NP-MRD: Showing NP-Card for 2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one (NP0085192)

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Record Information

Version

2.0

Created at

2022-04-29 05:47:00 UTC

Updated at

2022-04-29 05:47:00 UTC

NP-MRD ID

NP0085192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one

Description

Avenalumin II belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom). 2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one is found in Avena sativa and Puccinia coronata. Based on a literature review very few articles have been published on Avenalumin II.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.7370    1.5499    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3370    1.7719    0.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4007    0.8337    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8552   -0.3281   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9523   -1.2768   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6025   -1.0276   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    0.1100    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.3788    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2142   -0.4817   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6568   -0.2252    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.0977   -0.2092 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.8831   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -1.7861   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2269   -1.5523   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861   -0.3692    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715    0.5736    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    0.2854    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250    1.1643    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    2.2294    1.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607    0.8784    0.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677    1.0502    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8965    1.4737   -0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3336    2.3598    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0234    0.5687    1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9233   -0.4419   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -2.1727   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.7929   -0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    1.2941    0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.4107   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482   -2.6940   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9552   -2.2818   -0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6438   -0.1375    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9651    1.4944    1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    1.9430    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  7 21  2  0
 21  3  1  0
 20 10  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 21 34  1  0
M  END


  Mrv1652304292207472D          

 21 23  0  0  0  0            999 V2000
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   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
   -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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  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
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC(\C=C\C2=NC3=CC=CC=C3C(=O)O2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO3/c1-20-13-6-4-5-12(11-13)9-10-16-18-15-8-3-2-7-14(15)17(19)21-16/h2-11H,1H3/b10-9+

> <INCHI_KEY>
NODJLUIXDICTEH-MDZDMXLPSA-N

> <FORMULA>
C17H13NO3

> <MOLECULAR_WEIGHT>
279.295

> <EXACT_MASS>
279.089543283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.872585657031184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(E)-2-(3-methoxyphenyl)ethenyl]-4H-3,1-benzoxazin-4-one

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.7043618139999994

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.8458915165507224

> <JCHEM_POLAR_SURFACE_AREA>
47.89

> <JCHEM_REFRACTIVITY>
82.3195

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(E)-2-(3-methoxyphenyl)ethenyl]-3,1-benzoxazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   19                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19                                                            
CONECT   21    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃NO₃

Average Mass

279.2950 Da

Monoisotopic Mass

279.08954 Da

IUPAC Name

2-[(E)-2-(3-methoxyphenyl)ethenyl]-4H-3,1-benzoxazin-4-one

Traditional Name

2-[(E)-2-(3-methoxyphenyl)ethenyl]-3,1-benzoxazin-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=CC(\C=C\C2=NC3=CC=CC=C3C(=O)O2)=C1

InChI Identifier

InChI=1S/C17H13NO3/c1-20-13-6-4-5-12(11-13)9-10-16-18-15-8-3-2-7-14(15)17(19)21-16/h2-11H,1H3/b10-9+

InChI Key

NODJLUIXDICTEH-MDZDMXLPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Avena sativa L.	Plant	KNApSAcK
Puccinia coronata	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Not Available

Direct Parent

Benzoxazines

Alternative Parents

Substituents

Benzoxazine
Phenoxy compound
Anisole
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Lactone
Ether
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.57	ALOGPS
logP	3.7	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	0.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.32 m³·mol⁻¹	ChemAxon
Polarizability	29.87 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

C00054950

Chemspider ID

4944863

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440605

PDB ID

Not Available

ChEBI ID

173978

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one (NP0085192)

MOL for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

3D MOL for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

3D SDF for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

3D-SDF for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

PDB for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

3D PDB for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

SMILES for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

INCHI for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

Structure for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)

3D Structure for NP0085192 (2-(3-Methoxycinnamoyl)-4H-3,1-benzoxazin-4-one)