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Record Information
Version	2.0
Creation Date	2012-05-31 13:55:51 -0600
Update Date	2015-06-03 15:54:15 -0600
Secondary Accession Numbers	ECMDB02159
Identification
Name:	3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
Description	Trans-octadec-2-enoyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x73ca8c08> Close
Synonyms:	3-a,7-a-Dihydroxy-5-b-cholestanoyl-CoA 3-a,7-a-Dihydroxy-5-b-cholestanoyl-coenzyme A 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-CoA 3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-Coenzyme A 3-α,7-α-Dihydroxy-5-β-cholestanoyl-CoA 3-α,7-α-Dihydroxy-5-β-cholestanoyl-coenzyme A 3a,7a-Dihydroxy-5b-cholestanoyl-CoA 3a,7a-Dihydroxy-5b-cholestanoyl-coenzyme A 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-Coenzyme A 3α,7α-Dihydroxy-5β-cholestanoyl-CoA 3α,7α-Dihydroxy-5β-cholestanoyl-coenzyme A DHCA
Chemical Formula:	C48H80N7O19P3S
Weight:	Average: 1184.171 Monoisotopic: 1183.444253639
InChI Key:	SBYLHTNKEWSLBA-CPRJDYHCSA-N
InChI:	InChI=1S/C48H80N7O19P3S/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/h24-34,36,38-40,44,56-57,59-60H,7-23H2,1-6H3,(H,50,58)(H,51,61)(H,66,67)(H,68,69)(H2,49,52,53)(H2,63,64,65)/t26?,27?,28-,29+,30?,31?,32?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
CAS number:	2461-62-3
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-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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
SMILES:	[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCCC(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=C(N)N=CN=C12
Chemical Taxonomy
Description	belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	2,3,4-saturated fatty acyl CoAs
Alternative Parents	Medium-chain fatty acyl CoAs Coenzyme A and derivatives Steroidal glycosides Purine ribonucleoside diphosphates Dihydroxy bile acids, alcohols and derivatives 3-alpha-hydroxysteroids 7-hydroxysteroids Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Aminopyrimidines and derivatives N-substituted imidazoles N-acyl amines Imidolactams Tetrahydrofurans Heteroaromatic compounds Thioesters Carbothioic S-esters Secondary alcohols Cyclic alcohols and derivatives Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Sulfenyl compounds Organopnictogen compounds Hydrocarbon derivatives Organic oxides Carbonyl compounds Primary amines
Substituents	Coenzyme a or derivatives Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Steroidal glycoside Dihydroxy bile acid, alcohol, or derivatives Hydroxy bile acid, alcohol, or derivatives Cholane-skeleton Bile acid, alcohol, or derivatives 3-hydroxysteroid Hydroxysteroid 3-alpha-hydroxysteroid 7-hydroxysteroid Steroid Ribonucleoside 3'-phosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound Organic pyrophosphate 6-aminopurine Pentose monosaccharide Monosaccharide phosphate Purine Imidazopyrimidine Monoalkyl phosphate Aminopyrimidine Pyrimidine Monosaccharide N-acyl-amine Phosphoric acid ester Fatty amide N-substituted imidazole Imidolactam Organic phosphoric acid derivative Alkyl phosphate Azole Tetrahydrofuran Cyclic alcohol Imidazole Heteroaromatic compound Amino acid or derivatives Carbothioic s-ester Carboxamide group Thiocarboxylic acid ester Secondary carboxylic acid amide Secondary alcohol Thiocarboxylic acid or derivatives Oxacycle Sulfenyl compound Azacycle Carboxylic acid derivative Organoheterocyclic compound Primary amine Alcohol Carbonyl group Organic oxygen compound Organosulfur compound Organooxygen compound Organopnictogen compound Amine Organic nitrogen compound Organonitrogen compound Hydrocarbon derivative Organic oxide Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.37 g/L ALOGPS logP 1.86 ALOGPS logP -1.6 ChemAxon logS -3.5 ALOGPS pKa (Strongest Acidic) 0.83 ChemAxon pKa (Strongest Basic) 4.95 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 11 ChemAxon Polar Surface Area 404.09 Ų ChemAxon Rotatable Bond Count 26 ChemAxon Refractivity 282.61 m³·mol⁻¹ ChemAxon Polarizability 117.46 ų ChemAxon Number of Rings 7 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Propionyl-CoA + Chenodeoxycholoyl-CoA <> Coenzyme A + 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-1900112000-0c75e0a93454d43ab753 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900314000-ee39276da14ef1ec86d2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1900000010-5f6513051536bb79e578 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00lr-2901332400-00267947c2aa67bae2f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-3900111010-35ffb32be4339618cff9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-125c30cd4205b3d5be3d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0159-0900000000-eb50c2a058862834d250 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0159-0900102622-13f5492940fca24737d0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004i-0000119000-c789136e01e3fc6660ea View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-0900000000-787baca3a444ef57d1b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-2900301100-c831b98264288f5ecac5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0170-6605603900-a71bad576505bfdacb19 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Keseler, I. M., Collado-Vides, J., Gama-Castro, S., Ingraham, J., Paley, S., Paulsen, I. T., Peralta-Gil, M., Karp, P. D. (2005). "EcoCyc: a comprehensive database resource for Escherichia coli." Nucleic Acids Res 33:D334-D337. Pubmed: 15608210 Prydz K, Kase BF, Bjorkhem I, Pedersen JI: Subcellular localization of 3 alpha, 7 alpha-dihydroxy- and 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoyl-coenzyme A ligase(s) in rat liver. J Lipid Res. 1988 Aug;29(8):997-1004. Pubmed: 3183523
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15494 HMDB ID HMDB02159 Pubchem Compound ID 440420 Kegg ID C04644 ChemSpider ID 389367 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes