ChemFOnt: Showing chemical card for Choloyl-CoA (CFc000001062)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:37 UTC

Chemfont ID

CFc000001062

Molecule Identification

Common Name

Choloyl-CoA

Definition

Choloyl-CoA is an intermediate metabolite in the Bile acid biosynthesis (KEGG). The conjugation of bile acids to glycine and taurine for excretion into bile occurs via a reaction catalyzed by the enzyme Bile acid-CoA:amino acid N-acyltransferase (BACAT) catalyzes.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-alpha-12-alpha-Dihydroxy-3-oxo-5-beta-cholyl-CoA	HMDB
Choloyl-coenzyme A	HMDB
Cholyl-CoA	HMDB
Cholyl-coenzyme A	HMDB

Chemical Formula

C₄₅H₇₄N₇O₂₀P₃S

Average Molecular Weight

1158.09

Monoisotopic Molecular Weight

1157.392218069

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({4-[(1S,5R,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({4-[(1S,5R,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

None

SMILES

[H][C@@]12CCC(C(C)CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)CC2C[C@H](O)CCC12C

InChI Identifier

InChI=1S/C45H74N7O20P3S/c1-23(26-7-8-27-34-28(18-31(55)45(26,27)5)44(4)12-10-25(53)16-24(44)17-29(34)54)6-9-33(57)76-15-14-47-32(56)11-13-48-41(60)38(59)43(2,3)20-69-75(66,67)72-74(64,65)68-19-30-37(71-73(61,62)63)36(58)42(70-30)52-22-51-35-39(46)49-21-50-40(35)52/h21-31,34,36-38,42,53-55,58-59H,6-20H2,1-5H3,(H,47,56)(H,48,60)(H,64,65)(H,66,67)(H2,46,49,50)(H2,61,62,63)/t23?,24?,25-,26?,27+,28+,29-,30-,31+,34?,36-,37-,38?,42-,44?,45?/m1/s1

InChI Key

ZKWNOTQHFKYUNU-TVKZAFKCSA-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
Steroidal glycoside
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Cholane-skeleton
Bile acid, alcohol, or derivatives
7-hydroxysteroid
12-hydroxysteroid
3-alpha-hydroxysteroid
3-hydroxysteroid
Hydroxysteroid
Steroid
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Pyrimidine
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Cyclic alcohol
Azole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carbothioic s-ester
Amino acid or derivatives
Thiocarboxylic acid ester
Sulfenyl compound
Organoheterocyclic compound
Thiocarboxylic acid or derivatives
Polyol
Azacycle
Oxacycle
Carboxylic acid derivative
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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: HMDB0001374)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001374)

Source

Endogenous

Endogenous (HMDB: HMDB0001374)

Animal

Animal (HMDB: HMDB0001374)

Exogenous

Food

Food (HMDB: HMDB0001374)

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: HMDB0001374)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001374)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0001374)
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: HMDB0001374)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0001374)

Cellular process

Cell signaling (HMDB: HMDB0001374)

Biochemical process

Lipid transport (HMDB: HMDB0001374)

Role

Biological role

Energy source (HMDB: HMDB0001374)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001374)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	0.56	ALOGPS
logP	-4.3	ChemAxon
logS	-2.9	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	24	ChemAxon
Refractivity	270.35 m³·mol⁻¹	ChemAxon
Polarizability	114.43 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