NP-MRD: Showing NP-Card for (2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid (NP0329801)

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Record Information

Version

2.0

Created at

2022-09-12 14:32:46 UTC

Updated at

2022-09-12 14:32:47 UTC

NP-MRD ID

NP0329801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid

Description

(S)-2-(L-gamma-Glutamylamino)-3-methylene-4-pentenoic 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. (2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid is found in Philadelphus coronarius. Based on a literature review very few articles have been published on (S)-2-(L-gamma-Glutamylamino)-3-methylene-4-pentenoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
    4.3975   -0.3730    2.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673   -0.5756    3.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804   -0.5791    2.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.7744    3.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -0.4280    1.2020 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3212    0.0438    0.9399 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    0.6366   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553    0.8067   -1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210    1.1473   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863    0.4542   -1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    0.8736   -2.1688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2728    2.2595   -2.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436    0.3894   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9896    1.1590   -0.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1272   -0.9385   -0.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857   -1.6605    0.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -2.0668   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976   -2.4387    0.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994   -0.1842    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -0.3876    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -0.7583    4.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.8322    3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -0.8814    4.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    0.4075    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.2423   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.2422   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0001    0.9857    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387    0.6710   -2.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7279   -0.6395   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    0.3047   -3.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042    2.4522   -3.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    2.8958   -1.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201   -1.6593   -1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -2.7944   -0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  5  1  0
  5 16  1  0
 16 18  1  0
 16 17  2  0
  5  3  1  0
  3  4  2  3
  3  2  1  0
  2  1  2  3
 11 13  1  0
 13 15  1  0
 13 14  2  0
 12 31  1  0
 12 32  1  0
 11 30  1  6
 10 28  1  0
 10 29  1  0
  9 26  1  0
  9 27  1  0
  8 25  1  0
  5 24  1  6
 18 34  1  0
  4 22  1  0
  4 23  1  0
  2 21  1  0
  1 19  1  0
  1 20  1  0
 15 33  1  0
M  END


  Mrv1652309122216322D          

 18 17  0  0  1  0            999 V2000
    3.8230    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809    5.8559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9664    6.2684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    7.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099    5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    1.3184    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329801

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h3,7,9H,1-2,4-5,12H2,(H,13,14)(H,15,16)(H,17,18)/t7-,9-/m0/s1

> <INCHI_KEY>
OYFFZHHPKZICIV-CBAPKCEASA-N

> <FORMULA>
C11H16N2O5

> <MOLECULAR_WEIGHT>
256.258

> <EXACT_MASS>
256.105921623

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.74152342354313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid

> <JCHEM_LOGP>
-2.227379814026727

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.926145796619878

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.925936320676945

> <JCHEM_PKA_STRONGEST_BASIC>
9.536164541334598

> <JCHEM_POLAR_SURFACE_AREA>
133.21

> <JCHEM_REFRACTIVITY>
62.44800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.136   1.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470   2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.136   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.804   6.311   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.137   7.081   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.471   6.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.137   8.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.471   9.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.471  10.931   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.137  11.701   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      13.805  11.701   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.805  13.241   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      15.138  10.931   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.137   4.001   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.471   4.771   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.137   2.461   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   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(S)-2-(L-g-Glutamylamino)-3-methylene-4-pentenoate	Generator
(S)-2-(L-g-Glutamylamino)-3-methylene-4-pentenoic acid	Generator
(S)-2-(L-gamma-Glutamylamino)-3-methylene-4-pentenoate	Generator
(S)-2-(L-Γ-glutamylamino)-3-methylene-4-pentenoate	Generator
(S)-2-(L-Γ-glutamylamino)-3-methylene-4-pentenoic acid	Generator

Chemical Formula

C₁₁H₁₆N₂O₅

Average Mass

256.2580 Da

Monoisotopic Mass

256.10592 Da

IUPAC Name

(2S)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid

Traditional Name

(2S)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(O)=N[C@H](C(O)=O)C(=C)C=C)C(O)=O

InChI Identifier

InChI=1S/C11H16N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h3,7,9H,1-2,4-5,12H2,(H,13,14)(H,15,16)(H,17,18)/t7-,9-/m0/s1

InChI Key

OYFFZHHPKZICIV-CBAPKCEASA-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
Philadelphus coronarius	LOTUS Database	35616633

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
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Branched fatty acid
N-acyl-amine
Fatty acyl
Fatty amide
Dicarboxylic acid or derivatives
Fatty acid
Unsaturated fatty acid
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Organic nitrogen compound
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-2.2	ChemAxon
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	62.45 m³·mol⁻¹	ChemAxon
Polarizability	24.74 Å³	ChemAxon
Number of Rings	0	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

24796865

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-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid (NP0329801)

MOL for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

3D MOL for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

3D SDF for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

3D-SDF for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

PDB for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

3D PDB for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

SMILES for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

INCHI for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

Structure for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)

3D Structure for NP0329801 ((2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-methylidenepent-4-enoic acid)