Record Information
Version2.0
Creation Date2012-05-31 14:22:41 -0600
Update Date2015-06-03 17:19:07 -0600
Secondary Accession Numbers
  • ECMDB20010
Identification
Name:(3S)-3-Hydroxyadipyl-CoA
Description:(3s)-3-hydroxyadipyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • (3S)-3-Hydroxyadipyl-CoEnzyme A
Chemical Formula:C27H44N7O20P3S
Weight:Average: 911.659
Monoisotopic: 911.157467109
InChI Key:OTEACGAEDCIMBS-PXUUTJOASA-N
InChI:InChI=1S/C27H44N7O20P3S/c1-27(2,22(41)25(42)30-6-5-16(36)29-7-8-58-18(39)9-14(35)3-4-17(37)38)11-51-57(48,49)54-56(46,47)50-10-15-21(53-55(43,44)45)20(40)26(52-15)34-13-33-19-23(28)31-12-32-24(19)34/h12-15,20-22,26,35,40-41H,3-11H2,1-2H3,(H,29,36)(H,30,42)(H,37,38)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,15+,20+,21+,22?,26+/m0/s1
CAS number:Not Available
IUPAC Name:(4S)-6-({2-[(3-{[4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-hydroxy-6-oxohexanoic acid
Traditional IUPAC Name:(3S)-3-hydroxyadipyl-coa
SMILES:[H][C@](O)(CCC(O)=O)CC(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent(S)-3-hydroxyacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Monosaccharide
  • N-acyl-amine
  • Pyrimidine
  • N-substituted imidazole
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty amide
  • Primary aromatic amine
  • Fatty acid
  • Phosphoric acid ester
  • Imidolactam
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Azole
  • Amino acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.53 g/LALOGPS
logP-0.6ALOGPS
logP-4.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.84ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area428.14 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity194.86 m³·mol⁻¹ChemAxon
Polarizability81.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0891000250-95ee831c392fd0e68f20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0971100000-0cadf845dd290ebf5179View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2950000000-7709eb6393c101778ef8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0563-3911030342-c89e5aeeea16cfa04985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3910120010-0539537acd3c7a9cb785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-4dceb9b2f8705d7c11feView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID34002
HMDB IDHMDB12475
Pubchem Compound ID5282343
Kegg IDC14145
ChemSpider ID4445510
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Could possibly oxidize fatty acids using specific components
Gene Name:
paaF
Uniprot ID:
P76082
Molecular weight:
27237
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3- acetoacetyl-CoA + NADPH
Gene Name:
paaH
Uniprot ID:
P76083
Molecular weight:
51732
Reactions
(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3-acetoacetyl-CoA + NADPH.
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:
fadJ
Uniprot ID:
P77399
Molecular weight:
77072
Reactions
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Uniprot ID:
P21177
Molecular weight:
79593
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.