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Human Metabolome Database Version 3.5

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Showing metabocard for 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA (HMDB06896)

Record Information
Version 3.5
Creation Date 2008-08-14 12:27:14 -0600
Update Date 2013-02-08 17:15:30 -0700
HMDB ID HMDB06896
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA
Description 3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA is an intermediate involved in the synthesis of Chenodeoxyglycocholoyl-CoA, which is is a coenzyme A derivative of chenodeoxyglycocholate. It is involved in bile acid synthesis and is the second-to-last component in the synthesis of chenodeoxyglycocholate. 3a,7a-dihydroxy-5b-24-oxocholestanoyl-CoA is synthesized from 3a,7a,24-trihydroxy-5b-cholestanoyl-CoA and then transformed via acetyl-CoA acyltransferase to chenodeoxyglycocholoyl-CoA and then finally to chenodeoxyglycocholate. Chenodeoxyglycocholate is a glycine conjugated bile acid. 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 Link_out, 16037564 Link_out, 12576301 Link_out, 11907135 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA
  2. 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-Coenzyme A
  3. 3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA
  4. 3alpha,7alpha-Dihydroxy-5beta-24-oxocholestanoyl-Coenzyme A
Chemical Formula C48H78N7O20P3S
Average Molecular Weight 1198.154
Monoisotopic Molecular Weight 1197.423518197
IUPAC Name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methyl-3-oxoheptanoyl}sulfanyl)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-{[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methyl-3-oxoheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hyd
CAS Registry Number Not Available
SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(=O)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
InChI Identifier InChI=1S/C48H78N7O20P3S/c1-25(29-8-9-30-36-31(12-15-48(29,30)6)47(5)14-11-28(56)19-27(47)20-33(36)58)7-10-32(57)26(2)45(63)79-18-17-50-35(59)13-16-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-34-39(74-76(64,65)66)38(60)44(73-34)55-24-54-37-41(49)52-23-53-42(37)55/h23-31,33-34,36,38-40,44,56,58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25?,26?,27-,28+,29?,30?,31?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
InChI Key QWTJBRPOHKIMDT-XWFLEUKDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • 3-Oxo-acyl CoAs
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • 24 Keto Steroid
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Aminopyrimidine
  • Bicyclohexane
  • Bile Acid, Alcohol, Or Derivative
  • Carboxamide Group
  • Carboxylic Thioester
  • Cholesterol
  • Coenzyme A
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Dihydroxy Bile Acid, Alcohol, Or Derivative
  • Glycosyl Compound
  • Hydroxy Bile Acid, Alcohol, Or Derivative
  • Imidazole
  • Imidazopyrimidine
  • Ketone
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Polycyclic Triterpene
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Steroid
  • Terpene Glycoside
  • Thiocarboxylic Acid Ester
  • Triterpene
  • Triterpene Glycoside
Direct Parent Steroidal Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 0.8 g/L ALOGPS
LogP 1.48 ALOGPS
LogP -2.3 ChemAxon
LogS -3.17 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 20 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 421.16 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 283.31 ChemAxon
Polarizability 118.54 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024143
KNApSAcK ID Not Available
Chemspider ID 389555 Link_out
KEGG Compound ID C05449 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06896 Link_out
Metagene Link HMDB06896 Link_out
METLIN ID Not Available
PubChem Compound 440676 Link_out
PDB ID Not Available
ChEBI ID 28533 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions:
  • acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA [RN:R00391]
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions:
  • acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA [RN:R00391]
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA