ChemFOnt: Showing chemical card for L-Citramalyl-CoA (CFc000002727)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:40 UTC

Chemfont ID

CFc000002727

Molecule Identification

Common Name

L-Citramalyl-CoA

Definition

L-Citramalyl-CoA is an intermediate in C5-Branched dibasic acid metabolism. L-Citramalyl-CoA is the 3rd to last step in the synthesis of (R)-Acetoin and is converted from L-Citramalate via the enzyme citramalate CoA-transferase (EC 2.8.3.7). It is then converted to Pyruvate via the enzyme citramalate-CoA lyase (EC 4.1.3.25).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S)-Citramalyl-CoA	HMDB
(3S)-Citramalyl-coenzyme A	HMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-hydroxy-2-methyl-4-oxobutanoate	Generator, HMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-2-methyl-4-oxobutanoate	Generator, HMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-2-methyl-4-oxobutanoic acid	Generator, HMDB

Chemical Formula

C₂₆H₄₂N₇O₂₀P₃S

Average Molecular Weight

897.633

Monoisotopic Molecular Weight

897.141817045

IUPAC Name

(2S)-4-[(2-{3-[(2R)-3-[({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-hydroxy-2-methyl-4-oxobutanoic acid

Traditional Name

(2S)-4-[(2-{3-[(2R)-3-{[({[(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-hydroxy-2-methyl-4-oxobutanoic acid

CAS Registry Number

None

SMILES

[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C[C@](C)(O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C26H42N7O20P3S/c1-25(2,19(37)22(38)29-5-4-14(34)28-6-7-57-15(35)8-26(3,41)24(39)40)10-50-56(47,48)53-55(45,46)49-9-13-18(52-54(42,43)44)17(36)23(51-13)33-12-32-16-20(27)30-11-31-21(16)33/h11-13,17-19,23,36-37,41H,4-10H2,1-3H3,(H,28,34)(H,29,38)(H,39,40)(H,45,46)(H,47,48)(H2,27,30,31)(H2,42,43,44)/t13-,17+,18?,19+,23-,26+/m1/s1

InChI Key

XYGOWHUIVNMEIA-KKAINBEZSA-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
Pentose phosphate
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Hydroxy fatty acid
Monoalkyl phosphate
Thia fatty acid
Imidolactam
Fatty amide
Alpha-hydroxy acid
Hydroxy acid
Alkyl phosphate
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Tertiary alcohol
Imidazole
Azole
Heteroaromatic compound
Tetrahydrofuran
Carbothioic s-ester
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboxamide group
Thiocarboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Thiocarboxylic acid or derivatives
Carboxylic acid
Oxacycle
Organopnictogen compound
Organic nitrogen compound
Alcohol
Amine
Carbonyl group
Primary amine
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006345)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006345)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006345)

Source

Endogenous

Endogenous (HMDB: HMDB0006345)

Animal

Animal (HMDB: HMDB0006345)

Exogenous

Food

Food (HMDB: HMDB0006345)

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: HMDB0006345)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006345)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006345)

Lipid metabolism pathway (HMDB: HMDB0006345)

Cellular process

Cell signaling (HMDB: HMDB0006345)

Biochemical process

Lipid transport (HMDB: HMDB0006345)

Role

Biological role

Energy source (HMDB: HMDB0006345)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006345)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.2 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-7.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	421.16 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	189.15 m³·mol⁻¹	ChemAxon
Polarizability	78.31 Å³	ChemAxon
Number of Rings	3	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

HMDB0006345

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023897

KNApSAcK ID

Not Available

Chemspider ID

35015991

KEGG Compound ID

C01011

BioCyc ID

Not Available

BiGG ID

36606

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477827

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for L-Citramalyl-CoA (CFc000002727)

MOL for CFc000002727 (L-Citramalyl-CoA)

3D MOL for CFc000002727 (L-Citramalyl-CoA)

3D SDF for CFc000002727 (L-Citramalyl-CoA)

3D-SDF for CFc000002727 (L-Citramalyl-CoA)

PDB for CFc000002727 (L-Citramalyl-CoA)

3D PDB for CFc000002727 (L-Citramalyl-CoA)

SMILES for CFc000002727 (L-Citramalyl-CoA)

INCHI for CFc000002727 (L-Citramalyl-CoA)

Structure for CFc000002727 (L-Citramalyl-CoA)

3D Structure for CFc000002727 (L-Citramalyl-CoA)