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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-12-20 20:20:54 UTC
HMDB IDHMDB0002057
Secondary Accession Numbers
  • HMDB02057
Metabolite Identification
Common NamePristanoyl-CoA
Description(R) Pristanoyl-CoA is converted by alpha-methylacyl-CoA racemase (E.C. 5.1.99.4) (S) pristanoyl-CoA, which is then degraded via peroxisomal beta-oxidation. Deficiency in this enzyme results in neuropathy, hypogonadism of adult onset; and in infant, defective bile acid synthesis has been observed. Pristanoyl-CoA is the substrate of propionyl-CoA C(2)-trimethyltridecanoyltransferase (E.C.2.3.1.154). It is the substrate of peroxisomal pristanoyl-CoA oxidase (E.C.1.3.3.6). A genetic disorder called Zellweger syndrome (OMIM: 214100 ), also known as neonatal adrenoleukodystrophy, NALD) is the result of a lack of pristanoyl-CoA oxidase, and the subsequent accumulation of phytanic acid and pristanic acid.
Structure
Thumb
Synonyms
ValueSource
3-Oxopristanoyl-CoAHMDB
3-Oxopristanoyl-coenzyme AHMDB
Pristanoyl CoAHMDB
Pristanoyl coenzyme AHMDB
Chemical FormulaC40H70N7O18P3S
Average Molecular Weight1062.006
Monoisotopic Molecular Weight1061.371088697
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-[(2,6,10,14-tetramethyl-3-oxopentadecanoyl)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-[(2,6,10,14-tetramethyl-3-oxopentadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCCC(C)CCCC(C)CCC(=O)C(C)C(=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/C40H70N7O18P3S/c1-24(2)10-8-11-25(3)12-9-13-26(4)14-15-28(48)27(5)39(53)69-19-18-42-30(49)16-17-43-37(52)34(51)40(6,7)21-62-68(59,60)65-67(57,58)61-20-29-33(64-66(54,55)56)32(50)38(63-29)47-23-46-31-35(41)44-22-45-36(31)47/h22-27,29,32-34,38,50-51H,8-21H2,1-7H3,(H,42,49)(H,43,52)(H,57,58)(H,59,60)(H2,41,44,45)(H2,54,55,56)/t25?,26?,27?,29-,32-,33-,34?,38-/m1/s1
InChI KeyNQFYRDGBRBDQQG-ILYQRJAASA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Diterpenoid
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Imidolactam
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Phosphoric acid ester
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Ketone
  • Sulfenyl compound
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP2.27ALOGPS
logP-0.2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity250.96 m³·mol⁻¹ChemAxon
Polarizability104.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901120200-04f35b8aa41f616287c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922130000-0659935dc59b615821beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-3824f840230847d12e66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02cu-9771430600-c7138f1d7d6112b33e64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5920210100-282d61b67409cca8a6f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-c6183c7d1b1b18061562View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Location
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Oxidation of Branched Chain Fatty AcidsThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022821
KNApSAcK IDNot Available
Chemspider ID390025
KEGG Compound IDC07297
BioCyc ID3-OXOPRISTANOYL-COA
BiGG ID2364529
Wikipedia LinkNot Available
METLIN ID6464
PubChem Compound441253
PDB IDNot Available
ChEBI ID28542
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Van Veldhoven PP, Croes K, Casteels M, Mannaerts GP: 2-methylacyl racemase: a coupled assay based on the use of pristanoyl-CoA oxidase/peroxidase and reinvestigation of its subcellular distribution in rat and human liver. Biochim Biophys Acta. 1997 Jul 12;1347(1):62-8. [PubMed:9233687 ]
  2. [No authors listed] [PubMed:106550687 ]
  3. Kuwert EK: [Passive immunization against rabies (author's transl)]. Immun Infekt. 1978 Apr;6(2):53-61. [PubMed:649182 ]

Only showing the first 10 proteins. There are 114 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Racemization of 2-methyl-branched fatty acid CoA esters. Responsible for the conversion of pristanoyl-CoA and C27-bile acyl-CoAs to their (S)-stereoisomers.
Gene Name:
AMACR
Uniprot ID:
Q9UHK6
Molecular weight:
43859.945
General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:
ACSL1
Uniprot ID:
P33121
Molecular weight:
77942.685
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Plays an important role in fatty acid metabolism in brain and the acyl-CoAs produced may be utilized exclusively for the synthesis of the brain lipid.
Gene Name:
ACSL6
Uniprot ID:
Q9UKU0
Molecular weight:
80609.765
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
ACOX2
Uniprot ID:
Q99424
Molecular weight:
76826.14
General function:
Involved in acyl-CoA binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q53GC8
Molecular weight:
40210.7
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225
General function:
Involved in acyltransferase activity
Specific function:
Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:
LPCAT1
Uniprot ID:
Q8NF37
Molecular weight:
59150.675
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Oxidizes the CoA-esters of 2-methyl-branched fatty acids (By similarity).
Gene Name:
ACOX3
Uniprot ID:
O15254
Molecular weight:
69574.075
General function:
Involved in acyltransferase activity
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis. Active against both saturated and unsaturated long-chain fatty acyl-CoAs.
Gene Name:
AGPAT6
Uniprot ID:
Q86UL3
Molecular weight:
52070.605

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 114 proteins in total.