NP-MRD: Showing NP-Card for 4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate (NP0195403)

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Record Information

Version

2.0

Created at

2022-09-04 13:15:31 UTC

Updated at

2022-09-04 13:15:31 UTC

NP-MRD ID

NP0195403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate

Description

4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Based on a literature review very few articles have been published on 4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042215152D          

 21 22  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
  2 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
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O\C=C/C1=CC=C(OC(=O)C2=C\C(=N\O)C(=O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11NO5/c17-8-7-10-1-4-12(5-2-10)21-15(19)11-3-6-14(18)13(9-11)16-20/h1-9,17,20H/b8-7-,16-13-

> <INCHI_KEY>
DCPTZVBMLLOCKP-BDKHBZMCSA-N

> <FORMULA>
C15H11NO5

> <MOLECULAR_WEIGHT>
285.255

> <EXACT_MASS>
285.063722458

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.39056211639691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate

> <JCHEM_LOGP>
2.9565013383333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.780540521241905

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.10585031923471

> <JCHEM_PKA_STRONGEST_BASIC>
-6.025958167381835

> <JCHEM_POLAR_SURFACE_AREA>
96.19

> <JCHEM_REFRACTIVITY>
77.2106

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11    4                                                       
CONECT   13    2   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
4-[(Z)-2-Hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylic acid	Generator

Chemical Formula

C₁₅H₁₁NO₅

Average Mass

285.2550 Da

Monoisotopic Mass

285.06372 Da

IUPAC Name

4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate

Traditional Name

4-[(Z)-2-hydroxyethenyl]phenyl (3Z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate

CAS Registry Number

Not Available

SMILES

O\C=C/C1=CC=C(OC(=O)C2=C\C(=N\O)C(=O)C=C2)C=C1

InChI Identifier

InChI=1S/C15H11NO5/c17-8-7-10-1-4-12(5-2-10)21-15(19)11-3-6-14(18)13(9-11)16-20/h1-9,17,20H/b8-7-,16-13-

InChI Key

DCPTZVBMLLOCKP-BDKHBZMCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Styrene
Monocyclic benzene moiety
Ketoxime
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxime
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.96	ChemAxon
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.21 m³·mol⁻¹	ChemAxon
Polarizability	28.39 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59702788

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate (NP0195403)

MOL for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

3D MOL for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

3D SDF for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

3D-SDF for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

PDB for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

3D PDB for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

SMILES for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

INCHI for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

Structure for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)

3D Structure for NP0195403 (4-[(1z)-2-hydroxyethenyl]phenyl (3z)-3-(hydroxyimino)-4-oxocyclohexa-1,5-diene-1-carboxylate)