NP-MRD: Showing NP-Card for (2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid (NP0228231)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 07:48:07 UTC

Updated at

2022-09-06 07:48:07 UTC

NP-MRD ID

NP0228231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

Description

Chondrochloren A belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Chondrochloren A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid is found in Chondromyces crocatus. (2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid was first documented in 2010 (PMID: 20080978). Based on a literature review very few articles have been published on chondrochloren A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209482D          

 36 36  0  0  1  0            999 V2000
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7184   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2894   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4328   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -3.7125    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
M  END

     RDKit          3D

 76 76  0  0  0  0  0  0  0  0999 V2000
   -5.9384    3.7746   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6511    3.5468   -1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1780    2.2084   -1.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187    1.6242   -1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4300    1.4280   -0.0761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1832    2.6336    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770    0.3597    0.7172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5925    0.3662    1.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -1.0024    0.0792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9429   -1.9951    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284   -1.5511   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046   -1.6828   -1.5324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7459   -1.9700    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -1.9629    2.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884   -2.4412    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598   -2.8886    0.8687 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4397   -3.5672   -0.0166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -4.8799    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -1.8201    1.5101 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4091   -2.5110    2.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1607   -0.9655    0.5215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3663   -0.1899   -0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -0.4477   -1.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -0.1359    1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6935    0.8485    2.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376   -0.3120    1.1783 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.2746    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598   -1.0941   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3128    0.2161   -1.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842    1.4139   -0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723    2.6143   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2986    2.6801   -2.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7688    3.8877   -2.5582 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6223    1.4710   -2.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6795    1.5061   -4.0459 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1597    0.2779   -2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9798    4.2264    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9919    2.8509    0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867    4.5061    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9807    4.3750   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6251    3.7813   -2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0710    1.5086   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1546    2.1952   -2.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0963    2.2080   -1.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272    0.5990   -1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881    0.9536   -0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586    2.5718    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156    3.5797    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    2.7660    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2488    0.6034    0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068    0.9610    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7575   -0.8904   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9927   -2.0906    0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5411   -3.0024    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0859   -1.5246    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -1.0525    2.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1781   -2.7841    2.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -2.1561    2.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5473   -2.4782   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988   -3.6873    1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -5.4126    0.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317   -5.3141   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551   -4.8897    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8862   -1.2166    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859   -1.8879    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.6510   -0.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7095   -0.1899   -1.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -1.5184   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0135    0.1967   -2.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.7302    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -2.3271    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2287   -1.9619   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3567    1.4637    0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1921    3.5395   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3748    3.9171   -3.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343   -0.6631   -2.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 36 29  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  4 45  1  0
  5 46  1  6
  6 47  1  0
  6 48  1  0
  6 49  1  0
  7 50  1  1
  8 51  1  0
  9 52  1  6
 10 53  1  0
 10 54  1  0
 10 55  1  0
 14 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 16 60  1  1
 18 61  1  0
 18 62  1  0
 18 63  1  0
 19 64  1  1
 20 65  1  0
 21 66  1  6
 23 67  1  0
 23 68  1  0
 23 69  1  0
 25 70  1  0
 27 71  1  0
 28 72  1  0
 30 73  1  0
 31 74  1  0
 33 75  1  0
 36 76  1  0
M  END


  Mrv1652309062209482D          

 36 36  0  0  1  0            999 V2000
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7184   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2894   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4328   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -3.7125    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@H](C)[C@H](O)[C@H](C)C(=O)C(\C)=C\[C@@H](OC)[C@@H](O)[C@@H](OC)C(O)=N\C=C/C1=CC=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H40ClNO7/c1-7-8-9-16(2)23(31)18(4)24(32)17(3)14-22(35-5)25(33)26(36-6)27(34)29-13-12-19-10-11-21(30)20(28)15-19/h10-16,18,22-23,25-26,30-31,33H,7-9H2,1-6H3,(H,29,34)/b13-12-,17-14+/t16-,18+,22-,23+,25-,26-/m1/s1

> <INCHI_KEY>
FYBGSKAWXCBCIQ-JRAUAZSASA-N

> <FORMULA>
C27H40ClNO7

> <MOLECULAR_WEIGHT>
526.07

> <EXACT_MASS>
525.2493303

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.72470530734826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5E,8S,9S,10R)-N-[(Z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

> <JCHEM_LOGP>
2.679742239246457

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.407089156416859

> <JCHEM_PKA_STRONGEST_ACIDIC>
-6.0970355781632355

> <JCHEM_PKA_STRONGEST_BASIC>
10.852456772801808

> <JCHEM_POLAR_SURFACE_AREA>
128.81000000000003

> <JCHEM_REFRACTIVITY>
141.58560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5E,8S,9S,10R)-N-[(Z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      21.339 -13.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.673 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.006 -13.860   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.340 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.674 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.007 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      29.341 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      29.341 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.007 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      26.674  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      29.341  -9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      30.675 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      30.675 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.341  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.007  -6.930   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      30.675  -6.930   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.008  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.676  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.009  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.009  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      37.343  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      34.676  -7.700   0.000  0.00  0.00           C+0
HETATM   35 Cl   UNK     0      34.676  -9.240   0.000  0.00  0.00          Cl+0
HETATM   36  C   UNK     0      33.342  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀ClNO₇

Average Mass

526.0700 Da

Monoisotopic Mass

525.24933 Da

IUPAC Name

(2R,3R,4R,5E,8S,9S,10R)-N-[(Z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

Traditional Name

(2R,3R,4R,5E,8S,9S,10R)-N-[(Z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

CAS Registry Number

Not Available

SMILES

CCCC[C@@H](C)[C@H](O)[C@H](C)C(=O)C(\C)=C\[C@@H](OC)[C@@H](O)[C@@H](OC)C(O)=N\C=C/C1=CC=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C27H40ClNO7/c1-7-8-9-16(2)23(31)18(4)24(32)17(3)14-22(35-5)25(33)26(36-6)27(34)29-13-12-19-10-11-21(30)20(28)15-19/h10-16,18,22-23,25-26,30-31,33H,7-9H2,1-6H3,(H,29,34)/b13-12-,17-14+/t16-,18+,22-,23+,25-,26-/m1/s1

InChI Key

FYBGSKAWXCBCIQ-JRAUAZSASA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Chondromyces crocatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

2-halophenol
2-chlorophenol
Styrene
Chlorobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
B'-hydroxy-alpha,beta-unsaturated-ketone
Fatty amide
Fatty acyl
Monosaccharide
N-acyl-amine
Aryl chloride
Alpha-branched alpha,beta-unsaturated-ketone
Aryl halide
Beta-hydroxy ketone
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Secondary carboxylic acid amide
Ketone
Secondary alcohol
Carboxamide group
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Alcohol
Organic nitrogen compound
Organohalogen compound
Carbonyl group
Organochloride
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	2.68	ChemAxon
pKa (Strongest Acidic)	-6.1	ChemAxon
pKa (Strongest Basic)	10.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.81 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	141.59 m³·mol⁻¹	ChemAxon
Polarizability	56.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

9905807

KEGG Compound ID

Not Available

BioCyc ID

CPD-18432

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11731091

PDB ID

Not Available

ChEBI ID

132426

Good Scents ID

Not Available

References

General References

Rachid S, Revermann O, Dauth C, Kazmaier U, Muller R: Characterization of a novel type of oxidative decarboxylase involved in the biosynthesis of the styryl moiety of chondrochloren from an acylated tyrosine. J Biol Chem. 2010 Apr 23;285(17):12482-9. doi: 10.1074/jbc.M109.079707. Epub 2010 Jan 15. [PubMed:20080978 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid (NP0228231)

MOL for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D MOL for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D SDF for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D-SDF for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

PDB for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D PDB for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

SMILES for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

INCHI for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

Structure for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D Structure for NP0228231 ((2r,3r,4r,5e,8s,9s,10r)-n-[(1z)-2-(3-chloro-4-hydroxyphenyl)ethenyl]-3,9-dihydroxy-2,4-dimethoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)