194)
Phospholipid Biosynthesis CL(i-19:0/12:0(3-OH)/12:0/12:0) (PathBank: SMP0122200)

Disease pathway

Very-Long-Chain Acyl-CoA Dehydrogenase Deficiency (VLCAD) (PathBank: SMP0120824)
Carnitine Palmitoyl Transferase Deficiency II (PathBank: SMP0120825)
Long-Chain-3-Hydroxyacyl-CoA Dehydrogenase Deficiency (LCHAD) (PathBank: SMP0120827)
Ethylmalonic Encephalopathy (HMDB: HMDB0003936)
Trifunctional Protein Deficiency (PathBank: SMP0120609)
Ethylmalonic Encephalopathy (PathBank: SMP0120696)
Carnitine Palmitoyl Transferase Deficiency I (PathBank: SMP0120822)
Long Chain Acyl-CoA Dehydrogenase Deficiency (LCAD) (PathBank: SMP0120604)
Medium Chain Acyl-CoA Dehydrogenase Deficiency (MCAD) (PathBank: SMP0120607)
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (PathBank: SMP0120740)
Glutaric Aciduria Type I (PathBank: SMP0000185)

Lipid metabolism pathway (HMDB: HMDB0003936)

Cellular process

Cell signaling (HMDB: HMDB0003936)

Biochemical process

Lipid transport (HMDB: HMDB0003936)

Role

Biological role

Energy source (HMDB: HMDB0003936)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003936)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.89 g/L	ALOGPS
logP	0.68	ALOGPS
logP	-3.5	ChemAxon
logS	-2.5	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	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	219.76 m³·mol⁻¹	ChemAxon
Polarizability	91.42 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

HMDB0003936

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023255

KNApSAcK ID

Not Available

Chemspider ID

389501

KEGG Compound ID

C05262

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440603

PDB ID

Not Available

ChEBI ID

27668

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Eaton, Simon; Bhuiyan, A. K. M. Jalal; Kler, Rajinder Singh; Turnbull, Douglass M.; Bartlett, Kim. Intramitochondrial control of the oxidation of hexadecanoate in skeletal muscle. A study of the acyl-CoA esters which accumulate during rat skeletal-muscle mitochondrial b-oxidation of [U-14C]hexadecanoate and [U-14C]hexadecanoyl-carnitine. Biochemical Journal (1993), 289(1), 161-8.

Showing chemical card for (S)-3-Hydroxydodecanoyl-CoA (CFc000001997)

MOL for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

3D MOL for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

3D SDF for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

3D-SDF for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

PDB for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

3D PDB for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

SMILES for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

INCHI for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

Structure for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)

3D Structure for CFc000001997 ((S)-3-Hydroxydodecanoyl-CoA)