NP-MRD: Showing NP-Card for 2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid (NP0244079)

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Record Information

Version

2.0

Created at

2022-09-07 04:46:49 UTC

Updated at

2022-09-07 04:46:49 UTC

NP-MRD ID

NP0244079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid

Description

2-[(2-Amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 2-[(2-Amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    5.0133   -0.1044    1.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0489    0.5020    0.3826 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2604    0.0621   -0.9931 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6310    0.2914    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899    0.6228    1.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.2617   -0.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -0.4954    0.1603 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5849    0.2888   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323    0.0581   -0.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3463    0.3930    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216    0.4933    1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0806    0.8848    3.0060 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6296    0.2627    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7022   -0.3080    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    0.6880   -1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9274    0.8716   -1.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0644   -1.9496    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -2.7557   -0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256   -2.5731    0.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -1.0465    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    0.6049    1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4938   -0.2918    2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    1.6186    0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7694    0.7597   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2927    0.1092   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -0.5305   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679   -0.1329    1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    0.0696   -1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324    1.3631   -0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432   -0.9925   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946    0.5604    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9717    1.6144   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013   -0.0922   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6470    1.9203   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.5782   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -3.0827    1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
  7 17  1  0
 17 19  1  0
 17 18  2  0
 10  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  1
  8 28  1  0
  8 29  1  0
  9 30  1  1
 16 34  1  0
 16 35  1  0
 15 32  1  0
 15 33  1  0
 10 31  1  0
 19 36  1  0
M  END


  Mrv1533004201502462D          

 19 19  0  0  0  0            999 V2000
    1.7309   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -2.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -2.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184   -2.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -4.4270    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(N)C(=O)NC(CC1CCC(=O)C(Cl)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17ClN2O4/c1-6(14)11(17)15-9(12(18)19)5-7-2-3-10(16)8(13)4-7/h4,6-7,9H,2-3,5,14H2,1H3,(H,15,17)(H,18,19)

> <INCHI_KEY>
IHGHMCQJNXVBNO-UHFFFAOYSA-N

> <FORMULA>
C12H17ClN2O4

> <MOLECULAR_WEIGHT>
288.73

> <EXACT_MASS>
288.0876847

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.95794282991817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-aminopropanamido)-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-2.0482645881410573

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.238256016164375

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5545513601361134

> <JCHEM_PKA_STRONGEST_BASIC>
8.188600286843293

> <JCHEM_POLAR_SURFACE_AREA>
109.49

> <JCHEM_REFRACTIVITY>
69.99510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-aminopropanamido)-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.231  -8.264   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.231  -5.596   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.541  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.311  -8.264   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.311  -5.596   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.851  -5.596   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.621  -4.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.161  -4.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.931  -2.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.471  -2.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.241  -4.263   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.781  -4.263   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.471  -5.596   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931  -5.596   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      13.241  -6.930   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       8.621  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.161  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.851  -8.264   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14                                                            
CONECT   17    7   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-[(2-Amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoate	Generator

Chemical Formula

C₁₂H₁₇ClN₂O₄

Average Mass

288.7300 Da

Monoisotopic Mass

288.08768 Da

IUPAC Name

2-(2-aminopropanamido)-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid

Traditional Name

2-(2-aminopropanamido)-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(N)C(=O)NC(CC1CCC(=O)C(Cl)=C1)C(O)=O

InChI Identifier

InChI=1S/C12H17ClN2O4/c1-6(14)11(17)15-9(12(18)19)5-7-2-3-10(16)8(13)4-7/h4,6-7,9H,2-3,5,14H2,1H3,(H,15,17)(H,18,19)

InChI Key

IHGHMCQJNXVBNO-UHFFFAOYSA-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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Cyclohexenone
Alpha-haloketone
Alpha-chloroketone
Amino acid or derivatives
Carboxamide group
Ketone
Secondary carboxylic acid amide
Cyclic ketone
Amino acid
Chloroalkene
Haloalkene
Vinyl halide
Carboxylic acid
Monocarboxylic acid or derivatives
Vinyl chloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Primary amine
Amine
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	-0.99	ALOGPS
logP	-2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	8.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70 m³·mol⁻¹	ChemAxon
Polarizability	27.96 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

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

14395700

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid (NP0244079)

MOL for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

3D MOL for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

3D SDF for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

3D-SDF for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

PDB for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

3D PDB for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

SMILES for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

INCHI for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

Structure for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)

3D Structure for NP0244079 (2-[(2-amino-1-hydroxypropylidene)amino]-3-(3-chloro-4-oxocyclohex-2-en-1-yl)propanoic acid)