NP-MRD: Showing NP-Card for (2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid (NP0303696)

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Record Information

Version

2.0

Created at

2022-09-10 18:16:24 UTC

Updated at

2022-09-10 18:16:24 UTC

NP-MRD ID

NP0303696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

Description

Anticapsin 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. (2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid was first documented in 2014 (PMID: 24702628). Based on a literature review a small amount of articles have been published on Anticapsin (PMID: 35901454) (PMID: 31989543) (PMID: 29700621) (PMID: 25644640).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220162D          

 14 15  0  0  1  0            999 V2000
    1.1908    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6197    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3342    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9053    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  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
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
  4 11  1  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](C[C@H]1CCC(=O)[C@@H]2O[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO4/c10-5(9(12)13)3-4-1-2-6(11)8-7(4)14-8/h4-5,7-8H,1-3,10H2,(H,12,13)/t4-,5+,7-,8+/m1/s1

> <INCHI_KEY>
KHVZXXWDPSCGEK-ROHCDXGRSA-N

> <FORMULA>
C9H13NO4

> <MOLECULAR_WEIGHT>
199.206

> <EXACT_MASS>
199.084457903

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.309226277936222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

> <JCHEM_LOGP>
-2.602634211196056

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.97006154522898

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.969045355472093

> <JCHEM_PKA_STRONGEST_BASIC>
9.315469285510938

> <JCHEM_POLAR_SURFACE_AREA>
92.92

> <JCHEM_REFRACTIVITY>
46.0797

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  N   UNK     0       2.223   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.556   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.890   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.890   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.224   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.224   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.890  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.890  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.556   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.223   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.556   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.556   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.223   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.890   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4    9                                                  
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₃NO₄

Average Mass

199.2060 Da

Monoisotopic Mass

199.08446 Da

IUPAC Name

(2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

Traditional Name

(2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](C[C@H]1CCC(=O)[C@@H]2O[C@H]12)C(O)=O

InChI Identifier

InChI=1S/C9H13NO4/c10-5(9(12)13)3-4-1-2-6(11)8-7(4)14-8/h4-5,7-8H,1-3,10H2,(H,12,13)/t4-,5+,7-,8+/m1/s1

InChI Key

KHVZXXWDPSCGEK-ROHCDXGRSA-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

Not Available

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
Carbocyclic fatty acid
Oxepane
Fatty acyl
Ketone
Amino acid
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organopnictogen compound
Primary amine
Amine
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-2.6	ChemAxon
pKa (Strongest Acidic)	1.97	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.08 m³·mol⁻¹	ChemAxon
Polarizability	19.31 Å³	ChemAxon
Number of Rings	2	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

C00018799

Chemspider ID

65510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kutnu M, Islerel ET, Tuncbag N, Ozcengiz G: Comparative biological network analysis for differentially expressed proteins as a function of bacilysin biosynthesis in Bacillus subtilis. Integr Biol (Camb). 2022 Aug 3;14(5):99-110. doi: 10.1093/intbio/zyac010. [PubMed:35901454 ]
Ertekin O, Kutnu M, Taskin AA, Demir M, Karatas AY, Ozcengiz G: Analysis of a bac operon-silenced strain suggests pleiotropic effects of bacilysin in Bacillus subtilis. J Microbiol. 2020 Apr;58(4):297-313. doi: 10.1007/s12275-020-9064-0. Epub 2020 Jan 28. [PubMed:31989543 ]
Wang T, Liu XH, Wu MB, Ge S: Molecular insights into the antifungal mechanism of bacilysin. J Mol Model. 2018 Apr 26;24(5):118. doi: 10.1007/s00894-018-3645-4. [PubMed:29700621 ]
Ozcengiz G, Ogulur I: Biochemistry, genetics and regulation of bacilysin biosynthesis and its significance more than an antibiotic. N Biotechnol. 2015 Dec 25;32(6):612-9. doi: 10.1016/j.nbt.2015.01.006. Epub 2015 Jan 30. [PubMed:25644640 ]
Tsuda T, Asami M, Koguchi Y, Kojima S: Single mutation alters the substrate specificity of L-amino acid ligase. Biochemistry. 2014 Apr 29;53(16):2650-60. doi: 10.1021/bi500292b. Epub 2014 Apr 17. [PubMed:24702628 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid (NP0303696)

MOL for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

3D MOL for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

3D SDF for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

3D-SDF for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

PDB for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

3D PDB for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

SMILES for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

INCHI for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

Structure for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)

3D Structure for NP0303696 ((2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid)