NP-MRD: Showing NP-Card for (2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid (NP0260493)

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Record Information

Version

2.0

Created at

2022-09-08 02:40:55 UTC

Updated at

2022-09-08 02:40:55 UTC

NP-MRD ID

NP0260493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid

Description

(2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid is found in Streptomyces griseorubiginosus and Streptomyces xanthochromogenes.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    6.1008    2.0501    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6025    0.9445    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3230    0.3911   -0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757    0.4414    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8239   -0.5932   -0.6651 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6056   -0.4423   -1.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367   -0.9423   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3176   -0.1377   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402   -0.2164   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -1.0430    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.8682    1.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -1.1066    0.9125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821   -0.4786    0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627    0.7950    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.8689    0.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2929    1.0740   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856   -0.2480   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9024   -1.1986   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -2.4564   -0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -1.5992    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -1.7927    0.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720    2.8172    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7931    1.6857    1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787    2.6493    1.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.9222   -1.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645    0.5531   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3313   -1.2425   -2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335    0.5394   -1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818    0.4047   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4425   -2.8649    1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331    2.4978   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9061    1.6458    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2586    1.6910   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1168   -0.3706   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -0.3279   -0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8200   -2.1975    1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 21  5  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  6
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 20 36  1  0
M  END


  Mrv1652309082204402D          

 21 22  0  0  0  0            999 V2000
    3.2156    1.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156    0.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    0.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    0.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5975   -0.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8275   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6714   -3.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -2.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359   -3.8614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -3.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -4.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385   -5.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959   -4.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097   -3.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634   -3.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -2.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -0.8157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
  7 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260493

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(\C=C/C(O)=NC2=C(O)CCC2=O)=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C14H15NO6/c1-8(16)21-13-6-9(7-20-13)2-5-12(19)15-14-10(17)3-4-11(14)18/h2,5,7,13,17H,3-4,6H2,1H3,(H,15,19)/b5-2-

> <INCHI_KEY>
VKXPFUZQXMQEDU-DJWKRKHSSA-N

> <FORMULA>
C14H15NO6

> <MOLECULAR_WEIGHT>
293.275

> <EXACT_MASS>
293.089937207

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.848744757407093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid

> <JCHEM_LOGP>
0.12125885799999969

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.47978409206459

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.597780252679569

> <JCHEM_PKA_STRONGEST_BASIC>
0.9213826876895485

> <JCHEM_POLAR_SURFACE_AREA>
105.42

> <JCHEM_REFRACTIVITY>
74.9138

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic 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  C   UNK     0       6.002   3.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.002   1.692   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.669   0.922   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.336   0.922   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.336  -0.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.582  -1.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.106  -2.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.011  -4.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.385  -5.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.853  -5.801   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.948  -4.555   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.227  -7.208   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.695  -7.369   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.925  -8.703   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.552 -10.109   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.419  -8.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.258  -6.851   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.665  -6.224   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.985  -4.718   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.566  -2.987   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.090  -1.523   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   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21                                                       
CONECT   21   20    5                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₅NO₆

Average Mass

293.2750 Da

Monoisotopic Mass

293.08994 Da

IUPAC Name

(2Z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid

Traditional Name

(2Z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(\C=C/C(O)=NC2=C(O)CCC2=O)=CO1

InChI Identifier

InChI=1S/C14H15NO6/c1-8(16)21-13-6-9(7-20-13)2-5-12(19)15-14-10(17)3-4-11(14)18/h2,5,7,13,17H,3-4,6H2,1H3,(H,15,19)/b5-2-

InChI Key

VKXPFUZQXMQEDU-DJWKRKHSSA-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 griseorubiginosus	LOTUS Database	35616633
Streptomyces xanthochromogenes	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	0.12	ChemAxon
pKa (Strongest Acidic)	5.6	ChemAxon
pKa (Strongest Basic)	0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.91 m³·mol⁻¹	ChemAxon
Polarizability	28.85 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid (NP0260493)

MOL for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

3D MOL for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

3D SDF for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

3D-SDF for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

PDB for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

3D PDB for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

SMILES for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

INCHI for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

Structure for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)

3D Structure for NP0260493 ((2z)-3-[5-(acetyloxy)-4,5-dihydrofuran-3-yl]-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)prop-2-enimidic acid)