Showing Compound Coenzyme A (FDB022614)

Record Information

Version

1.0

Creation date

2011-09-21 00:16:54 UTC

Update date

2019-11-26 03:21:04 UTC

Primary ID

FDB022614

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Coenzyme A

Description

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia [HMDB]. Coenzyme A is found in many foods, some of which are grape, cowpea, pili nut, and summer savory.

CAS Number

85-61-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
CoA	MeSH
CoASH	MeSH
Acetoacetyl coenzyme A sodium salt	HMDB
CoA Hydrate	HMDB
CoA-SH	HMDB
coenzyme A Hydrate	HMDB
coenzyme A-SH	HMDB
coenzyme ASH	HMDB
Coenzymes a	HMDB
Depot-zeel	HMDB
Propionyl CoA	HMDB
Propionyl coenzyme A	HMDB
S-Propanoate	HMDB
S-Propanoate CoA	HMDB
S-Propanoate coenzyme A	HMDB
S-Propanoic acid	HMDB
S-Propionate CoA	HMDB
S-Propionate coenzyme A	HMDB
Zeel	HMDB
[(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate	HMDB
a, Coenzyme	MeSH
[(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(onooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diate	HMDB
[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate	hmdb
CoA hydrate	hmdb
Coenzyme A	hmdb
Coenzyme A hydrate	hmdb
Coenzyme A-SH	hmdb
Coenzyme ASH	hmdb
coenzymes A	hmdb
Depot-Zeel	hmdb
Propionyl Coenzyme A	hmdb
S-propanoate	hmdb
S-propanoate CoA	hmdb
S-propanoate Coenzyme A	hmdb
S-propanoic acid	hmdb
S-propionate CoA	hmdb
S-propionate Coenzyme A	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	5.35 g/L	ALOGPS
logP	-0.63	ALOGPS
logP	-5.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	346.56 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	162.74 m³·mol⁻¹	ChemAxon
Polarizability	66.82 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

Chemical Formula

C21H36N7O16P3S

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-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

InChI Identifier

InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1

InChI Key

RGJOEKWQDUBAIZ-DRCCLKDXSA-N

Isomeric 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)NCCS

Average Molecular Weight

767.534

Monoisotopic Molecular Weight

767.115208365

Classification

Description

Belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Coenzyme A and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Coenzyme A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9423572000-e15b71f4fd7a2baa5a35	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0000000900-7edeffc9e7f47049c6af	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0090200000-1bf2c11b25a8c3f528a7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03di-0490000000-b4270769e635660752dd	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002s-5900000100-c920e6430f49f066a644	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-6910000000-4dcac54e50dd5309af5c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-8900000000-c9fc1dcc0fa2fecbf2f0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-6910232700-7e01b474d15249f13f3e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900200000-23c6af6438be416c3b4e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-a9a1d2f2162117f6ad81	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15346

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01423

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

33502

KNApSAcK ID

Not Available

HET ID

1A59

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Coenzyme A

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Glycine N-acyltransferase	GLYAT	Q6IB77
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Glycine N-acyltransferase-like protein 2	GLYATL2	Q8WU03
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial	GCAT	O75600
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Serine palmitoyltransferase 1	SPTLC1	O15269
Carnitine O-acetyltransferase	CRAT	P43155
Peroxisomal carnitine O-octanoyltransferase	CROT	Q9UKG9
Carnitine O-palmitoyltransferase 1, muscle isoform	CPT1B	Q92523
Carnitine O-palmitoyltransferase 1, liver isoform	CPT1A	P50416
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	P23786
Carnitine O-palmitoyltransferase 1, brain isoform	CPT1C	Q8TCG5
Diacylglycerol O-acyltransferase 1	DGAT1	O75907
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
Diacylglycerol O-acyltransferase 2	DGAT2	Q96PD7
2-acylglycerol O-acyltransferase 1	MOGAT1	Q96PD6
2-acylglycerol O-acyltransferase 3	MOGAT3	Q86VF5
Glycerol-3-phosphate acyltransferase 3	AGPAT9	Q53EU6
Choline O-acetyltransferase	CHAT	P28329
Fatty acyl-CoA reductase 2	FAR2	Q96K12
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Q6E213
Serotonin N-acetyltransferase	AANAT	Q16613
ATP-citrate synthase	ACLY	P53396
Citrate synthase, mitochondrial	CS	O75390
Diamine acetyltransferase 2	SAT2	Q96F10
Diamine acetyltransferase 1	SAT1	P21673
Fatty acid synthase	FASN	P49327
Sterol O-acyltransferase 1	SOAT1	P35610
Lysosomal thioesterase PPT2	PPT2	Q9UMR5
Fatty acyl-CoA reductase 1	FAR1	Q8WVX9
Acyl-CoA wax alcohol acyltransferase 1	AWAT1	Q58HT5
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Pyruvate dehydrogenase E1 component subunit beta, mitochondrial	PDHB	P11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	PDHA1	P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial	PDHA2	P29803
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	Q02218
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL	Q9ULD0
Arylamine N-acetyltransferase 1	NAT1	P18440
Arylamine N-acetyltransferase 2	NAT2	P11245
3-hydroxy-3-methylglutaryl-coenzyme A reductase	HMGCR	P04035
Ceramide synthase 1	CERS1	P27544
Phosphatidylinositol-glycan biosynthesis class W protein	PIGW	Q7Z7B1
Acetyl-coenzyme A synthetase, cytoplasmic	ACSS2	Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrial	ACSS1	Q9NUB1
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial	DLAT	P10515
Acyl-coenzyme A thioesterase 12	ACOT12	Q8WYK0
Palmitoyl-protein thioesterase 1	PPT1	P50897
Cytosolic acyl coenzyme A thioester hydrolase-like	ACOT7L	Q6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2	ACSBG2	Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1	ACSBG1	Q96GR2
Nuclear receptor coactivator 1	NCOA1	Q15788
3-ketoacyl-CoA thiolase, mitochondrial	ACAA2	P42765
Elongation of very long chain fatty acids protein 4	ELOVL4	Q9GZR5
N-acetylglutamate synthase, mitochondrial	NAGS	Q8N159
Nuclear receptor coactivator 3	NCOA3	Q9Y6Q9
Serine palmitoyltransferase 2	SPTLC2	O15270
Serine palmitoyltransferase 3	SPTLC3	Q9NUV7
Bile acyl-CoA synthetase	SLC27A5	Q9Y2P5
Sterol O-acyltransferase 2	SOAT2	O75908
Bifunctional coenzyme A synthase	COASY	Q13057
Acetoacetyl-CoA synthetase	AACS	Q86V21
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	HIBCH	Q6NVY1
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferase	AASDHPPT	Q9NRN7
Hydroxymethylglutaryl-CoA synthase, mitochondrial	HMGCS2	P54868
Hydroxymethylglutaryl-CoA synthase, cytoplasmic	HMGCS1	Q01581
3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial	OXSM	Q9NWU1
Glycerol-3-phosphate acyltransferase 1, mitochondrial	GPAM	Q9HCL2
Glycerol-3-phosphate acyltransferase 4	AGPAT6	Q86UL3
Glycerol-3-phosphate acyltransferase 2, mitochondrial	GPAT2	Q6NUI2
Very long-chain acyl-CoA synthetase	SLC27A2	O14975
Non-specific lipid-transfer protein	SCP2	P22307
Lysophospholipid acyltransferase 5	LPCAT3	Q6P1A2
Lysophosphatidylcholine acyltransferase 2	LPCAT2	Q7L5N7
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma	AGPAT3	Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase beta	AGPAT2	O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alpha	AGPAT1	Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon	AGPAT5	Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase delta	AGPAT4	Q9NRZ5
Lysocardiolipin acyltransferase 1	LCLAT1	Q6UWP7
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial	DLST	P36957
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	DBT	P11182
3-ketoacyl-CoA thiolase, peroxisomal	ACAA1	P09110
Trifunctional enzyme subunit beta, mitochondrial	HADHB	P55084
Dihydroxyacetone phosphate acyltransferase	GNPAT	O15228
Glucosamine 6-phosphate N-acetyltransferase	GNPNAT1	Q96EK6
Acetyl-CoA acetyltransferase, cytosolic	ACAT2	Q9BWD1
Acetyl-CoA acetyltransferase, mitochondrial	ACAT1	P24752
General transcription factor 3C polypeptide 4	GTF3C4	Q9UKN8
Histone acetyltransferase KAT2B	KAT2B	Q92831
Testis-specific chromodomain protein Y 1	CDY1	Q9Y6F8
Histone acetyltransferase KAT5	KAT5	Q92993
Testis-specific chromodomain protein Y 2	CDY2A	Q9Y6F7
Histone acetyltransferase KAT2A	KAT2A	Q92830
Histone acetyltransferase KAT6B	KAT6B	Q8WYB5
MYST3 protein	MYST3	A5PKX7
Histone acetyltransferase KAT8	KAT8	Q9H7Z6
Histone acetyltransferase type B catalytic subunit	HAT1	O14929
Chromodomain Y-like protein	CDYL	Q9Y232
Circadian locomoter output cycles protein kaput	CLOCK	O15516
Histone acetyltransferase KAT7	KAT7	O95251
Malonyl-CoA-acyl carrier protein transacylase, mitochondrial	MCAT	Q8IVS2
Glycylpeptide N-tetradecanoyltransferase 1	NMT1	P30419
Glycylpeptide N-tetradecanoyltransferase 2	NMT2	O60551

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Beta Oxidation of Very Long Chain Fatty Acids	SMP00052	map01040
Beta-Alanine Metabolism	SMP00007	map00410
Bile Acid Biosynthesis	SMP00035	map00120
Butyrate Metabolism	SMP00073	map00650
Citric Acid Cycle	SMP00057	map00020
Ethanol Degradation	SMP00449	Not Available
Fatty acid Metabolism	SMP00051	map00071
Glycine and Serine Metabolism	SMP00004	map00260
Ketone Body Metabolism	SMP00071	map00072
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids	SMP00482	Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids	SMP00481	Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids	SMP00480	Not Available
Oxidation of Branched Chain Fatty Acids	SMP00030	Not Available
Pantothenate and CoA Biosynthesis	SMP00027	map00770
Phenylacetate Metabolism	SMP00126	map00360
Plasmalogen Synthesis	SMP00479	Not Available
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available