NP-MRD: Showing NP-Card for Annuloline (NP0051342)

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Record Information

Version

2.0

Created at

2022-04-27 22:44:09 UTC

Updated at

2022-04-27 22:44:09 UTC

NP-MRD ID

NP0051342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Annuloline

Description

Annuloline belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group. Annuloline is found in Lolium multiflorum . Annuloline was first documented in 2008 (PMID: 18720988). Based on a literature review very few articles have been published on Annuloline (PMID: 26398120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    9.0645   -0.5262   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9387   -1.3841   -0.5133 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6638   -0.8548   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3866    0.4843   -0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1096    0.9667   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432    0.1058   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    0.5953   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852    1.9188   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230    1.9718    0.0362 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5138    0.6965    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.2846    0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8443    1.1922    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413    0.8454    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1735    1.8625    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    1.5374    0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9278    0.2229    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2781   -0.0816    0.4074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2076    0.9525    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0004   -0.7713    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309   -2.0772    0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -3.1162    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329   -0.4629    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.0925   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3137   -1.2435   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914   -1.7441   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9311   -1.1544   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9350    0.2529    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2585   -0.1436   -1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2110    1.1826   -0.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9018    2.0397   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193    2.7754   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1111   -0.7942    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    2.2457    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8114    2.8941    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2167    2.3441    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2126    0.5566    0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9650    1.6915    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3129    1.4935   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459   -2.9792   -0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9648   -4.1160    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379   -3.0176    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -1.3183    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -1.8997   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -2.8205   -0.4547 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 24  1  0
 24 25  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 23  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 22  2  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 19 16  2  0
 16 17  1  0
 17 18  1  0
 16 15  1  0
 15 14  2  0
 25  3  1  0
 23  7  1  0
 14 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 24 43  1  0
 25 44  1  0
  8 31  1  0
 11 32  1  0
 12 33  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 15 35  1  0
 14 34  1  0
M  END


  Mrv1652304282200442D          

 25 27  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    2.1434   -0.4125    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
    0.7145   -1.2375    0.0000 C   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
    2.0964   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468   -4.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6318   -4.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4522   -4.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372   -5.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016   -6.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811   -6.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -5.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0865   -6.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -7.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7577   -5.4882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2426   -6.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CN=C(O1)\C=C\C1=CC(OC)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO4/c1-22-16-8-6-15(7-9-16)19-13-21-20(25-19)11-5-14-4-10-17(23-2)18(12-14)24-3/h4-13H,1-3H3/b11-5+

> <INCHI_KEY>
VGJRJYYLGKAWDE-VZUCSPMQSA-N

> <FORMULA>
C20H19NO4

> <MOLECULAR_WEIGHT>
337.375

> <EXACT_MASS>
337.131408096

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.750489703652846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-5-(4-methoxyphenyl)-1,3-oxazole

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
3.5745465943333325

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.7602618618811554

> <JCHEM_POLAR_SURFACE_AREA>
53.72000000000001

> <JCHEM_REFRACTIVITY>
96.0276

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
annuloline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.913  -5.525   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.897  -6.990   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343  -8.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.874  -8.075   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.779  -9.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.311  -9.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.216 -10.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.590 -11.812   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.058 -11.973   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.153 -10.727   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.495 -13.058   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.868 -14.465   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.748 -10.245   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.653 -11.490   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22   16   23                                                       
CONECT   23   22                                                            
CONECT   24    2   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₉NO₄

Average Mass

337.3750 Da

Monoisotopic Mass

337.13141 Da

IUPAC Name

2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-5-(4-methoxyphenyl)-1,3-oxazole

Traditional Name

annuloline

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CN=C(O1)\C=C\C1=CC(OC)=C(OC)C=C1

InChI Identifier

InChI=1S/C20H19NO4/c1-22-16-8-6-15(7-9-16)19-13-21-20(25-19)11-5-14-4-10-17(23-2)18(12-14)24-3/h4-13H,1-3H3/b11-5+

InChI Key

VGJRJYYLGKAWDE-VZUCSPMQSA-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
Lolium multiflorum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Oxazoles

Direct Parent

Phenyl-1,3-oxazoles

Alternative Parents

Substituents

Phenyl-1,3-oxazole
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Styrene
Methoxybenzene
2,5-disubstituted 1,3-oxazole
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Oxacycle
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methoxybenzene (CHEBI:2745 )
Alkaloids (C10570 )

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	4.16	ALOGPS
logP	3.57	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.03 m³·mol⁻¹	ChemAxon
Polarizability	37.75 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002315

Chemspider ID

4445127

KEGG Compound ID

C10570

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Skoch K, Cisarova I, Stepnicka P: Synthesis and Catalytic Use of Gold(I) Complexes Containing a Hemilabile Phosphanylferrocene Nitrile Donor. Chemistry. 2015 Nov 2;21(45):15998-6004. doi: 10.1002/chem.201502968. Epub 2015 Sep 23. [PubMed:26398120 ]
Besselievre F, Piguel S, Mahuteau-Betzer F, Grierson DS: Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes. Org Lett. 2008 Sep 18;10(18):4029-32. doi: 10.1021/ol801512q. Epub 2008 Aug 23. [PubMed:18720988 ]

Showing NP-Card for Annuloline (NP0051342)

MOL for NP0051342 (Annuloline)

3D MOL for NP0051342 (Annuloline)

3D SDF for NP0051342 (Annuloline)

3D-SDF for NP0051342 (Annuloline)

PDB for NP0051342 (Annuloline)

3D PDB for NP0051342 (Annuloline)

SMILES for NP0051342 (Annuloline)

INCHI for NP0051342 (Annuloline)

Structure for NP0051342 (Annuloline)

3D Structure for NP0051342 (Annuloline)