Record Information
Version3.6
Creation Date2007-05-23 12:12:07 UTC
Update Date2013-02-09 00:14:54 UTC
HMDB IDHMDB06497
Secondary Accession NumbersNone
Metabolite Identification
Common NameHeptadecanoyl CoA
DescriptionHeptadecanoyl CoA is an intermediate in lipid metabolism. The protein carnitine palmitoyltransferase II (mitochondrial) irreversibly transports heptadecanoate into the mitochondria. In the mitochondria, the enzyme acyl-CoA dehydrogenase [EC:1.3.99.3] catalyzes the irreversible catabolism of this metabolite to acetyl-CoA and propanoyl-CoA. In the cytosol, the enzyme carnitine O-palmitoyltransferase [EC:2.3.1.21] catalyzes the irreversible conversion of this metabolite to heptadecanoyl carnitine and the enzyme long-chain-fatty-acid-CoA ligase [EC:6.2.1.3] reversibly catalyzes the production of this metabolite from heptadecanoate. (BiGG database).
Structure
Thumb
Synonyms
  1. Heptadecanoate
  2. Heptadecanoic acid
  3. Heptadecanoic acid coa
  4. Heptadecanoyl coenzyme A
  5. Heptadecanoyl-coA
  6. Heptadecanoyl-coenzyme a
  7. Heptadecyl-coA
  8. Heptadecyl-coenzyme a
  9. Margaric acid coa
  10. Margaroyl coenzyme A
  11. N-Heptadecanoate
  12. N-Heptadecanoic acid
  13. N-Heptadecanoic acid coenzyme a
  14. S-Heptadecanoate
  15. S-Heptadecanoate coenzyme A
  16. S-Heptadecanoate-coenzyme a
  17. S-Heptadecanoic acid
  18. S-Heptadecanoyl CoA
  19. S-Heptadecanoyl coenzyme A
Chemical FormulaC38H68N7O17P3S
Average Molecular Weight1019.97
Monoisotopic Molecular Weight1019.360524011
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-[(2-{[2-(heptadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number3546-17-6
SMILES
CCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/t27-,31-,32-,33+,37-/m1/s1
InChI KeyDRABUZIHHACUPI-DUPKZGIXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct ParentAcyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
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 solubility1.23 g/LALOGPS
logP2.61ALOGPS
logP-0.051ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count17ChemAxon
hydrogen donor count9ChemAxon
polar surface area363.63ChemAxon
rotatable bond count35ChemAxon
refractivity241.25ChemAxon
polarizability102.54ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023941
KNApSAcK IDNot Available
Chemspider ID2339497
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2415330
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06497
Metagene LinkHMDB06497
METLIN IDNot Available
PubChem Compound3082004
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 173 proteins in total.

Enzymes

Gene Name:
FASN
Uniprot ID:
P49327
Gene Name:
ACAA1
Uniprot ID:
P09110
Gene Name:
PLA2G5
Uniprot ID:
P39877
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Gene Name:
CLC
Uniprot ID:
Q05315
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Gene Name:
ACOX1
Uniprot ID:
Q15067
Gene Name:
ACOX2
Uniprot ID:
Q99424
Gene Name:
ACOX3
Uniprot ID:
O15254
Gene Name:
PNLIP
Uniprot ID:
P16233
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
LIPF
Uniprot ID:
P07098
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
DGAT1
Uniprot ID:
O75907
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Gene Name:
LPL
Uniprot ID:
P06858
Gene Name:
SCD
Uniprot ID:
O00767
Gene Name:
CES1
Uniprot ID:
P23141
Gene Name:
CES2
Uniprot ID:
O00748
Gene Name:
SOAT2
Uniprot ID:
O75908
Gene Name:
SOAT1
Uniprot ID:
P35610
Gene Name:
BCHE
Uniprot ID:
P06276
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Gene Name:
ACYP2
Uniprot ID:
P14621
Gene Name:
ACYP1
Uniprot ID:
P07311

Transporters

Only showing the first 50 proteins. There are 173 proteins in total.