ChemFOnt: Showing chemical card for 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA (CFc000007981)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:34 UTC

Chemfont ID

CFc000007981

Molecule Identification

Common Name

3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3 a,7 a,24-Trihydroxy-5b-cholestanoyl-CoA	Generator
3 Α,7 α,24-trihydroxy-5β-cholestanoyl-CoA	Generator
3alpha,7alpha,24-Trihydroxy-5beta-cholestan-26-oyl-coenzyme A	ChEBI
3alpha,7alpha,24-Trihydroxy-5beta-cholestanoyl-CoA	ChEBI
(24R,25R)-3alpha,7alpha,24-Trihydroxy-5beta-cholestan-26-oyl-CoA	KEGG
3a,7a,24-Trihydroxy-5b-cholestan-26-oyl-coenzyme A	Generator
3Α,7α,24-trihydroxy-5β-cholestan-26-oyl-coenzyme A	Generator
3a,7a,24-Trihydroxy-5b-cholestanoyl-CoA	Generator
3Α,7α,24-trihydroxy-5β-cholestanoyl-CoA	Generator
(24R,25R)-3a,7a,24-Trihydroxy-5b-cholestan-26-oyl-CoA	Generator
(24R,25R)-3Α,7α,24-trihydroxy-5β-cholestan-26-oyl-CoA	Generator

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[8.7.0.0²,⁷.0¹¹,¹⁵]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 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]-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]oxyphosphonic acid

CAS Registry Number

None

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

Description

Belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-hydroxyacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Steroidal glycoside
Trihydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
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
Monosaccharide phosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Pyrimidine
Fatty amide
Monosaccharide
N-acyl-amine
Phosphoric acid ester
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
Secondary alcohol
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Oxacycle
Azacycle
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Carboxylic acid derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Primary amine
Alcohol
Organosulfur compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012456)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012456)

Source

Endogenous

Endogenous (HMDB: HMDB0012456)

Animal

Animal (HMDB: HMDB0012456)

Exogenous

Food

Food (HMDB: HMDB0012456)

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: HMDB0012456)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012456)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0012456)
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: HMDB0012456)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0012456)

Cellular process

Cell signaling (HMDB: HMDB0012456)

Biochemical process

Lipid transport (HMDB: HMDB0012456)

Role

Biological role

Energy source (HMDB: HMDB0012456)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012456)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	1.24	ALOGPS
logP	-2.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	424.32 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	284.13 m³·mol⁻¹	ChemAxon
Polarizability	119.5 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

HMDB0012456

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029072

KNApSAcK ID

Not Available

Chemspider ID

26333133

KEGG Compound ID

C05448

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440675

PDB ID

Not Available

ChEBI ID

27403

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA (CFc000007981)

MOL for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

3D MOL for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

3D SDF for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

3D-SDF for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

PDB for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

3D PDB for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

SMILES for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

INCHI for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

Structure for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)

3D Structure for CFc000007981 (3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA)