NP-MRD: Showing NP-Card for Siphonazole (NP0006338)

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Record Information

Version

2.0

Created at

2020-12-09 03:22:53 UTC

Updated at

2021-07-15 16:54:30 UTC

NP-MRD ID

NP0006338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Siphonazole

Provided By

NPAtlas

Description

Siphonazole belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Siphonazole is found in Herpetosiphon sp. Siphonazole was first documented in 2006 (PMID: 16671154). Based on a literature review very few articles have been published on Siphonazole.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 59 61  0  0  0  0            999 V2000
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    1.1349   -1.3674    1.9010 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118273D          

 59 61  0  0  0  0            999 V2000
   10.0657    2.3929   -2.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3911    1.2939   -2.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6345   -3.8571   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.7670    0.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869    1.3361    0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3727    2.6980    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491    3.1148   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3733    2.6272   -3.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1434    0.6204   -3.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2822    1.7435   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0663   -0.7480   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    0.5121    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4052   -1.2304    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1362   -1.3202    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702   -2.0272    2.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.8262    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9690    1.9764    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3711    2.7874    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9862    2.1428    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7217    3.4270    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5432   -0.9595   -2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3309   -1.3256   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -4.6835   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2604   -3.4648   -2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855   -4.2821   -2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590    2.7137   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    3.4157    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414    3.0610   -0.3829 H   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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33  9  2  0  0  0  0
 30 15  2  0  0  0  0
 28 20  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  2 37  1  0  0  0  0
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  5 40  1  0  0  0  0
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 31 54  1  0  0  0  0
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 31 56  1  0  0  0  0
 34 57  1  0  0  0  0
 34 58  1  0  0  0  0
 34 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(\C([H])=C(/[H])C2=NC(C(=O)C([H])([H])C3=NC(C(=O)N([H])C([H])([H])C(\[H])=C(/[H])C([H])=C([H])[H])=C(O3)C([H])([H])[H])=C(O2)C([H])([H])[H])=C([H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H25N3O6/c1-5-6-7-12-26-25(31)24-16(3)34-22(28-24)14-19(30)23-15(2)33-21(27-23)11-9-17-8-10-20(32-4)18(29)13-17/h5-11,13,29H,1,12,14H2,2-4H3,(H,26,31)/b7-6+,11-9+

> <INCHI_KEY>
PJVVMJIQCNHSKW-RXUIJTJXSA-N

> <FORMULA>
C25H25N3O6

> <MOLECULAR_WEIGHT>
463.49

> <EXACT_MASS>
463.174335537

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
51.250142540720056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-{2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}-2-oxoethyl)-5-methyl-N-[(2E)-penta-2,4-dien-1-yl]-1,3-oxazole-4-carboxamide

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.234126082666667

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.971018591564935

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.886502859606346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0845406624610887

> <JCHEM_POLAR_SURFACE_AREA>
127.69000000000001

> <JCHEM_REFRACTIVITY>
128.39150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-{2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}-2-oxoethyl)-5-methyl-N-[(2E)-penta-2,4-dien-1-yl]-1,3-oxazole-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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   -8.8723    0.9416    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1176    1.5450    0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3150    2.4934    1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6649    0.0124   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7125   -0.2747   -1.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4125   -0.6076   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -2.3965   -0.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -2.8249   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -3.8571   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.7670    0.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3727    2.6980    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491    3.1148   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3733    2.6272   -3.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2822    1.7435   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0663   -0.7480   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    0.5121    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4052   -1.2304    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1362   -1.3202    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702   -2.0272    2.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.8262    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977   -0.0488    1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758   -1.7309   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8561    0.8858    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9690    1.9764    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3711    2.7874    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9862    2.1428    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7217    3.4270    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5432   -0.9595   -2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3309   -1.3256   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -4.6835   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3855   -4.2821   -2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590    2.7137   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    3.4157    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414    3.0610   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
 11 32  1  0
 32 33  1  0
 33 34  1  0
 33  9  2  0
 30 15  2  0
 28 20  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
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 12 43  1  0
 12 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
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 25 51  1  0
 27 52  1  0
 28 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 34 57  1  0
 34 58  1  0
 34 59  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      10.066   2.393  -2.521  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391   1.294  -2.245  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.005   1.027  -0.871  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.325  -0.062  -0.530  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.942  -0.315   0.865  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.508  -0.416   1.042  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.612   0.614   0.735  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.033   1.699   0.283  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.190   0.431   0.938  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.560  -0.678   1.424  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.244  -0.457   1.452  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.135  -1.367   1.901  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.697  -2.234   0.770  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.496  -3.026   0.243  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.678  -2.140   0.286  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.641  -1.317   0.772  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.779  -1.492   0.078  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.032  -0.777   0.316  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.112  -0.979  -0.414  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.384  -0.301  -0.227  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.644   0.633   0.747  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.857   1.258   0.889  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.872   0.942   0.016  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.118   1.545   0.116  0.00  0.00           O+0
HETATM   25  C   UNK     0     -10.315   2.493   1.142  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.665   0.012  -0.979  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.713  -0.275  -1.833  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.412  -0.608  -1.095  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.522  -2.397  -0.806  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.284  -2.825  -0.734  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.635  -3.857  -1.587  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.069   0.767   0.993  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.187   1.336   0.675  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.373   2.698   0.130  0.00  0.00           C+0
HETATM   35  H   UNK     0      10.349   3.115  -1.764  0.00  0.00           H+0
HETATM   36  H   UNK     0      10.373   2.627  -3.545  0.00  0.00           H+0
HETATM   37  H   UNK     0       9.143   0.620  -3.050  0.00  0.00           H+0
HETATM   38  H   UNK     0       9.282   1.744  -0.104  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.066  -0.748  -1.317  0.00  0.00           H+0
HETATM   40  H   UNK     0       8.264   0.512   1.549  0.00  0.00           H+0
HETATM   41  H   UNK     0       8.405  -1.230   1.274  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.136  -1.320   1.423  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.570  -2.027   2.678  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.301  -0.826   2.359  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.098  -0.049   1.116  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.976  -1.731  -1.208  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.856   0.886   1.435  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.969   1.976   1.683  0.00  0.00           H+0
HETATM   49  H   UNK     0     -11.371   2.787   1.109  0.00  0.00           H+0
HETATM   50  H   UNK     0      -9.986   2.143   2.139  0.00  0.00           H+0
HETATM   51  H   UNK     0      -9.722   3.427   0.953  0.00  0.00           H+0
HETATM   52  H   UNK     0      -9.543  -0.960  -2.559  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.331  -1.326  -1.901  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.336  -4.684  -0.875  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.260  -3.465  -2.097  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.385  -4.282  -2.271  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.159   2.714  -0.647  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.654   3.416   0.923  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.441   3.061  -0.383  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6   40   41                                             
CONECT    6    5    7   42                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   43   44                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   45                                                  
CONECT   19   18   20   46                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   47                                                  
CONECT   22   21   23   48                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   49   50   51                                             
CONECT   26   23   27   28                                                  
CONECT   27   26   52                                                       
CONECT   28   26   20   53                                                  
CONECT   29   17   30                                                       
CONECT   30   29   31   15                                                  
CONECT   31   30   54   55   56                                             
CONECT   32   11   33                                                       
CONECT   33   32   34    9                                                  
CONECT   34   33   57   58   59                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    2                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   31                                                            
CONECT   55   31                                                            
CONECT   56   31                                                            
CONECT   57   34                                                            
CONECT   58   34                                                            
CONECT   59   34                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
   10.0657    2.3929   -2.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3911    1.2939   -2.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045    1.0271   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3246   -0.0624   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9420   -0.3153    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5081   -0.4156    1.0415 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121    0.6140    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334    1.6991    0.2832 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897    0.4311    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602   -0.6780    1.4237 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -0.4569    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349   -1.3674    1.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966   -2.2339    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -3.0258    0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6782   -2.1402    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412   -1.3169    0.7716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -1.4923    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7771    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1124   -0.9794   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3839   -0.3005   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6438    0.6325    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8566    1.2581    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8723    0.9416    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1176    1.5450    0.1159 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3150    2.4934    1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6649    0.0124   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7125   -0.2747   -1.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4125   -0.6076   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -2.3965   -0.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -2.8249   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -3.8571   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.7670    0.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869    1.3361    0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3727    2.6980    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491    3.1148   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3733    2.6272   -3.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1434    0.6204   -3.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2822    1.7435   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0663   -0.7480   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636    0.5121    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4052   -1.2304    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1362   -1.3202    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702   -2.0272    2.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.8262    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977   -0.0488    1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758   -1.7309   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8561    0.8858    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9690    1.9764    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3711    2.7874    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9862    2.1428    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7217    3.4270    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5432   -0.9595   -2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3309   -1.3256   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -4.6835   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2604   -3.4648   -2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855   -4.2821   -2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590    2.7137   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    3.4157    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414    3.0610   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
 11 32  1  0
 32 33  1  0
 33 34  1  0
 33  9  2  0
 30 15  2  0
 28 20  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
 12 43  1  0
 12 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 27 52  1  0
 28 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 34 57  1  0
 34 58  1  0
 34 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Siphonazole b	MeSH
Siphonazole a	MeSH
2-(2-{2-[(e)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}-2-oxoethyl)-5-methyl-N-[(2E)-penta-2,4-dien-1-yl]-1,3-oxazole-4-carboximidate	Generator

Chemical Formula

C₂₅H₂₅N₃O₆

Average Mass

463.4900 Da

Monoisotopic Mass

463.17434 Da

IUPAC Name

2-(2-{2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}-2-oxoethyl)-5-methyl-N-[(2E)-penta-2,4-dien-1-yl]-1,3-oxazole-4-carboxamide

Traditional Name

2-(2-{2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}-2-oxoethyl)-5-methyl-N-[(2E)-penta-2,4-dien-1-yl]-1,3-oxazole-4-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(\C=C\C2=NC(C(=O)CC3=NC(C(=O)NC\C=C\C=C)=C(C)O3)=C(C)O2)C=C1

InChI Identifier

InChI=1S/C25H25N3O6/c1-5-6-7-12-26-25(31)24-16(3)34-22(28-24)14-19(30)23-15(2)33-21(27-23)11-9-17-8-10-20(32-4)18(29)13-17/h5-11,13,29H,1,12,14H2,2-4H3,(H,26,31)/b7-6+,11-9+

InChI Key

PJVVMJIQCNHSKW-RXUIJTJXSA-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
Herpetosiphon sp.	NPAtlas	16671154

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
2-heteroaryl carboxamide
2,4,5-trisubstituted 1,3-oxazole
Phenoxy compound
Phenol ether
Styrene
Anisole
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Heteroaromatic compound
Azole
Oxazole
Secondary carboxylic acid amide
Ketone
Carboxamide group
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.65	ALOGPS
logP	3.23	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.69 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.39 m³·mol⁻¹	ChemAxon
Polarizability	51.25 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

NPAtlas ID

NPA009453

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17284675

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16127842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nett M, Erol O, Kehraus S, Kock M, Krick A, Eguereva E, Neu E, Konig GM: Siphonazole, an unusual metabolite from Herpetosiphon sp. Angew Chem Int Ed Engl. 2006 Jun 2;45(23):3863-7. doi: 10.1002/anie.200504525. [PubMed:16671154 ]

Showing NP-Card for Siphonazole (NP0006338)

MOL for NP0006338 (Siphonazole)

3D MOL for NP0006338 (Siphonazole)

3D SDF for NP0006338 (Siphonazole)

3D-SDF for NP0006338 (Siphonazole)

PDB for NP0006338 (Siphonazole)

3D PDB for NP0006338 (Siphonazole)

SMILES for NP0006338 (Siphonazole)

INCHI for NP0006338 (Siphonazole)

Structure for NP0006338 (Siphonazole)

3D Structure for NP0006338 (Siphonazole)