N-acetyl-D-proline (YMDB00833)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Identification

YMDB ID

YMDB00833

Name

N-acetyl-D-proline

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-acetyl-D-proline belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acetyl-D-proline is an extremely weak basic (essentially neutral) compound (based on its pKa). N-acetyl-D-proline may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2R)-1-acetylpyrrolidine-2-carboxylic acid
1-ACETYL-D-PROLINE
1-acetyl-L-proline
1-Acetylproline
Acetylproline
L-Proline, 1-acetyl-
N-Acetyl-L-proline
Proline, 1-acetyl-, L-
(2R)-1-Acetylpyrrolidine-2-carboxylate
N-Acetylproline
N-Acetylproline, (L)-isomer

CAS number

Not Available

Weight

Average: 157.1671
Monoisotopic: 157.073893223

InChI Key

GNMSLDIYJOSUSW-ZCFIWIBFSA-N

InChI

InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m1/s1

IUPAC Name

(2R)-1-acetylpyrrolidine-2-carboxylic acid

Traditional IUPAC Name

N-acetylproline

Chemical Formula

C₇H₁₁NO₃

SMILES

CC(=O)N1CCC[C@@H]1C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Proline or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Acetamide
Carboxamide group
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidinemonocarboxylic acid (CHEBI:44272 )
N-acylpyrrolidine (CHEBI:44272 )
D-proline derivative (CHEBI:44272 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	517 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.49	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.63 m³·mol⁻¹	ChemAxon
Polarizability	15.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9300000000-defdd568f7cdb7d56525	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-47cdd30cd1badb23d793	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-096r-4900000000-4f15ca0bc330bf87b521	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3f666f354e69b72329a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0900000000-5e1bc65351b385ba7aa9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-5900000000-6e692a48a6e02ce8321d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9100000000-f8c2687cfbf901e0c795	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Zenk, M. H., Schmitt, J. H. (1965). "[Purification and properties of acetyl-CoA: D-amino acid-alpha-N-acetyltransferase from yeast]." Biochem Z 342:54-65.5847960
Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2006). "Physiological role of D-amino acid-N-acetyltransferase of Saccharomyces cerevisiae: detoxification of D-amino acids." Arch Microbiol 185:39-46.16362288

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	44272
HMDB ID	Not Available
Pubchem Compound ID	719436
Kegg ID	Not Available
ChemSpider ID	627929
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0xa93cb94c>

Enzymes

Reactions