Human Metabolome Database Version 3.5

Showing metabocard for Heptadecanoyl CoA (HMDB06497)

Record Information
Version 3.5
Creation Date 2007-05-23 06:12:07 -0600
Update Date 2013-02-08 17:14:54 -0700
HMDB ID HMDB06497
Secondary Accession Numbers None
Metabolite Identification
Common Name Heptadecanoyl CoA
Description Heptadecanoyl 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C38H68N7O17P3S
Average Molecular Weight 1019.97
Monoisotopic Molecular Weight 1019.360524011
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 Number 3546-17-6
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 Key DRABUZIHHACUPI-DUPKZGIXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl 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 Parent Acyl CoAs
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.23 g/L ALOGPS
LogP 2.61 ALOGPS
LogP -0.051 ChemAxon
LogS -2.92 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 363.63 A2 ChemAxon
Rotatable Bond Count 35 ChemAxon
Refractivity 241.25 ChemAxon
Polarizability 102.54 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023941
KNApSAcK ID Not Available
Chemspider ID 2339497 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID 2415330 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06497 Link_out
Metagene Link HMDB06497 Link_out
METLIN ID Not Available
PubChem Compound 3082004 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 172 enzymes in total.

Name: 3-ketoacyl-CoA thiolase, mitochondrial
Reactions: Not Available
Gene Name: ACAA2
Uniprot ID: P42765 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty acid synthase
Reactions: Not Available
Gene Name: FASN
Uniprot ID: P49327 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions: Not Available
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions: Not Available
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
Reactions: Not Available
Gene Name: ALDH6A1
Uniprot ID: Q02252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside-binding soluble lectin 13
Reactions: Not Available
Gene Name: LGALS13
Uniprot ID: Q9UHV8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIA secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G12A
Uniprot ID: Q9BZM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions: Not Available
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2, membrane associated
Reactions: Not Available
Gene Name: PLA2G2A
Uniprot ID: P14555 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADL
Uniprot ID: P28330 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Short-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADS
Uniprot ID: P16219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Medium-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADM
Uniprot ID: P11310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 1
Reactions: Not Available
Gene Name: ACOX1
Uniprot ID: Q15067 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 2
Reactions: Not Available
Gene Name: ACOX2
Uniprot ID: Q99424 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Isovaleryl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: IVD
Uniprot ID: P26440 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 3
Reactions: Not Available
Gene Name: ACOX3
Uniprot ID: O15254 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutaryl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: GCDH
Uniprot ID: Q92947 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic triacylglycerol lipase
Reactions: Not Available
Gene Name: PNLIP
Uniprot ID: P16233 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inactive pancreatic lipase-related protein 1
Reactions: Not Available
Gene Name: PNLIPRP1
Uniprot ID: P54315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 3
Reactions: Not Available
Gene Name: PNPLA3
Uniprot ID: Q9NST1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastric triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPF
Uniprot ID: P07098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Endothelial lipase
Reactions: Not Available
Gene Name: LIPG
Uniprot ID: Q9Y5X9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: DGAT1
Uniprot ID: O75907 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 2
Reactions: Not Available
Gene Name: PNLIPRP2
Uniprot ID: P54317 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
Reactions: Not Available
Gene Name: BCKDHB
Uniprot ID: P21953 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
Reactions: Not Available
Gene Name: BCKDHA
Uniprot ID: P12694 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoprotein lipase
Reactions: Not Available
Gene Name: LPL
Uniprot ID: P06858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA desaturase
Reactions: Not Available
Gene Name: SCD
Uniprot ID: O00767 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit alpha, mitochondrial
Reactions: Not Available
Gene Name: HADHA
Uniprot ID: P40939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions: Not Available
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cocaine esterase
Reactions: Not Available
Gene Name: CES2
Uniprot ID: O00748 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 2
Reactions: Not Available
Gene Name: SOAT2
Uniprot ID: O75908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 1
Reactions: Not Available
Gene Name: SOAT1
Uniprot ID: P35610 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 gamma
Reactions: Not Available
Gene Name: PLA2G4C
Uniprot ID: Q9UP65 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile acid-CoA:amino acid N-acyltransferase
Reactions: Not Available
Gene Name: BAAT
Uniprot ID: Q14032 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-2
Reactions: Not Available
Gene Name: ACYP2
Uniprot ID: P14621 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-1
Reactions: Not Available
Gene Name: ACYP1
Uniprot ID: P07311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Long-chain fatty acid transport protein 1
Reactions: Not Available
Gene Name: SLC27A1
Uniprot ID: Q6PCB7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA