ECMDB: Trans-Octadec-2-enoyl-CoA (ECMDB21363) (M2MDB001759)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)Transporters (1)XML

Proteins (5)

Record Information

Version

2.0

Creation Date

2012-07-30 14:55:30 -0600

Update Date

2015-09-17 15:41:20 -0600

Secondary Accession Numbers

ECMDB21363

Identification

Name:

Trans-Octadec-2-enoyl-CoA

Description

trans-Octadec-2-enoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. trans-Octadec-2-enoyl-CoA is produced from 3-Hydroxyoctadecanoyl-CoA and then converted to Stearoyl-CoA via enzymatic reaction.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2E)-octadecenoyl-CoA
(2E)-Octadecenoyl-CoA
(2E)-Octadecenoyl-Coenzyme A
(E)-2-octadecenoyl-CoA
(E)-2-octadecenoyl-coenzyme A
(E)-octadec-2-enoyl-CoA
(E)-octadec-2-enoyl-coenzyme A
3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
trans-2,3-dihydro-stearenoyl-CoA
Elaidate coenzyme a
Elaidic acid coenzyme a
Trans-2,3-Dihydro-stearenoyl-CoA
Trans-Octadec-2-enoyl-CoA
Trans-Octadec-2-enoyl-coenzyme A

Chemical Formula:

C₃₉H₆₈N₇O₁₇P₃S

Weight:

Average: 1031.98
Monoisotopic: 1031.360524011

InChI Key:

NBCCUIHOHUKBMK-XCRBYWPRSA-N

InChI:

InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h18-19,26-28,32-34,38,49-50H,4-17,20-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b19-18+/t28-,32?,33+,34+,38-/m1/s1

CAS number:

Not Available

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-[(2E)-octadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name:

trans-octadec-2-enoyl-coa

SMILES:

CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Secondary carboxylic acid amides

Alternative Parents

Substituents

Secondary carboxylic acid amide
Secondary alcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	2.87	ALOGPS
logP	1.72	ChemAxon
logS	-3.1	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	35	ChemAxon
Refractivity	246.94 m³·mol⁻¹	ChemAxon
Polarizability	105.18 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:

(S)-3-Hydroxyoctadecanoyl-CoA <> Water + Trans-Octadec-2-enoyl-CoA
FAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoA
Octadecenoyl-CoA (N-C18:1CoA) <> Trans-Octadec-2-enoyl-CoA
trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + Water
(S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA
trans-Octadec-2-enoyl-CoA + Water + Trans-Octadec-2-enoyl-CoA > Coenzyme A + Hydrogen ion + Elaidic acid

SMPDB Pathways:

fatty acid oxidation (steareate)

PW001024

KEGG Pathways:

Not Available

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-3902020100-702c8c6bb21cd9180926	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0913030000-9429405f3ae0c38fbca4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010100-0d3539439cc41d679212	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-9661431500-bb443918c6c1478b7d50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-4930210000-e27b2dee0f4b40981f33	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900000000-09fe7ed24018a4548742	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-cfe800ad5bbc58e06114	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-9010201300-6e87805c7ac31cddea17	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9102400305-4e9310c03d5744a7e414	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-23e10589819478bd138f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4700100319-38af1792f0bfce070d96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0100790000-0dd953635f26c9b0d42d	View in MoNA
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:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	50570
HMDB ID	HMDB06529
Pubchem Compound ID	23724662
Kegg ID	C16218
ChemSpider ID	21865759
Wikipedia ID	Not Available
BioCyc ID	CPD-10262
EcoCyc ID	CPD-10262

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.

Protein Details

4. Acyl-coenzyme A dehydrogenase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the dehydrogenation of acyl-CoA
Gene Name:: fadE
Uniprot ID:: Q47146
Molecular weight:: 89224

Reactions

An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).

Protein Details

5. Acyl-CoA thioesterase 2

General function:: Involved in acyl-CoA hydrolase activity
Specific function:: Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:: tesB
Uniprot ID:: P0AGG2
Molecular weight:: 31966

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.

Trans-Octadec-2-enoyl-CoA (ECMDB21363) (M2MDB001759)

Structure for #<Compound:0xab0ac2f0>

Enzymes

Reactions

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Transporters

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