Bovine Metabolome Database: Showing metabocard for Malonyl-CoA (BMDB0001175)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:42:02 UTC

Update Date

2020-05-21 16:29:02 UTC

BMDB ID

BMDB0001175

Secondary Accession Numbers

BMDB01175

Metabolite Identification

Common Name

Malonyl-CoA

Description

Malonyl-CoA, also known as malonyl CoA or CoA, malonyl, 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. Malonyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Malonyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Malonyl-CoA can be biosynthesized from acetyl-CoA through its interaction with the enzyme acetyl-CoA carboxylase 1. In addition, Malonyl-CoA can be converted into malonic acid and coenzyme A through the action of the enzyme fatty acid synthase. malonyl/acetyl transferase domain. In cattle, malonyl-CoA is involved in the metabolic pathway called fatty acid biosynthesis pathway. Malonyl-CoA is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Malonyl CoA	HMDB
Malonyl coenzyme A	HMDB
Malonyl-coenzyme A	HMDB
Omega-carboxyacyl-CoA	HMDB
Omega-carboxyacyl-coenzyme A	HMDB
S-(Hydrogen malonyl)coenzyme A	HMDB
S-(Hydrogen propanedioate	HMDB
S-(Hydrogen propanedioate) CoA	HMDB
S-(Hydrogen propanedioate) coenzyme A	HMDB
S-(Hydrogen propanedioic acid	HMDB
a, Malonyl coenzyme	HMDB
CoA, Malonyl	HMDB
coenzyme A, Malonyl	HMDB

Chemical Formula

C₂₄H₃₈N₇O₁₉P₃S

Average Molecular Weight

853.58

Monoisotopic Molecular Weight

853.115602295

IUPAC Name

3-{[2-(3-{3-[({[({[(2R,3S,4R,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}-3-oxopropanoic acid

Traditional Name

3-({2-[3-(3-{[({[(2R,3S,4R,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)-3-oxopropanoic acid

CAS Registry Number

524-14-1

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)=O

InChI Identifier

InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1

InChI Key

LTYOQGRJFJAKNA-VFLPNFFSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-oxo monocarboxylic acid (CHEBI:16256 )
Oxo fatty acids (LMFA01060193 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane
Mitochondria
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.5	ALOGPS
logP	-6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.2	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	400.93 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	178.55 m³·mol⁻¹	ChemAxon
Polarizability	74.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Adipose Tissue
Fibroblasts
Liver
Pancreas
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyruvate Metabolism		Not Available
Propanoate Metabolism		Not Available
Fatty Acid Biosynthesis		Not Available
LPS and Citrate Signaling and Inflammation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001175

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15531

References

Synthesis Reference

Hulsmann, W. C. Synthesis of malonyl coenzyme A from acetyl coenzyme A and oxalosuccinate in mitochondria. Biochimica et Biophysica Acta (1963), 77(3), 502-3.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetyl-CoA carboxylase 1

General function:: Lipid transport and metabolism
Specific function:: Cytosolic enzyme that catalyzes the carboxylation of acetyl-CoA to malonyl-CoA, the first and rate-limiting step of de novo fatty acid biosynthesis. This is a 2 steps reaction starting with the ATP-dependent carboxylation of the biotin carried by the biotin carboxyl carrier (BCC) domain followed by the transfer of the carboxyl group from carboxylated biotin to acetyl-CoA.
Gene Name:: ACACA
Uniprot ID:: Q9TTS3
Molecular weight:: 265303.0

Reactions

Adenosine triphosphate + Hydrogen carbonate + Acetyl-CoA → Hydrogen phosphate + ADP + Malonyl-CoA	details
Acetyl-CoA → Malonyl-CoA	details

Enzyme Details

2. Fatty acid synthase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: Q71SP7
Molecular weight:: 274554.0

Reactions

Malonyl-CoA → Malonic acid + Coenzyme A	details

Enzyme Details

3. MLYCD protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: MLYCD
Uniprot ID:: A5PJC5
Molecular weight:: 55416.0

Reactions

Malonyl-CoA → Acetyl-CoA + Carbon dioxide	details

Showing metabocard for Malonyl-CoA (BMDB0001175)

Structure for BMDB0001175 (Malonyl-CoA)

Enzymes

Reactions

Reactions

Reactions