NP-MRD: Showing NP-Card for (9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate (NP0228613)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 08:20:12 UTC

Updated at

2022-09-06 08:20:12 UTC

NP-MRD ID

NP0228613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate

Description

N1999A2 belongs to the class of organic compounds known as naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. (9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate was first documented in 2003 (PMID: 12788070). Based on a literature review a small amount of articles have been published on N1999A2 (PMID: 17105291) (PMID: 15548073).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210202D          

 36 40  0  0  0  0            999 V2000
   -2.6324   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -3.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -3.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -3.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -3.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -2.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -2.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -1.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870   -0.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190    0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    1.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    2.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435    2.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4065    2.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -0.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3689   -3.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -5.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -5.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -6.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -6.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -5.4984    0.0000 Cl  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  2  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  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  3  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
  6 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -5.5699    3.4572   -1.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3553    2.3147   -1.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678    1.0086   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5511    0.7617   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296   -0.5046   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -0.6812   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7611    0.3967   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737    1.6124   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4448    0.0642    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    1.0438    0.5185 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6421    0.8117   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8025    0.9343    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1074    0.8226   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723    0.7709   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5856    0.7695   -0.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1076   -0.3140    0.5795 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1443   -1.2556    0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3180   -0.8983   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8999   -1.9170    0.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5943    1.6055   -0.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7334    2.2739    0.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6809    2.1209    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7707    1.9700    1.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706    1.7656    2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    1.2678    1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1827    0.9087    1.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -2.0071   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -2.1919    0.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878   -3.0771   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4052   -2.8285   -0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275   -1.5709   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2350   -1.3537   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319   -2.3945   -1.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8238   -3.6703   -1.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7179   -0.0345   -1.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4098    0.2016   -1.7611 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    3.3693   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528    3.8390   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0351    4.2782   -1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9228    1.6049   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0996    2.0665    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373    0.5689   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4291    0.2441    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4768   -1.2234    0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0213   -1.3100   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0903   -0.1337   -0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3351   -2.5600   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2888    3.0692   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    1.9878    3.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -0.1039    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    1.6813    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5862   -3.1386    0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -4.0722   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9965   -3.7085   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1668   -2.1931   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6644   -2.2335   -2.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3414   -4.2153   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 35  2  0
 35 36  1  0
 35 32  1  0
 32 33  1  0
 33 34  1  0
 32 31  2  0
 31 30  1  0
 30 29  2  0
 29 27  1  0
 27 28  1  0
 27  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 26  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  3  0
 22 21  1  0
 21 20  1  0
 20 15  1  0
 15 14  1  1
 14 13  3  0
 13 12  1  0
 12 11  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 31  1  0
 11 10  1  0
 12 25  1  0
 15 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 33 55  1  0
 33 56  1  0
 34 57  1  0
 30 54  1  0
 29 53  1  0
 28 52  1  0
 10 41  1  1
 26 50  1  0
 26 51  1  0
 24 49  1  0
 21 48  1  6
 11 42  1  0
 16 43  1  1
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
  4 40  1  0
M  END


  Mrv1652309062210202D          

 36 40  0  0  0  0            999 V2000
   -2.6324   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -3.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -3.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -3.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -3.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -2.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -2.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -1.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870   -0.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190    0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5497    1.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    1.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682    2.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435    2.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4065    2.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6380   -0.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3689   -3.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -5.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -5.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -6.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -6.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034   -5.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -5.4984    0.0000 Cl  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  2  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  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  3  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
  6 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(CO)=C2C=CC(O)=C(C(=O)OC3C\C4=C\C#CC5OC5(C#CC4=C3)C(O)CO)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H21ClO8/c1-34-21-11-18-17(19(12-29)25(21)28)5-6-20(31)24(18)26(33)35-16-9-14-3-2-4-23-27(36-23,22(32)13-30)8-7-15(14)10-16/h3,5-6,10-11,16,22-23,29-32H,9,12-13H2,1H3/b14-3-

> <INCHI_KEY>
CQTJGCQVQDQRDL-BNNQUZSASA-N

> <FORMULA>
C27H21ClO8

> <MOLECULAR_WEIGHT>
508.91

> <EXACT_MASS>
508.0924953

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
51.708968727378945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0^{4,6}]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate

> <JCHEM_LOGP>
2.808905284666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73639142073786

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.500054524959225

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8803639567863817

> <JCHEM_POLAR_SURFACE_AREA>
128.98000000000002

> <JCHEM_REFRACTIVITY>
132.93759999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0^{4,6}]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate

> <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      -4.914  -7.954   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.580  -7.184   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.246  -7.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.913  -7.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.421  -7.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.755  -7.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.755  -5.644   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.088  -4.874   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.421  -4.874   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.421  -3.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.825  -2.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.349  -0.964   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.529   0.026   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.796   1.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.026   2.876   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.473   3.403   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.653   2.413   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.741   4.920   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.188   5.446   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.759   4.393   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.421   3.403   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.868   2.876   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.638   1.543   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.371   0.026   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.191  -0.964   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.667  -2.429   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.088  -7.954   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.422  -7.184   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.088  -9.494   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.755 -10.264   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.421  -9.494   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.913 -10.264   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.913 -11.804   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.246 -12.574   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.246  -9.494   0.000  0.00  0.00           C+0
HETATM   36 Cl   UNK     0      -3.580 -10.264   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20   21                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   12   26                                                  
CONECT   26   25   10                                                       
CONECT   27    6   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    5   32                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₁ClO₈

Average Mass

508.9100 Da

Monoisotopic Mass

508.09250 Da

IUPAC Name

4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0^{4,6}]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate

Traditional Name

4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0^{4,6}]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC1=C(Cl)C(CO)=C2C=CC(O)=C(C(=O)OC3C\C4=C\C#CC5OC5(C#CC4=C3)C(O)CO)C2=C1

InChI Identifier

InChI=1S/C27H21ClO8/c1-34-21-11-18-17(19(12-29)25(21)28)5-6-20(31)24(18)26(33)35-16-9-14-3-2-4-23-27(36-23,22(32)13-30)8-7-15(14)10-16/h3,5-6,10-11,16,22-23,29-32H,9,12-13H2,1H3/b14-3-

InChI Key

CQTJGCQVQDQRDL-BNNQUZSASA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxylic acids and derivatives

Alternative Parents

Substituents

1-naphthalenecarboxylic acid or derivatives
Chloronaphthalene
2-naphthol
Salicylic acid or derivatives
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Aryl chloride
Aryl halide
Ynone
Vinylogous acid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organochloride
Organohalogen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Primary alcohol
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	2.81	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.94 m³·mol⁻¹	ChemAxon
Polarizability	51.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

7982058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9806299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ji N, O'Dowd H, Rosen BM, Myers AG: Enantioselective synthesis of N1999A2. J Am Chem Soc. 2006 Nov 22;128(46):14825-7. doi: 10.1021/ja0662467. [PubMed:17105291 ]
Ji N, Rosen BM, Myers AG: Method for the rapid synthesis of highly functionalized 2-hydroxy-1-naphthoates. Syntheses of the naphthoic acid components of neocarzinostatin chromophore and N1999A2. Org Lett. 2004 Nov 25;6(24):4551-3. doi: 10.1021/ol048075l. [PubMed:15548073 ]
Miyagawa N, Sasaki D, Matsuoka M, Imanishi M, Ando T, Sugiura Y: DNA cleavage characteristics of non-protein enediyne antibiotic N1999A2. Biochem Biophys Res Commun. 2003 Jun 20;306(1):87-92. doi: 10.1016/s0006-291x(03)00925-2. [PubMed:12788070 ]
LOTUS database [Link]

Showing NP-Card for (9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate (NP0228613)

MOL for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

3D MOL for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

3D SDF for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

3D-SDF for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

PDB for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

3D PDB for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

SMILES for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

INCHI for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

Structure for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)

3D Structure for NP0228613 ((9z)-4-(1,2-dihydroxyethyl)-5-oxatricyclo[8.3.0.0⁴,⁶]trideca-1(13),9-dien-2,7-diyn-12-yl 6-chloro-2-hydroxy-5-(hydroxymethyl)-7-methoxynaphthalene-1-carboxylate)