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Human Metabolome Database Version 2.5

 

Showing metabocard for 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA (HMDB06895)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2008-08-14 19:18:11
Update Date 2009-05-05 21:01:16
Accession Number HMDB06895
Secondary Accession Numbers Not Available
Common Name 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA
Description 3alpha,7alpha-Dihydroxy-5beta-cholest-24-enoyl-CoA is an intermediate involved in bile acid synthesis, specifically in the synthesis of chenodeoxyglycocholate. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135)
Synonyms
  1. 3alpha,7alpha-Dihydroxy-5beta-cholest-24-enoyl-Coenzyme A
  2. 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA
  3. 3a,7a-Dihydroxy-5b-cholest-24-enoyl-Coenzyme A
  4. 3alpha,7alpha-Dihydroxy-5beta-cholest-24-enoyl-CoA
Chemical IUPAC Name S-[2-[3-[[4-[[[(2R,3S,4R, 5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy- hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3, 3-dimethylbutanoyl]amino]propanoylamino]ethyl] (E)-6-[(3R,5S,7R,10S,13R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9, 11,12,14,15,16, 17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2- enethioate
Chemical Formula C48H78N7O19P3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Coenzyme A Derivatives
Sub Class
  • Long chain acyl CoAs
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • primary amine
  • primary aromatic amine
  • secondary carboxylic acid amide
  • thiocarboxylic acid ester
  • phosphoric acid ester
  • alkene
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 1182.155
Monoisotopic Molecular Weight 1181.428589
Isomeric SMILES CC(CCC=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=C1N=CN=C2N)C1CCC2C3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C
Canonical SMILES CC(CCC=C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C05447 Link Image
BioCyc ID Not Available
BiGG ID 45830 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB06895 Link Image
Metagene Link HMDB06895 Link Image
METLIN ID Not Available
PubChem Compound 5280796 Link Image
PubChem Substance 7809 Link Image
ChEBI ID 27393 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/C48H78N7O19P3S/c1-26(30-10-11-31-36-32(13-16-48(30,31)6)47(5)15-12-29(56)20-28(47)21-33(36)57)8-7-9-27(2)45(62)78-19-18-50-35(58)14-17-51-43(61)40(60)46(3,4)23-71-77(68,69)74-76(66,67)70-22-34-39(73-75(63,64)65)38(59)44(72-34)55-25-54-37-41(49)52-24-53-42(37)55/h9,24-26,28-34,36,38-40,44,56-57,59-60H,7-8,10-23H2,1-6H3,(H,50,58)(H,51,61)(H,66,67)(H,68,69)(H2,49,52,53)(H2,63,64,65)/b27-9+/t26?,28-,29+,30?,31?,32?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.205 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -4
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.88 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References Not Available
Metabolic Enzymes
  1. Isobutyryl-CoA dehydrogenase, mitochondrial precursor
Enzyme 1 [top]
Enzyme 1 ID 10872
Enzyme 1 Name Isobutyryl-CoA dehydrogenase, mitochondrial precursor
Enzyme 1 Synonyms
  1. Acyl-CoA dehydrogenase family member 8
  2. ACAD-8
  3. Activator-recruited cofactor 42 kDa component
  4. ARC42
Enzyme 1 Gene Name ACAD8
Enzyme 1 Protein Sequence >Isobutyryl-CoA dehydrogenase, mitochondrial precursor 
MLWSGCRRFGARLGCLPGGLRVLVQTGHRSLTSCIDPSMGLNEEQKEFQKVAFDFAAREM
APNMAEWDQKELFPVDVMRKAAQLGFGGVYIQTDVGGSGLSRLDTSVIFEALATGCTSTT
AYISIHNMCAWMIDSFGNEEQRHKFCPPLCTMEKFASYCLTEPGSGSDAASLLTSAKKQG
DHYILNGSKAFISGAGESDIYVVMCRTGGPGPKGISCIVVEKGTPGLSFGKKEKKVGWNS
QPTRAVIFEDCAVPVANRIGSEGQGFLIAVRGLNGGRINIASCSLGAAHASVILTRDHLN
VRKQFGEPLASNQYLQFTLADMATRLVAARLMVRNAAVALQEERKDAVALCSMAKLFATD
ECFAICNQALQMHGGYGYLKDYAVQQYVRDSRVHQILEGSNEVMRILISRSLLQE
Enzyme 1 Number of Residues 415
Enzyme 1 Molecular Weight 45070
Enzyme 1 Theoretical pI Not Available
Enzyme 1 GO Classification
Function
  • acyl-CoA dehydrogenase activity
  • catalytic activity
  • oxidoreductase activity
  • oxidoreductase activity, acting on the CH-CH group of donors
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Lipid transport and metabolism
Enzyme 1 Specific Function Has very high activity toward isobutyryl-CoA. Is an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Plays a role in transcriptional coactivation within the ARC complex
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • Flavin adenine dinucleotide oxidized + Propanoyl-CoA --> Flavin adenine dinucleotide reduced + Propenoyl-CoA
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 6465955 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q9UKU7 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name ACAD8_HUMAN Link Image
Enzyme 1 PDB ID 1RX0 Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AF126245 Link Image
Enzyme 1 GeneCard ID Not Available
Enzyme 1 GenAtlas ID ACAD8 Link Image
Enzyme 1 HGNC ID HGNC:87 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Telford EA, Moynihan LM, Markham AF, Lench NJ: Isolation and characterisation of a cDNA encoding the precursor for a novel member of the acyl-CoA dehydrogenase gene family. Biochim Biophys Acta. 1999 Sep 3;1446(3):371-6. [PubMed Link Image]
  2. Andresen BS, Christensen E, Corydon TJ, Bross P, Pilgaard B, Wanders RJ, Ruiter JP, Simonsen H, Winter V, Knudsen I, Schroeder LD, Gregersen N, Skovby F: Isolated 2-methylbutyrylglycinuria caused by short/branched-chain acyl-CoA dehydrogenase deficiency: identification of a new enzyme defect, resolution of its molecular basis, and evidence for distinct acyl-CoA dehydrogenases in isoleucine and valine metabolism. Am J Hum Genet. 2000 Nov;67(5):1095-103. Epub 2000 Sep 29. [PubMed Link Image]
  3. Naar AM, Beaurang PA, Zhou S, Abraham S, Solomon W, Tjian R: Composite co-activator ARC mediates chromatin-directed transcriptional activation. Nature. 1999 Apr 29;398(6730):828-32. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available