NP-MRD: Showing NP-Card for n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid (NP0202970)

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Record Information

Version

2.0

Created at

2022-09-04 22:19:22 UTC

Updated at

2022-09-04 22:19:22 UTC

NP-MRD ID

NP0202970

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid

Description

5-Hydroxy-3-[(methoxy-carbonyl)amino]-5-vinyl-2-cyclopenten-1-one belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Based on a literature review very few articles have been published on 5-hydroxy-3-[(methoxy-carbonyl)amino]-5-vinyl-2-cyclopenten-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200192D          

 14 14  0  0  0  0            999 V2000
    1.9268    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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  1  0  0  0  0
  3  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
 10 11  1  0  0  0  0
  6 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0202970

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(O)=NC1=CC(=O)C(O)(C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO4/c1-3-9(13)5-6(4-7(9)11)10-8(12)14-2/h3-4,13H,1,5H2,2H3,(H,10,12)

> <INCHI_KEY>
FLNBQOCZHUWGNK-UHFFFAOYSA-N

> <FORMULA>
C9H11NO4

> <MOLECULAR_WEIGHT>
197.19

> <EXACT_MASS>
197.068807838

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.03227199941401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid

> <JCHEM_LOGP>
0.6655368466666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.79875753247611

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8745545830663457

> <JCHEM_PKA_STRONGEST_BASIC>
1.4781724273026344

> <JCHEM_POLAR_SURFACE_AREA>
79.12

> <JCHEM_REFRACTIVITY>
50.8775

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.597   2.904   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.735  -1.536   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.577  -3.104   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.545  -4.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   13                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₁NO₄

Average Mass

197.1900 Da

Monoisotopic Mass

197.06881 Da

IUPAC Name

N-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid

Traditional Name

N-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid

CAS Registry Number

Not Available

SMILES

COC(O)=NC1=CC(=O)C(O)(C1)C=C

InChI Identifier

InChI=1S/C9H11NO4/c1-3-9(13)5-6(4-7(9)11)10-8(12)14-2/h3-4,13H,1,5H2,2H3,(H,10,12)

InChI Key

FLNBQOCZHUWGNK-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 acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Methylcarbamate
Vinylogous amide
Carbamic acid ester
Tertiary alcohol
Cyclic ketone
Carbonic acid derivative
Ketone
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Alcohol
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	0.67	ChemAxon
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	1.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.88 m³·mol⁻¹	ChemAxon
Polarizability	19.03 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

73020695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid (NP0202970)

MOL for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

3D MOL for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

3D SDF for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

3D-SDF for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

PDB for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

3D PDB for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

SMILES for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

INCHI for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

Structure for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)

3D Structure for NP0202970 (n-(4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl)methoxycarboximidic acid)