P. aeruginosa Metabolome Database: (3S)-3-Hydroxyadipyl-CoA (PAMDB000859)

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

PAMDB000859

Identification

Name:

(3S)-3-Hydroxyadipyl-CoA

Description:

(3s)-3-hydroxyadipyl-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 View Structure

Synonyms:

(3S)-3-Hydroxyadipyl-CoEnzyme A

Chemical Formula:

C₂₇H₄₄N₇O₂₀P₃S

Average Molecular Weight:

911.659

Monoisotopic Molecular Weight:

911.157467109

InChI Key:

OTEACGAEDCIMBS-PXUUTJOASA-N

InChI:

InChI=1S/C27H44N7O20P3S/c1-27(2,22(41)25(42)30-6-5-16(36)29-7-8-58-18(39)9-14(35)3-4-17(37)38)11-51-57(48,49)54-56(46,47)50-10-15-21(53-55(43,44)45)20(40)26(52-15)34-13-33-19-23(28)31-12-32-24(19)34/h12-15,20-22,26,35,40-41H,3-11H2,1-2H3,(H,29,36)(H,30,42)(H,37,38)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,15+,20+,21+,22?,26+/m0/s1

CAS number:

Not Available

IUPAC Name:

(4S)-6-({2-[(3-{[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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-hydroxy-6-oxohexanoic acid

Traditional IUPAC Name:

(3S)-3-hydroxyadipyl-coa

SMILES:

[H][C@](O)(CCC(O)=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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 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

3-hydroxyacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside 3',5'-bisphosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Medium-chain hydroxy acid
Imidazopyrimidine
Medium-chain fatty acid
Monoalkyl phosphate
Thia fatty acid
Aminopyrimidine
Fatty acid
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Saccharide
Heteroaromatic compound
Oxolane
Imidazole
Azole
Thiocarboxylic acid ester
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.53 mg/mL	ALOGPS
logP	-0.6	ALOGPS
logP	-4.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.84	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	428.14 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	194.86 m³·mol^-1	ChemAxon
Polarizability	81.26 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:

5-Carboxy-2-pentenoyl-CoA + Water <> (3S)-3-Hydroxyadipyl-CoA
(3S)-3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + NADH + 3-Oxoadipyl-CoA

Pathways:

Caprolactam degradation pae00930
Microbial metabolism in diverse environments pae01120
Phenylalanine metabolism pae00360

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0891000250-95ee831c392fd0e68f20	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0971100000-0cadf845dd290ebf5179	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2950000000-7709eb6393c101778ef8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0563-3911030342-c89e5aeeea16cfa04985	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3910120010-0539537acd3c7a9cb785	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-4dceb9b2f8705d7c11fe	View in MoNA

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	Not Available
HMDB ID	HMDB12475
Pubchem Compound ID	5282343
Kegg ID	C14145
ChemSpider ID	4445510
Wikipedia ID	Not Available
BioCyc ID	Not Available

(3S)-3-Hydroxyadipyl-CoA (PAMDB000859)

Structure for (3S)-3-Hydroxyadipyl-CoA (PAMDB000859)