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Record Information

Version

2.0

Creation Date

2012-05-31 13:46:40 -0600

Update Date

2015-09-17 15:41:10 -0600

Secondary Accession Numbers

ECMDB01166

Identification

Name:

3-Hydroxybutyryl-CoA

Description

3-Hydroxybutyryl-CoA or 3-hydroxybutyryl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-hydroxybutyryl-S-CoA
β-hydroxybutyryl-CoA
β-hydroxybutyryl-s-CoA
(3R)-3-Hydroxybutanoyl-CoA
(3R)-3-Hydroxybutanoyl-Coenzyme A
(R)-3-Hydroxybutanoyl-CoA
(R)-3-Hydroxybutanoyl-Coenzyme A
(S)-3-hydroxybutanoyl-CoA
(S)-3-hydroxybutanoyl-Coenzyme A
3-Hydroxybutanoyl-CoA
3-Hydroxybutanoyl-coenzyme a
3-Hydroxybutyryl-CoA
3-Hydroxybutyryl-coenzyme A
3-OH-butyryl-CoA
3-OH-butyryl-Coenzyme A
b-Hydroxybutyryl-CoA
b-Hydroxybutyryl-coenzyme A
b-Hydroxybutyryl-S-CoA
b-Hydroxybutyryl-S-coenzyme A
Beta-Hydroxybutyryl-CoA
Beta-Hydroxybutyryl-Coenzyme A
Beta-Hydroxybutyryl-S-CoA
Beta-Hydroxybutyryl-S-Coenzyme A
D-3-Hydroxybutyryl-CoA
Hydroxy-butyryl-CoA
Hydroxy-butyryl-Coenzyme A
OH-butyryl-CoA
β-Hydroxybutyryl-CoA
β-Hydroxybutyryl-coenzyme A
β-Hydroxybutyryl-S-CoA
β-Hydroxybutyryl-S-coenzyme A

Chemical Formula:

C₂₅H₄₂N₇O₁₈P₃S

Weight:

Average: 853.623
Monoisotopic: 853.151987801

InChI Key:

QHHKKMYHDBRONY-JYMPOPDUSA-N

InChI:

InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1

CAS number:

2871-66-1

IUPAC Name:

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

Traditional IUPAC Name:

(S)-3-hydroxybutanoyl-coa

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(S)-3-hydroxyacyl 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

3-hydroxybutanoyl-CoA (CHEBI:15453 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.13 g/L	ALOGPS
logP	-0.49	ALOGPS
logP	-6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	183.03 m³·mol⁻¹	ChemAxon
Polarizability	77.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Fatty acid metabolism	PW000796
Phenylalanine metabolism	PW000921
fatty acid oxidation (Butanoate)	PW001017

KEGG Pathways:

Benzoate degradation via CoA ligation ec00632
Benzoate degradation via hydroxylation ec00362
Butanoate metabolism ec00650
Fatty acid metabolism ec00071
Glyoxylate and dicarboxylate metabolism ec00630
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Phenylalanine metabolism ec00360

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0931000130-23f3e172cccb46516046	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-1912000000-399c515245dec6a2cc71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-1920000000-8fe1c131ac5ed900f9ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-9720051570-ac103b1d89e177e590b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5910120010-ac00f635f518b7677a1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-5fd723fafb9eda8bd257	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000190-d4aa33b196af72ac06cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-1301102790-5031f947450e97f8dc8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0039000000-2c32496eb9d5b677d278	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000190-8fba08e29a0129c20131	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00gu-9500106840-70232b0f4b23ef5ffa0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fms-9000422600-94c159b363bfe9e117f6	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15452
HMDB ID	HMDB01166
Pubchem Compound ID	521
Kegg ID	C01144
ChemSpider ID	389056
Wikipedia	beta-hydroxybutyryl-CoA
BioCyc ID	CPD-650
EcoCyc ID	CPD-650
Ligand Expo	3HC

Enzymes

Protein Details

1. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

Protein Details

2. Probable enoyl-CoA hydratase paaF

General function:: Involved in catalytic activity
Specific function:: Could possibly oxidize fatty acids using specific components
Gene Name:: paaF
Uniprot ID:: P76082
Molecular weight:: 27237

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.

Protein Details

3. Probable 3-hydroxybutyryl-CoA dehydrogenase

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: (S)-3-hydroxybutanoyl-CoA + NADP(+) = 3- acetoacetyl-CoA + NADPH
Gene Name:: paaH
Uniprot ID:: P76083
Molecular weight:: 51732

Reactions

(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3-acetoacetyl-CoA + NADPH.

Protein Details

4. Fatty acid oxidation complex subunit alpha_

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:: fadJ
Uniprot ID:: P77399
Molecular weight:: 77072

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

Protein Details

1. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

3-Hydroxybutyryl-CoA (M2MDB000280)

Structure for #<Compound:0x9a35ba48>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters

Reactions