ECMDB: 2-Oxepin-2(3H)-ylideneacetyl-CoA (ECMDB21164) (M2MDB001573)

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

Proteins (191)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:43 -0600

Update Date

2015-06-03 17:20:47 -0600

Secondary Accession Numbers

ECMDB21164

Identification

Name:

2-Oxepin-2(3H)-ylideneacetyl-CoA

Description

2-Oxepin-2(3h)-ylideneacetyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Oxepin-CoA

Chemical Formula:

C₂₉H₄₂N₇O₁₈P₃S

Weight:

Average: 901.666
Monoisotopic: 901.151987801

InChI Key:

ZQZCWPBSHHYCMM-BETJHJQZSA-N

InChI:

InChI=1S/C29H42N7O18P3S/c1-29(2,24(40)27(41)32-8-7-19(37)31-9-11-58-20(38)12-17-6-4-3-5-10-49-17)14-51-57(47,48)54-56(45,46)50-13-18-23(53-55(42,43)44)22(39)28(52-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-5,10,12,15-16,18,22-24,28,39-40H,6-9,11,13-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/b17-12-/t18-,22-,23-,24+,28-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

oxepin-CoA

SMILES:

O[C@H](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)C(=O)NCCC(=O)NCCSC(=O)\C=C1\CC=CC=CO1

Chemical Taxonomy

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
Aminopyrimidine
Monoalkyl phosphate
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Imidolactam
Pyrimidine
Imidazole
Azole
Vinylogous ester
Heteroaromatic compound
Tetrahydrofuran
Amino acid or derivatives
Thiocarboxylic acid ester
Carbothioic s-ester
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
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

acyl-CoA (CHEBI:63251 )

Physical Properties

State:

Not Available

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.73 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-5.8	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	372.86 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	202.61 m³·mol⁻¹	ChemAxon
Polarizability	79.7 Å³	ChemAxon
Number of Rings	4	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:

Collection of Reactions without pathways	PW001891
Fatty acid metabolism	PW000796
Phenylalanine metabolism	PW000921
Phenylethylamine metabolism	PW002027
Propanoate metabolism	PW000940
Tryptophan metabolism	PW000815
beta-Alanine metabolism	PW000896

KEGG Pathways:

Benzoate degradation via CoA ligation ec00632
Biosynthesis of unsaturated fatty acids ec01040
Butanoate metabolism ec00650
Caprolactam degradation ec00930
Fatty acid elongation in mitochondria ec00062
Fatty acid metabolism ec00071
Geraniol degradation ec00281
Limonene and pinene degradation ec00903
Lysine degradation ec00310
Microbial metabolism in diverse environments ec01120
Phenylalanine metabolism ec00360
Propanoate metabolism ec00640
Tryptophan metabolism ec00380
Valine, leucine and isoleucine degradation ec00280
alpha-Linolenic acid metabolism ec00592
beta-Alanine metabolism ec00410

EcoCyc Pathways:

phenylacetate degradation I (aerobic) PWY0-321

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000120-ac12d68d414245d8ccfa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0933000000-28af69d86b4b2c5eb4b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-7d58a53ead7fe5d17826	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-2911030222-69dc55286d1a6485804f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3910010010-786c7725eccfa0940350	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-a900dc3ca65cd722406d	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:

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	63251
HMDB ID	Not Available
Pubchem Compound ID	53377481
Kegg ID	C19975
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-2363
EcoCyc ID	CPD0-2363

Enzymes

Protein Details

1. 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

2. Probable enoyl-CoA hydratase paaG

General function:: Involved in catalytic activity
Specific function:: Could possibly oxidize fatty acids using specific components
Gene Name:: paaG
Uniprot ID:: P77467
Molecular weight:: 28404

Reactions

2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA = 2-oxepin-2(3H)-ylideneacetyl-CoA.

Protein Details

3. Protein maoC

General function:: Involved in oxidoreductase activity
Specific function:: Specific function unknown
Gene Name:: maoC
Uniprot ID:: P77455
Molecular weight:: 73002

Reactions

2-oxepin-2(3H)-ylideneacetyl-CoA + H(2)O = 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde.
3-oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP(+) + H(2)O = 3-oxo-5,6-dehydrosuberyl-CoA + NADPH.

2-Oxepin-2(3H)-ylideneacetyl-CoA (ECMDB21164) (M2MDB001573)

Structure for #<Compound:0xa4d70f4c>

Enzymes

Reactions

Reactions

Reactions