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3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA (FDB024143)

Record Information
Version1.0
Creation date2011-09-21 00:40:33 UTC
Update date2015-07-21 06:58:00 UTC
Primary IDFDB024143
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA
Description3alpha,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, 16037564, 12576301, 11907135) [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.8 g/LALOGPS
logP1.48ALOGPS
logP-2.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity283.31 m³·mol⁻¹ChemAxon
Polarizability118.54 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H78N7O20P3S
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[8.7.0.0²,⁷.0¹¹,¹⁵]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
InChI IdentifierInChI=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 KeyQWTJBRPOHKIMDT-XWFLEUKDSA-N
Isomeric 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
Average Molecular Weight1198.154
Monoisotopic Molecular Weight1197.423518197
Classification
Description Belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Steroidal glycoside
  • Dihydroxy bile acid, alcohol, or derivatives
  • 24-oxosteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Steroid
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Beta amino acid or derivatives
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • 1,3-dicarbonyl compound
  • Phosphoric acid ester
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Cyclic alcohol
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Ketone
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Oxacycle
  • Primary amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organosulfur compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900011000-ee37845dcec7f534b9492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900224000-2ac4acd3a7a592025c9b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900011000-eba9ad2646b815c5653d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-2900431400-c3b2261f65b65612d0a42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900211010-7af67f1bdda03ff5f92b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-274586d0a37c06be3a7a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0910000000-5227de7e037e6fc18dab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0900000011-0b2317c4d491e46a73772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000019000-3349b28b210614d4616c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b3d487f70b4ec1efc5b12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1900401100-47eeb25caf0cd319c8252021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ra-7604804900-b37dd229af4ceda615572021-09-22View Spectrum
NMRNot Available
ChemSpider ID389555
ChEMBL IDNot Available
KEGG Compound IDC05449
Pubchem Compound ID440676
Pubchem Substance IDNot Available
ChEBI ID28533
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06896
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Non-specific lipid-transfer proteinSCP2P22307
3-ketoacyl-CoA thiolase, peroxisomalACAA1P09110
Trifunctional enzyme subunit beta, mitochondrialHADHBP55084
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference