NP-MRD: Showing NP-Card for 4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid (NP0263718)

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Record Information

Version

2.0

Created at

2022-09-08 06:59:15 UTC

Updated at

2022-09-08 06:59:16 UTC

NP-MRD ID

NP0263718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid

Description

Gabredin 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. 4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid is found in Streptomyces venezuelae. Based on a literature review very few articles have been published on Gabredin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -6.5942   -2.1273   -0.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -1.1039   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2259   -0.0597    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5994   -1.0386   -0.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018    0.2537   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5841    0.3603   -1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958    1.6248   -0.9872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383    1.6588   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861    2.8751    0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    0.4853    0.4357 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -0.1207    0.0881 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7836    0.9040    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1494    0.4769    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    0.6669   -1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    0.2372   -1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524   -0.3844   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -0.5903    0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -0.1528    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652   -1.3744    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354   -1.7477    1.6180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -2.1767    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640    0.5263    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7695   -1.0727   -2.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.8610   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    0.3028    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    1.1451   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013    0.3151   -2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -0.4531   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005    3.3403    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230   -0.0058    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -0.2853   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    1.2287    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608    1.7991   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746    1.1621   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061    0.4080   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7636   -0.7086   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218   -1.0834    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4298   -0.3300    2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741   -3.0941    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 21  1  0
 19 20  2  0
 18 13  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
M  END


  Mrv1652309082208592D          

 21 21  0  0  1  0            999 V2000
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263718

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O5/c17-12(18)7-4-8-15-14(21)16-11(13(19)20)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,17,18)(H,19,20)(H2,15,16,21)/t11-/m0/s1

> <INCHI_KEY>
SXJDRCVQKGQHOW-NSHDSACASA-N

> <FORMULA>
C14H18N2O5

> <MOLECULAR_WEIGHT>
294.307

> <EXACT_MASS>
294.121571688

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.500846613870795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{N-[(1S)-1-carboxy-2-phenylethyl]-(C-hydroxycarbonimidoyl)amino}butanoic acid

> <JCHEM_LOGP>
-0.06933889663235791

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.838232983283453

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.635654427331793

> <JCHEM_PKA_STRONGEST_BASIC>
7.673025701806252

> <JCHEM_POLAR_SURFACE_AREA>
119.22

> <JCHEM_REFRACTIVITY>
74.1942

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{N-[(1S)-1-carboxy-2-phenylethyl]-(C-hydroxycarbonimidoyl)amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.669  -9.240   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      13.337  -9.240   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   11   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈N₂O₅

Average Mass

294.3070 Da

Monoisotopic Mass

294.12157 Da

IUPAC Name

4-{N-[(1S)-1-carboxy-2-phenylethyl]-(C-hydroxycarbonimidoyl)amino}butanoic acid

Traditional Name

4-{N-[(1S)-1-carboxy-2-phenylethyl]-(C-hydroxycarbonimidoyl)amino}butanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H18N2O5/c17-12(18)7-4-8-15-14(21)16-11(13(19)20)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,17,18)(H,19,20)(H2,15,16,21)/t11-/m0/s1

InChI Key

SXJDRCVQKGQHOW-NSHDSACASA-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
Streptomyces venezuelae	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
N-carbamoyl-alpha-amino acid or derivatives
N-carbamoyl-alpha-amino acid
Gamma amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Urea
Carbonic acid derivative
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-0.069	ChemAxon
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	7.67	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	74.19 m³·mol⁻¹	ChemAxon
Polarizability	29.5 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

102230711

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid (NP0263718)

MOL for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

3D MOL for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

3D SDF for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

3D-SDF for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

PDB for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

3D PDB for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

SMILES for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

INCHI for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

Structure for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)

3D Structure for NP0263718 (4-{n-[(1s)-1-carboxy-2-phenylethyl]-(c-hydroxycarbonimidoyl)amino}butanoic acid)