ChemFOnt: Showing chemical card for 3a,7a-Dihydroxy-5b-cholestanoyl-CoA (CFc000001450)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:05 UTC

Chemfont ID

CFc000001450

Molecule Identification

Common Name

3a,7a-Dihydroxy-5b-cholestanoyl-CoA

Definition

First activated by a fatty acyl-CoA ligase activity, can then be converted to chenodeoxycholic acid by peroxisome rich fractions from rat and human liver (J Lipid Res. 1988 Aug;29(8):997-1004, PMID 3183523 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-CoA	HMDB
3-alpha,7-alpha-Dihydroxy-5-beta-cholestanoyl-coenzyme A	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-coenzyme A	HMDB
DHCA	HMDB

Chemical Formula

C₄₈H₈₀N₇O₁₉P₃S

Average Molecular Weight

1184.171

Monoisotopic Molecular Weight

1183.444253639

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 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

CAS Registry Number

2461-62-3

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

InChI Identifier

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

InChI Key

SBYLHTNKEWSLBA-CPRJDYHCSA-N

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

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0002159)
Peroxisome (HMDB: HMDB0002159)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002159)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002159)

Source

Endogenous

Endogenous (HMDB: HMDB0002159)

Animal

Animal (HMDB: HMDB0002159)

Exogenous

Food

Food (HMDB: HMDB0002159)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002159)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002159)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0002159)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002159)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0002159)

Cellular process

Cell signaling (HMDB: HMDB0002159)

Biochemical process

Lipid transport (HMDB: HMDB0002159)

Role

Biological role

Energy source (HMDB: HMDB0002159)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002159)

Physical Properties

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 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	282.61 m³·mol⁻¹	ChemAxon
Polarizability	117.46 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0002159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022875

KNApSAcK ID

Not Available

Chemspider ID

24850079

KEGG Compound ID

C04644

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440420

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3a,7a-Dihydroxy-5b-cholestanoyl-CoA (CFc000001450)

MOL for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

3D MOL for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

3D SDF for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

3D-SDF for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

PDB for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

3D PDB for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

SMILES for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

INCHI for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

Structure for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)

3D Structure for CFc000001450 (3a,7a-Dihydroxy-5b-cholestanoyl-CoA)