ChemFOnt: Showing chemical card for Malonyl-CoA semialdehyde (CFc000001457)

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

CFc000001457

Molecule Identification

Common Name

Malonyl-CoA semialdehyde

Definition

Malonyl-CoA semialdehyde is involved in the propanoate metabolism pathway. Malonyl-CoA semialdehyde can be reversibly produced from malonyl-CoA and 3-hydroxy-propionyl-CoA. Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. Studies of these pathways in cultured cells from a patient with mitochondrial malonyl-CoA decarboxylase deficiency indicate that malonic semialdehyde is directly converted into acetyl-CoA in man. (PMID: 6418146 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Thiomalonaldehydic acid S-ester with coenzyme A	HMDB
3-Oxopropionyl-CoA	HMDB
3-Oxopropionyl-coenzyme A	HMDB
Malonylsemialdehyde coenzyme A	HMDB
Malonylsemialdehyde-CoA	HMDB
Malonylsemialdehyde-coenzyme A	HMDB
S-(3-Oxopropanoate	HMDB
S-(3-Oxopropanoate)CoA	HMDB
S-(3-Oxopropanoate)coenzyme A	HMDB
S-(3-Oxopropanoic acid	HMDB

Chemical Formula

C₂₄H₃₈N₇O₁₈P₃S

Average Molecular Weight

837.581

Monoisotopic Molecular Weight

837.120687673

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-[(3-oxopropanoyl)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-[(3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

6244-93-5

SMILES

CC(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)C(O)C(=O)NCCC(=O)NCCSC(=O)CC=O

InChI Identifier

InChI=1S/C24H38N7O18P3S/c1-24(2,19(36)22(37)27-5-3-14(33)26-6-8-53-15(34)4-7-32)10-46-52(43,44)49-51(41,42)45-9-13-18(48-50(38,39)40)17(35)23(47-13)31-12-30-16-20(25)28-11-29-21(16)31/h7,11-13,17-19,23,35-36H,3-6,8-10H2,1-2H3,(H,26,33)(H,27,37)(H,41,42)(H,43,44)(H2,25,28,29)(H2,38,39,40)/t13-,17-,18-,19?,23-/m1/s1

InChI Key

NMEYBPUHJHMRHU-UXYNFSPESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Pentose phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Monosaccharide phosphate
Organic pyrophosphate
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Fatty amide
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Imidolactam
Alkyl phosphate
Phosphoric acid ester
1,3-dicarbonyl compound
Pyrimidine
Tetrahydrofuran
Azole
Heteroaromatic compound
Imidazole
Alpha-hydrogen aldehyde
Carbothioic s-ester
Amino acid or derivatives
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Carboxamide group
Secondary alcohol
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Organosulfur compound
Aldehyde
Carbonyl group
Primary amine
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organ

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0002170)
Skeletal muscle (HMDB: HMDB0002170)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002170)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002170)

Source

Endogenous

Endogenous (HMDB: HMDB0002170)

Animal

Animal (HMDB: HMDB0002170)

Exogenous

Food

Food (HMDB: HMDB0002170)

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: HMDB0002170)

Process

Role

Biological role

Energy source (HMDB: HMDB0002170)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002170)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.96 g/L	ALOGPS
logP	-0.34	ALOGPS
logP	-7.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	177.63 m³·mol⁻¹	ChemAxon
Polarizability	72.58 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

HMDB0002170

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022882

KNApSAcK ID

Not Available

Chemspider ID

389702

KEGG Compound ID

C05989

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6523

PubChem Compound

440865

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malonyl-CoA semialdehyde (CFc000001457)

MOL for CFc000001457 (Malonyl-CoA semialdehyde)

3D MOL for CFc000001457 (Malonyl-CoA semialdehyde)

3D SDF for CFc000001457 (Malonyl-CoA semialdehyde)

3D-SDF for CFc000001457 (Malonyl-CoA semialdehyde)

PDB for CFc000001457 (Malonyl-CoA semialdehyde)

3D PDB for CFc000001457 (Malonyl-CoA semialdehyde)

SMILES for CFc000001457 (Malonyl-CoA semialdehyde)

INCHI for CFc000001457 (Malonyl-CoA semialdehyde)

Structure for CFc000001457 (Malonyl-CoA semialdehyde)

3D Structure for CFc000001457 (Malonyl-CoA semialdehyde)