NP-MRD: Showing NP-Card for 4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid (NP0286600)

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Record Information

Version

2.0

Created at

2022-09-09 15:14:29 UTC

Updated at

2022-09-09 15:14:29 UTC

NP-MRD ID

NP0286600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid

Description

4-{3-Methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]Nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Based on a literature review very few articles have been published on 4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]Nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092217142D          

 21 23  0  0  0  0            999 V2000
   -0.6674    1.3099    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
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414   -1.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2088   -1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226   -2.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -1.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   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
   -0.6674   -0.4849    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
  3  4  1  0  0  0  0
  4  5  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
  7 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2(NC=C(C3CCC(=CC3)C(O)=O)C2=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO5/c1-8-6-15(21-14(8)20)12(17)11(7-16-15)9-2-4-10(5-3-9)13(18)19/h4,6-7,9,16H,2-3,5H2,1H3,(H,18,19)

> <INCHI_KEY>
URLXNUFTDUXVQZ-UHFFFAOYSA-N

> <FORMULA>
C15H15NO5

> <MOLECULAR_WEIGHT>
289.287

> <EXACT_MASS>
289.095022587

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.845141452431054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid

> <JCHEM_LOGP>
2.4643440169999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.539633705122757

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.249765295055094

> <JCHEM_PKA_STRONGEST_BASIC>
-6.169657866383364

> <JCHEM_POLAR_SURFACE_AREA>
92.70000000000002

> <JCHEM_REFRACTIVITY>
73.94739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.275   2.016   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.740   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.986  -0.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.392  -0.279   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.638  -1.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.477  -2.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.723  -3.621   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.130  -2.994   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.562  -5.152   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.070  -3.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.825  -2.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.246  -0.905   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15    8                                                       
CONECT   17    7    4   18                                                  
CONECT   18   17                                                            
CONECT   19    4   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₁₅H₁₅NO₅

Average Mass

289.2870 Da

Monoisotopic Mass

289.09502 Da

IUPAC Name

4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid

Traditional Name

4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC2(NC=C(C3CCC(=CC3)C(O)=O)C2=O)OC1=O

InChI Identifier

InChI=1S/C15H15NO5/c1-8-6-15(21-14(8)20)12(17)11(7-16-15)9-2-4-10(5-3-9)13(18)19/h4,6-7,9,16H,2-3,5H2,1H3,(H,18,19)

InChI Key

URLXNUFTDUXVQZ-UHFFFAOYSA-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 alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Ketone
Lactone
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Oxacycle
Enamine
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Amine
Organonitrogen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.46	ChemAxon
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.95 m³·mol⁻¹	ChemAxon
Polarizability	28.85 Å³	ChemAxon
Number of Rings	3	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

162877284

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid (NP0286600)

MOL for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

3D MOL for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

3D SDF for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

3D-SDF for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

PDB for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

3D PDB for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

SMILES for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

INCHI for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

Structure for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)

3D Structure for NP0286600 (4-{3-methyl-2,9-dioxo-1-oxa-6-azaspiro[4.4]nona-3,7-dien-8-yl}cyclohex-1-ene-1-carboxylic acid)