Showing Compound Acetyl-CoA (FDB022491)

Record Information

Version

1.0

Creation date

2011-09-21 00:14:50 UTC

Update date

2020-09-17 15:40:23 UTC

Primary ID

FDB022491

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetyl-CoA

Description

Acetyl-CoA, also known as acetyl coenzyme A or accoa, belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Thus, acetyl-CoA is considered to be a fatty ester lipid molecule. Acetyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acetyl-CoA exists in all living species, ranging from bacteria to humans. In humans, acetyl-CoA is involved in the metabolic disorder called the long chain acyl-coa dehydrogenase deficiency (lcad) pathway. An acyl-CoA having acetyl as its S-acetyl component. Outside of the human body, Acetyl-CoA has been detected, but not quantified in, several different foods, such as amaranths, lemon verbena, strawberries, lingonberries, and carobs. This could make acetyl-CoA a potential biomarker for the consumption of these foods.

CAS Number

72-89-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
AcCoA	ChEBI
Acetyl coenzyme A	ChEBI
S-Acetyl-CoA	ChEBI
S-Acetyl-coenzyme A	ChEBI
Ac-CoA	HMDB
Ac-coenzyme A	HMDB
Ac-S-CoA	HMDB
Ac-S-coenzyme A	HMDB
Acetyl-coenzyme A	HMDB
Acetyl-S-CoA	HMDB
Acetyl-S-coenzyme A	HMDB
Acetylcoenzyme A	HMDB
S-Acetate CoA	HMDB
S-Acetate coenzyme A	HMDB
S-Acetyl coenzyme A	HMDB
coenzyme A, Acetyl	HMDB
Acetyl CoA	HMDB
CoA, Acetyl	HMDB
ac-CoA	hmdb
ac-Coenzyme A	hmdb
ac-S-CoA	hmdb
ac-S-Coenzyme A	hmdb
acetyl coenzyme-A	hmdb
acetyl-CoA	hmdb
acetyl-Coenzyme A	hmdb
acetyl-S-CoA	hmdb
acetyl-S-Coenzyme A	hmdb
acetylcoenzyme-A	hmdb
S-acetate CoA	hmdb
S-acetate Coenzyme A	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	4.3 g/L	ALOGPS
logP	-0.58	ALOGPS
logP	-5.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	172.21 m³·mol⁻¹	ChemAxon
Polarizability	70.62 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

C23H38N7O17P3S

IUPAC name

{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

InChI Identifier

InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1

InChI Key

ZSLZBFCDCINBPY-ZSJPKINUSA-N

Isomeric SMILES

CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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

Average Molecular Weight

809.571

Monoisotopic Molecular Weight

809.125773051

Classification

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Glycosyl compound
O-glycosyl compound
Pyrrolidinylpyridine
Alkaloid or derivatives
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Oxane
Pyran
Pyridine
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Polyol
Acetal
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Biochemical process:

Role

Industrial application:

Biological role:

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	Acetyl-CoA, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetyl-CoA, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, positive	splash10-0fb9-0035910000-cecfaf54528fc3ef9f00	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, positive	splash10-0ufr-0005900000-491971eb7a5c2b327554	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-0a4i-0900000000-1b259612c3897ed851f0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-08i0-0001901200-8d4f5232c27f2875cf8b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-08i0-0000901200-33f8d3ced8c83336df0c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0a4i-1101800090-5031dc04edf8ba0f3afb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0a4i-1101900080-6691464da5a030f7d086	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0a4i-1101900080-8a1491c56fc1331c5df1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0a4i-1101900080-9ec3eecc20f19a822002	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1901000300-57c996f08055dba75dd7	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0902000000-dffb00601bfc54014ae4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2901000000-155f0890adf4c76dca85	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0arr-6820231930-984ae0f98e0d17e4a7fc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3910100000-87da6b6d742efbc6e74a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900000000-8701decc3b2311880b97	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000090-fd17a06b039262f96463	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05vx-9100203430-9e39d5da3afdd3a15f91	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00b9-9101401200-719cb55952a06d96d3c8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-02de4c2ee732e6d50b2d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-1901002440-79ee9e61778bd08a750f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0209000000-84f7f68fc2e83a8ae770	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

392413

ChEMBL ID

Not Available

KEGG Compound ID

C00024

Pubchem Compound ID

444493

Pubchem Substance ID

Not Available

ChEBI ID

15351

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01206

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

33558

KNApSAcK ID

Not Available

HET ID

ACO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Acetyl-CoA

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
Carnitine O-acetyltransferase	CRAT	P43155
Hepatic triacylglycerol lipase	LIPC	P11150
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
Malonyl-CoA decarboxylase, mitochondrial	MLYCD	O95822
Fatty acid synthase	FASN	P49327
Sterol O-acyltransferase 1	SOAT1	P35610
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Long-chain fatty acid transport protein 3	SLC27A3	Q5K4L6
Long-chain fatty acid transport protein 4	SLC27A4	Q6P1M0
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
Diacylglycerol O-acyltransferase 2-like protein 6	DGAT2L6	Q6ZPD8
Putative diacylglycerol O-acyltransferase 2-like protein 7	DGAT2L7	Q6IED9
Acyl-CoA-binding protein	DBI	P07108
Peroxisome proliferator-activated receptor delta	PPARD	Q03181
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-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	P21953
Arylamine N-acetyltransferase 1	NAT1	P18440
Arylamine N-acetyltransferase 2	NAT2	P11245
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
Hydroxymethylglutaryl-CoA lyase, mitochondrial	HMGCL	P35914
Acyl-coenzyme A thioesterase 12	ACOT12	Q8WYK0
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
Peroxisomal trans-2-enoyl-CoA reductase	PECR	Q9BY49
N-acetylglutamate synthase, mitochondrial	NAGS	Q8N159
Nuclear receptor coactivator 3	NCOA3	Q9Y6Q9
Bile acyl-CoA synthetase	SLC27A5	Q9Y2P5
Sterol O-acyltransferase 2	SOAT2	O75908
Acyl-CoA synthetase family member 4	AASDH	Q4L235
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
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic	HMGCLL1	Q8TB92
Very long-chain acyl-CoA synthetase	SLC27A2	O14975
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
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
Peroxisome proliferator-activated receptor alpha	PPARA	Q07869
Fatty acid-binding protein, heart	FABP3	P05413
Acyl-CoA dehydrogenase family member 10	ACAD10	Q6JQN1
Acyl-CoA dehydrogenase family member 11	ACAD11	Q709F0
Lysophospholipid acyltransferase LPCAT4	LPCAT4	Q643R3
Enoyl-CoA delta isomerase 2, mitochondrial	ECI2	O75521
Nef-associated protein 1	C9orf156	Q9BU70
Acyl-coenzyme A thioesterase 9, mitochondrial	ACOT9	Q9Y305
Acyl-CoA synthetase family member 3, mitochondrial	ACSF3	Q4G176
Acyl-CoA synthetase family member 2, mitochondrial	ACSF2	Q96CM8
Acyl-coenzyme A thioesterase 11	ACOT11	Q8WXI4
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
Acetyl-coenzyme A transporter 1	SLC33A1	O00400
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

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
Butyrate Metabolism	SMP00073	map00650
Citric Acid Cycle	SMP00057	map00020
Ethanol Degradation	SMP00449	Not Available
Fatty Acid Biosynthesis	SMP00456	Not Available
Fatty acid Metabolism	SMP00051	map00071
Glycine and Serine Metabolism	SMP00004	map00260
Ketone Body Metabolism	SMP00071	map00072
Lysine Degradation	SMP00037	map00310
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
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Propanoate Metabolism	SMP00016	map00640
Pyruvate Metabolism	SMP00060	map00620
Steroid Biosynthesis	SMP00023	map00100
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Valine, Leucine and Isoleucine Degradation	SMP00032	map00280