Showing Compound Isobutyryl-CoA (FDB022508)

Record Information

Version

1.0

Creation date

2011-09-21 00:15:05 UTC

Update date

2020-09-17 15:38:51 UTC

Primary ID

FDB022508

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isobutyryl-CoA

Description

Isobutyryl-CoA, also known as isobutanoyl-CoA, 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. Thus, isobutyryl-CoA is considered to be a fatty ester lipid molecule. Isobutyryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

15621-60-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Methylpropanoyl-CoA	ChEBI
2-Methylpropionyl-CoA	ChEBI
Isobutanoyl-CoA	ChEBI
2-Methylpropanoyl-coenzyme A	HMDB
2-Methylpropionyl-coenzyme A	HMDB
alpha-Methylpropionyl-CoA	HMDB
alpha-Methylpropionyl-coenzyme A	HMDB
Isobutyryl- CoA	HMDB
Isobutyryl- coenzyme A	HMDB
S-(2-Methylpropanoate	HMDB
S-(2-Methylpropanoate)CoA	HMDB
S-(2-Methylpropanoate)coenzyme A	HMDB
S-(2-Methylpropanoic acid	HMDB
S-(2-Methylpropanoyl)-CoA	HMDB
S-(2-Methylpropanoyl)-coenzyme A	HMDB
Isobutyryl-coenzyme A	HMDB
2-Methylpropanoyl-Coenzyme A	hmdb
2-Methylpropionyl-Coenzyme A	hmdb
alpha-methylpropionyl-CoA	hmdb
alpha-methylpropionyl-Coenzyme A	hmdb
Isobutyryl- Coenzyme A	hmdb
Isobutyryl-coA	hmdb
S-(2-methylpropanoate	hmdb
S-(2-methylpropanoate)CoA	hmdb
S-(2-methylpropanoate)Coenzyme A	hmdb
S-(2-methylpropanoic acid	hmdb
S-(2-methylpropanoyl)-CoA	hmdb
S-(2-methylpropanoyl)-Coenzyme A	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	3.87 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-4.6	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	21	ChemAxon
Refractivity	181.41 m³·mol⁻¹	ChemAxon
Polarizability	75.44 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

C25H42N7O17P3S

IUPAC name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

InChI Identifier

InChI=1S/C25H42N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,34-35H,5-10H2,1-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19+,23-/m1/s1

InChI Key

AEWHYWSPVRZHCT-NDZSKPAWSA-N

Isomeric SMILES

CC(C)C(=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

837.624

Monoisotopic Molecular Weight

837.157073179

Classification

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 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
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
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl-branched fatty acyl-CoA (CHEBI:15479 )
short-chain fatty acyl-CoA (CHEBI:15479 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

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
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive	splash10-0019-1319100060-a79bd8a602e60d66ac13	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-001i-0119200000-4e679a7c24abcdc11da3	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-000i-1100400090-8f145af0c5b7cd4ac4a4	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-0a4r-0001900230-95377ad2588da2829d5e	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4r-0001900230-0d57be779009a47b3dba	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0119200000-78faf0478e7c602748b8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0119200000-45aa20fbcdd1e63a894f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4r-0001900230-90449190d7f5d676ef23	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000120-f55c632bcd1b333334d4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1912000000-8cde39bfd4a461090f5a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-c7b1d9c988c6f8b3f8d2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9830141650-f43324cd35c202d513cf	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00o0-4910100010-f378cf8a3791bc14e286	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-40bc8264c1477ec9f667	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000090-073f428b330788172433	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-9700001110-c5e67605cae198ee7c6f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00n0-7104504900-a408436d4349ab93733f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-1c2a17ed106a9fe34338	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3910002340-52078e31983e5f0f6f21	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0129000000-230d4ae4be019648dc20	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

2300823

ChEMBL ID

Not Available

KEGG Compound ID

C00630

Pubchem Compound ID

3036931

Pubchem Substance ID

Not Available

ChEBI ID

15479

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01243

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

35538

KNApSAcK ID

Not Available

HET ID

CO6

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

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
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
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
Fatty acyl-CoA reductase 2	FAR2	Q96K12
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Q6E213
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
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	P21953
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
3-ketoacyl-CoA thiolase, mitochondrial	ACAA2	P42765
Peroxisomal trans-2-enoyl-CoA reductase	PECR	Q9BY49
Bile acyl-CoA synthetase	SLC27A5	Q9Y2P5
Sterol O-acyltransferase 2	SOAT2	O75908
Acyl-CoA synthetase family member 4	AASDH	Q4L235
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
Lysophospholipid acyltransferase 5	LPCAT3	Q6P1A2
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