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Human Metabolome Database Version 3.5

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Showing metabocard for 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA (HMDB12456)

Record Information
Version 3.5
Creation Date 2009-07-13 07:21:08 -0600
Update Date 2013-02-08 17:29:10 -0700
HMDB ID HMDB12456
Secondary Accession Numbers None
Metabolite Identification
Common Name 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA
Description 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is found in the primary bile acid biosynthesis pathway. 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is created from 3 alpha,7 alpha-Dihydroxy-5beta-cholest-24-enoyl-CoA through the action of HSD17B4 (EC4.2.1.107). 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is then converted to 3 alpha,7 alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA by HSD17B4 (EC1.1.1.35).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
    Chemical Formula C48H80N7O20P3S
    Average Molecular Weight 1200.17
    Monoisotopic Molecular Weight 1199.439168261
    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]-3-hydroxy-2-methylheptanoyl}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]-3-hydroxy-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy
    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/C48H80N7O20P3S/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/h23-34,36,38-40,44,56-58,60-61H,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?,32?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
    InChI Key SZBMUAIJWNJARR-ATZLTZGYSA-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
    • 24 Hydroxy 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
    • Glycosyl Compound
    • Hydroxy Bile Acid, Alcohol, Or Derivative
    • Imidazole
    • Imidazopyrimidine
    • 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
    • Trihydroxy Bile Acid, Alcohol, Or Derivative
    • 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 0.71 g/L ALOGPS
    LogP 1.24 ALOGPS
    LogP -2.8 ChemAxon
    LogS -3.23 ALOGPS
    pKa (strongest acidic) 0.83 ChemAxon
    pKa (strongest basic) 4.95 ChemAxon
    Hydrogen Acceptor Count 20 ChemAxon
    Hydrogen Donor Count 12 ChemAxon
    Polar Surface Area 424.32 A2 ChemAxon
    Rotatable Bond Count 26 ChemAxon
    Refractivity 284.13 ChemAxon
    Polarizability 119.5 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
    Name SMPDB Link KEGG Link
    Bile Acid Biosynthesis SMP00035 map00120 Link_out
    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 FDB029072
    KNApSAcK ID Not Available
    Chemspider ID 389554 Link_out
    KEGG Compound ID C05448 Link_out
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB12456 Link_out
    Metagene Link HMDB12456 Link_out
    METLIN ID Not Available
    PubChem Compound 440675 Link_out
    PDB ID Not Available
    ChEBI ID 27403 Link_out
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References Not Available