ECMDB: 3-Hydroxy-5-methylhex-4-enoyl-CoA (ECMDB20071) (M2MDB000920)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (1)XML

Proteins (437)

Record Information

Version

2.0

Creation Date

2012-05-31 14:25:57 -0600

Update Date

2015-06-03 17:19:15 -0600

Secondary Accession Numbers

ECMDB20071

Identification

Name:

3-Hydroxy-5-methylhex-4-enoyl-CoA

Description

3-hydroxy-5-methylhex-4-enoyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Not Available

Chemical Formula:

C₂₈H₄₆N₇O₁₈P₃S

Weight:

Average: 893.687
Monoisotopic: 893.183287929

InChI Key:

OLZYNLSKRKFUJC-GPZVIVARSA-N

InChI:

InChI=1S/C28H46N7O18P3S/c1-15(2)9-16(36)10-19(38)57-8-7-30-18(37)5-6-31-26(41)23(40)28(3,4)12-50-56(47,48)53-55(45,46)49-11-17-22(52-54(42,43)44)21(39)27(51-17)35-14-34-20-24(29)32-13-33-25(20)35/h9,13-14,16-17,21-23,27,36,39-40H,5-8,10-12H2,1-4H3,(H,30,37)(H,31,41)(H,45,46)(H,47,48)(H2,29,32,33)(H2,42,43,44)/t16?,17-,21-,22-,23?,27-/m1/s1

CAS number:

Not Available

IUPAC Name:

4-({[({[(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)-2-hydroxy-N-[2-({2-[(3-hydroxy-5-methylhex-4-enoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid

Traditional IUPAC Name:

4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-[2-({2-[(3-hydroxy-5-methylhex-4-enoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid

SMILES:

[H]C(O)(CC(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O)C=C(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetaldehydes

Direct Parent

Phenylacetaldehydes

Alternative Parents

Substituents

Phenylacetaldehyde
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylacetaldehydes (CHEBI:80586 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.9 g/L	ALOGPS
logP	-0.34	ALOGPS
logP	-5.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.94	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	390.84 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	198.44 m³·mol⁻¹	ChemAxon
Polarizability	81.93 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:

(2E)-5-Methylhexa-2,4-dienoyl-CoA + Water <> 3-Hydroxy-5-methylhex-4-enoyl-CoA
3-Hydroxy-5-methylhex-4-enoyl-CoA + NAD <> 5-Methyl-3-oxo-4-hexenoyl-CoA + NADH + Hydrogen ion

SMPDB Pathways:

Not Available

KEGG Pathways:

Geraniol degradation ec00281

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-1971000230-fd1d24bc4747cd663ec4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0962000000-c563617e84ad4417f7dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2950000000-e8b95d7af80e2611e844	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-5910041460-0b5a6d7f63b3f87260ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3910120010-f7b6f0e376b5c79d0cb8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-b169ec88547cd138f059	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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	80512
HMDB ID	Not Available
Pubchem Compound ID	23724759
Kegg ID	C16469
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

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. 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.

3-Hydroxy-5-methylhex-4-enoyl-CoA (ECMDB20071) (M2MDB000920)

Structure for #<Compound:0x988835b8>

Enzymes

Reactions

Reactions

Reactions

Transporters

Reactions