NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid (NP0192959)

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Record Information

Version

2.0

Created at

2022-09-04 10:16:47 UTC

Updated at

2022-09-04 10:16:47 UTC

NP-MRD ID

NP0192959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid

Description

(2S,alphaS)-BSF-A belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid is found in Botryotinia squamosa. Based on a literature review very few articles have been published on (2S,alphaS)-BSF-A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.6057    4.0888   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    2.7090   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    1.8002    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    2.2019    1.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.3499    0.4021 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4574    0.0232   -0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639   -0.6821   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.4591    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -1.9243    1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -1.4797    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -0.7815   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9162   -0.2774   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -0.4761    0.8238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389   -0.5853   -0.0018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4266   -1.4025   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7013   -0.9130    0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -0.4834    0.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -1.7472    1.7838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    4.2915    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    4.6585   -1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    4.4080    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    0.2715    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -0.5715   -1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003    1.0042   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882   -1.8409    0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -2.3189    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -1.5869    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9886   -0.6040   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458    0.1191   -2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.3849    1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5968    0.5306   -0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -2.2341   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -0.9208   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792   -1.9738   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7766   -1.8094    2.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 18  1  0
 16 17  2  0
 12  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  1
  6 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  6
 15 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
M  END


  Mrv1652309042212162D          

 18 18  0  0  1  0            999 V2000
    0.9059   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3809   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -1.9520    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](CC1=CC=CC=C1)N[C@@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H17NO4/c1-9(12(15)16)14-11(13(17)18-2)8-10-6-4-3-5-7-10/h3-7,9,11,14H,8H2,1-2H3,(H,15,16)/t9-,11-/m0/s1

> <INCHI_KEY>
RZMXVCJQDSLRSR-ONGXEEELSA-N

> <FORMULA>
C13H17NO4

> <MOLECULAR_WEIGHT>
251.282

> <EXACT_MASS>
251.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.004834848773104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid

> <JCHEM_LOGP>
0.37267620238647653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.166297151970583

> <JCHEM_PKA_STRONGEST_BASIC>
5.501641161750993

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
65.23850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid

> <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       1.691  -0.976   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.461  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.771  -0.976   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.771  -3.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -4.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.461  -4.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.691  -6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.151  -6.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.619  -4.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.151  -3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.691  -3.644   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.311  -3.644   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.081  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -0.976   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.391  -0.976   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.391  -3.644   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₇NO₄

Average Mass

251.2820 Da

Monoisotopic Mass

251.11576 Da

IUPAC Name

(2S)-2-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid

Traditional Name

(2S)-2-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](CC1=CC=CC=C1)N[C@@H](C)C(O)=O

InChI Identifier

InChI=1S/C13H17NO4/c1-9(12(15)16)14-11(13(17)18-2)8-10-6-4-3-5-7-10/h3-7,9,11,14H,8H2,1-2H3,(H,15,16)/t9-,11-/m0/s1

InChI Key

RZMXVCJQDSLRSR-ONGXEEELSA-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
Botryotinia squamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Alpha-amino acid ester
Alanine or derivatives
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Methyl ester
Carboxylic acid ester
Amino acid
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	0.37	ChemAxon
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.24 m³·mol⁻¹	ChemAxon
Polarizability	26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101652617

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid (NP0192959)

MOL for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

3D MOL for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

3D SDF for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

3D-SDF for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

PDB for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

3D PDB for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

SMILES for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

INCHI for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

Structure for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)

3D Structure for NP0192959 ((2s)-2-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}propanoic acid)