NP-MRD: Showing NP-Card for (s)-acpa (NP0191070)

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Record Information

Version

2.0

Created at

2022-09-04 07:53:08 UTC

Updated at

2022-09-04 07:53:08 UTC

NP-MRD ID

NP0191070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-acpa

Description

(S)-ACPA belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (s)-acpa is found in Apis cerana. Based on a literature review very few articles have been published on (S)-ACPA.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209532D          

 15 15  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4427    2.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120    2.7532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  2  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C[C@H](N)C(O)=O)C(=NO1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2O5/c1-3-4(2-5(9)7(11)12)6(8(13)14)10-15-3/h5H,2,9H2,1H3,(H,11,12)(H,13,14)/t5-/m0/s1

> <INCHI_KEY>
JDNMYUBSFDGCSX-YFKPBYRVSA-N

> <FORMULA>
C8H10N2O5

> <MOLECULAR_WEIGHT>
214.177

> <EXACT_MASS>
214.05897143

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.24194005873405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2S)-2-amino-2-carboxyethyl]-5-methyl-1,2-oxazole-3-carboxylic acid

> <JCHEM_LOGP>
-2.66989722323726

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.725488954152867

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.549071982088332

> <JCHEM_PKA_STRONGEST_BASIC>
9.20902077489066

> <JCHEM_POLAR_SURFACE_AREA>
126.64999999999999

> <JCHEM_REFRACTIVITY>
48.592200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(S)-acpa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.826   4.188   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.756   5.139   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.580   2.602   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(S)-2-Amino-3-(3-carboxy-5-methyl-4-isoxazolyl)porionic acid	Kegg
(S)-2-Amino-3-(3-carboxy-5-methyl-4-isoxazolyl)porionate	Generator

Chemical Formula

C₈H₁₀N₂O₅

Average Mass

214.1770 Da

Monoisotopic Mass

214.05897 Da

IUPAC Name

4-[(2S)-2-amino-2-carboxyethyl]-5-methyl-1,2-oxazole-3-carboxylic acid

Traditional Name

(S)-acpa

CAS Registry Number

Not Available

SMILES

CC1=C(C[C@H](N)C(O)=O)C(=NO1)C(O)=O

InChI Identifier

InChI=1S/C8H10N2O5/c1-3-4(2-5(9)7(11)12)6(8(13)14)10-15-3/h5H,2,9H2,1H3,(H,11,12)(H,13,14)/t5-/m0/s1

InChI Key

JDNMYUBSFDGCSX-YFKPBYRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Isoxazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:34017 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.7	ChemAxon
pKa (Strongest Acidic)	1.55	ChemAxon
pKa (Strongest Basic)	9.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.59 m³·mol⁻¹	ChemAxon
Polarizability	19.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

394275

KEGG Compound ID

C13673

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

447083

PDB ID

Not Available

ChEBI ID

34017

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (s)-acpa (NP0191070)

MOL for NP0191070 ((s)-acpa)

3D MOL for NP0191070 ((s)-acpa)

3D SDF for NP0191070 ((s)-acpa)

3D-SDF for NP0191070 ((s)-acpa)

PDB for NP0191070 ((s)-acpa)

3D PDB for NP0191070 ((s)-acpa)

SMILES for NP0191070 ((s)-acpa)

INCHI for NP0191070 ((s)-acpa)

Structure for NP0191070 ((s)-acpa)

3D Structure for NP0191070 ((s)-acpa)