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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:12 UTC
Update Date2021-09-14 15:16:00 UTC
HMDB IDHMDB0060392
Secondary Accession Numbers
  • HMDB60392
Metabolite Identification
Common Name5-Carboxy-2-pentenoyl-CoA
Description5-Carboxy-2-pentenoyl-CoA, also known as (e)-3,4-dehydroadipoyl-CoA or 2,3-didehydroadipyl-CoA, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Thus, 5-carboxy-2-pentenoyl-CoA is considered to be a fatty ester lipid molecule. 5-Carboxy-2-pentenoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866054
Synonyms
ValueSource
(e)-3,4-Dehydroadipoyl-CoAChEBI
2,3-Didehydroadipyl-CoAKegg
Chemical FormulaC27H42N7O19P3S
Average Molecular Weight893.644
Monoisotopic Molecular Weight893.146902423
IUPAC Name(4E)-6-[(2-{3-[(2R)-3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-6-oxohex-4-enoic acid
Traditional Nametrans-2,3-didehydroadipoyl-coa
CAS Registry NumberNot Available
SMILES
O[C@H](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)C(=O)NCCC(=O)NCCSC(=O)\C=C\CCC(O)=O
InChI Identifier
InChI=1S/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b6-4+/t15-,20-,21-,22+,26-/m1/s1
InChI KeyZFXICKRXPZTFPB-KCQRSJHASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Hydroxybenzoic acid
  • Monocyclic monoterpenoid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.97 g/LALOGPS
logP10(-0.21) g/LALOGPS
logP10(-6) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity193.4 m³·mol⁻¹ChemAxon
Polarizability77.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB030295
KNApSAcK IDNot Available
Chemspider ID21865675
KEGG Compound IDC14144
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24798711
PDB IDNot Available
ChEBI ID49295
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
5-Carboxy-2-pentenoyl-CoA + Water → (3S)-3-Hydroxyadipyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular weight:
31387.085
Reactions
5-Carboxy-2-pentenoyl-CoA + Water → (3S)-3-Hydroxyadipyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
5-Carboxy-2-pentenoyl-CoA + Water → (3S)-3-Hydroxyadipyl-CoAdetails