P. aeruginosa Metabolome Database: Octadecenoyl-CoA (N-C18:1CoA) (PAMDB001668)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001668

Identification

Name:

Octadecenoyl-CoA (N-C18:1CoA)

Description:

Octadecenoyl-coa (n-c18:1coa) belongs to the class of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. (inferred from compound structure)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Not Available

Chemical Formula:

C₃₉H₆₄N₇O₁₇P₃S

Average Molecular Weight:

1027.948

Monoisotopic Molecular Weight:

1027.329223883

InChI Key:

NBCCUIHOHUKBMK-KBEKLFCESA-J

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)/p-4/t28-,32-,33-,34?,38-/m1/s1

CAS number:

Not Available

IUPAC Name:

4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(octadec-2-enoylsulfanyl)ethyl]carboximidato}ethyl)butanecarboximidate

Traditional IUPAC Name:

4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-(octadec-2-enoylsulfanyl)ethyl]carboximidato}ethyl)butanecarboximidate

SMILES:

[H]C(O)(C([O-])=NCCC([O-])=NCCSC(=O)C=CCCCCCCCCCCCCCCC)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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Oxolane
Imidazole
Azole
Thiocarboxylic acid ester
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.184 mg/mL	ALOGPS
logP	4.13	ALOGPS
logP	1.01	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.93	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	381.93 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	266.84 m³·mol^-1	ChemAxon
Polarizability	103.12 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:

Adenosine triphosphate + Coenzyme A + Hydrogen ion + Octadecenoate (N-C18:1) > Adenosine monophosphate + Hydrogen ion + Octadecenoyl-CoA (N-C18:1CoA) + Pyrophosphate
Water + Octadecenoyl-CoA (N-C18:1CoA) > Coenzyme A + Hydrogen ion + Octadecenoate (N-C18:1)
Octadecenoyl-CoA (N-C18:1CoA) <> Trans-Octadec-2-enoyl-CoA
Glycerol 3-phosphate + Octadecenoyl-CoA (N-C18:1CoA) > LPA(18:1(9Z)/0:0) + Coenzyme A
LPA(18:1(9Z)/0:0) + Octadecenoyl-CoA (N-C18:1CoA) > DG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/0:0) + Coenzyme A

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-9000000100-45da66982338e6b3a083	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-9000010000-4d4fe998690f367ac429	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9711500100-bc84e1d3c2099a79fea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-4c1da2ce4b4980ec6010	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003i-9060010000-f7fd4fd491c33ebb472e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rt-9400000000-f21f4a8506c925cc0b8b	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-2227
EcoCyc ID	CPD0-2227

Enzymes

Protein Details

• Glycerol-3-phosphate acyltransferase

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:: plsB
Locus Tag:: PA3673
Molecular weight:: 94.8 kDa

Reactions

Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.

Protein Details

• 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
Locus Tag:: PA3014
Molecular weight:: 77 kDa

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

• Long-chain-fatty-acid--CoA ligase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:: fadD
Locus Tag:: PA3299
Molecular weight:: 61.7 kDa

Reactions

ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.

Protein Details

• 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
Locus Tag:: PA3942
Molecular weight:: 32.9 kDa

Octadecenoyl-CoA (N-C18:1CoA) (PAMDB001668)

Structure for Octadecenoyl-CoA (N-C18:1CoA) (PAMDB001668)

Enzymes

Reactions

Reactions

Reactions