NP-MRD: Showing NP-Card for 1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone (NP0232322)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 13:31:30 UTC

Updated at

2022-09-06 13:31:30 UTC

NP-MRD ID

NP0232322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone

Description

1,3,10,11,12,21,23-Heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]Pentacosa-5,18(25)-diene-4,7,17,24-tetrone belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone is found in Carpinus japonica. 1,3,10,11,12,21,23-Heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]Pentacosa-5,18(25)-diene-4,7,17,24-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523412D          

 36 41  0  0  0  0            999 V2000
    8.4372   -1.7377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6909   -2.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0133   -1.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2669   -1.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5433   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274    0.0965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390   -0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.1887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810   -1.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4160   -1.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068   -2.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -3.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194   -3.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602   -4.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -4.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631   -3.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -2.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962   -1.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127   -1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0591   -1.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537   -2.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -3.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693   -3.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431   -3.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497   -2.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -3.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -2.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759   -3.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8072   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6222   -2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -3.3820    0.0000 O   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  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  2  0  0  0  0
 10 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  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  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
    0.5291    1.9078   -2.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460    1.9001   -1.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610    2.3245   -0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1736    1.8988    0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3391    0.4429    0.8464 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4310    0.1596    1.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6639    0.4043    1.0942 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1285    1.6885    1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547   -0.0813   -0.3418 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9697   -0.6577   -0.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -1.1420   -0.4547 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7308   -1.9000    0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -0.3190   -0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3132   -1.1866   -0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -1.5585   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3797   -2.0482   -2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751   -1.4049   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0831   -1.8326   -1.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786   -1.7613   -1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3769   -2.0464   -1.9907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155   -1.3609    0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6301   -2.3947    0.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6354   -0.2474    0.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494    0.8884    0.0815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7369    1.9555    0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4355    1.1629   -1.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555    1.0092   -2.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    1.6152   -1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    1.3846   -0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809    0.6683    0.5399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3480   -0.8230    0.4512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6409   -1.2270    1.0928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4908   -2.3650    1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046   -0.1583    1.9488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7674    0.9304    1.0881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7897    2.0820    1.8731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.4423    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440    2.3219    0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    0.0673    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988   -0.2397    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392    2.0246    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4658    0.7267   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6888   -0.0080   -0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7452   -1.7356   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054   -2.0338    0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398    0.4437   -1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -2.2725   -2.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -3.2112    0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5788    1.8743   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9302    2.1338   -2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    0.9913    1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604   -1.2185    1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1206   -2.3134    2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6374    2.0985    2.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 29  1  0
 29 28  2  0
 28 26  1  0
 26 27  2  0
 26 24  1  0
 24 25  1  1
 24 23  1  0
 23 21  1  0
 21 22  1  1
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  2  0
 17 31  1  0
 31 30  1  0
 30 35  1  0
 35 36  1  1
 35 34  1  0
 34 32  1  0
 32 33  1  1
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
 13  5  1  0
 30 29  1  0
 35 24  1  0
 32 21  1  0
 32 31  1  0
  8 41  1  0
  7 40  1  1
  5 39  1  1
  4 37  1  0
  4 38  1  0
 28 50  1  0
 25 49  1  0
 22 48  1  0
 18 47  1  0
 31 52  1  1
 30 51  1  1
 36 54  1  0
 33 53  1  0
 13 46  1  6
 11 44  1  6
 12 45  1  0
  9 42  1  6
 10 43  1  0
M  END


  Mrv1533004191523412D          

 36 41  0  0  0  0            999 V2000
    8.4372   -1.7377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6909   -2.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0133   -1.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2669   -1.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5433   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274    0.0965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390   -0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.1887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810   -1.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4160   -1.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068   -2.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -3.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194   -3.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -3.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602   -4.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -4.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631   -3.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -2.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962   -1.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127   -1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0591   -1.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537   -2.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -3.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693   -3.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431   -3.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497   -2.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -3.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -2.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759   -3.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8072   -4.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6222   -2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -3.3820    0.0000 O   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  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  2  0  0  0  0
 10 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  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  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1OC2COC(=O)C3=CC(=O)C4(O)OC5(O)C(=O)C=C(C6C3C4(O)OC56O)C(=O)OC2C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O16/c21-7-1-4-9-10-5(2-8(22)18(29)20(10,31)36-19(9,30)17(7,28)35-18)15(26)34-13-6(3-32-14(4)25)33-16(27)12(24)11(13)23/h1-2,6,9-13,16,23-24,27-31H,3H2

> <INCHI_KEY>
PXLGMDOZNDSXDA-UHFFFAOYSA-N

> <FORMULA>
C20H18O16

> <MOLECULAR_WEIGHT>
514.348

> <EXACT_MASS>
514.0594845

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.89802707327931

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-2.169295740000001

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.33182280614224

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4410321315229417

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9449388937475325

> <JCHEM_POLAR_SURFACE_AREA>
256.03999999999996

> <JCHEM_REFRACTIVITY>
102.37480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      15.750  -3.244   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.356  -3.900   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.091  -3.022   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.698  -3.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.614  -2.105   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.347  -1.154   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.750  -1.331   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.451   0.180   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.166  -1.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.901  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.413  -1.350   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.240  -0.352   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.071  -2.948   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.643  -2.372   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.186  -4.372   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.881  -5.951   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.463  -6.552   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.499  -7.466   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.472  -8.614   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.074  -7.914   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.211  -6.774   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.859  -5.269   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.900  -3.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.437  -3.458   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.710  -1.943   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.700  -4.899   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.206  -5.710   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.543  -7.213   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.667  -6.088   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.306  -4.591   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.227  -6.037   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.570  -5.213   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.835  -6.091   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.707  -7.626   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.228  -5.435   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      15.493  -6.313   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   24                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18   27                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22    9   24                                                  
CONECT   24   23   13   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   16   22   28                                             
CONECT   28   27                                                            
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    4   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₁₆

Average Mass

514.3480 Da

Monoisotopic Mass

514.05948 Da

IUPAC Name

1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone

Traditional Name

1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone

CAS Registry Number

Not Available

SMILES

OC1OC2COC(=O)C3=CC(=O)C4(O)OC5(O)C(=O)C=C(C6C3C4(O)OC56O)C(=O)OC2C(O)C1O

InChI Identifier

InChI=1S/C20H18O16/c21-7-1-4-9-10-5(2-8(22)18(29)20(10,31)36-19(9,30)17(7,28)35-18)15(26)34-13-6(3-32-14(4)25)33-16(27)12(24)11(13)23/h1-2,6,9-13,16,23-24,27-31H,3H2

InChI Key

PXLGMDOZNDSXDA-UHFFFAOYSA-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
Carpinus japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Cyclohexenone
Oxepane
Para-dioxane
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-1.4	ALOGPS
logP	-2.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	256.04 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	102.37 m³·mol⁻¹	ChemAxon
Polarizability	42.9 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14559495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone (NP0232322)

MOL for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

3D MOL for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

3D SDF for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

3D-SDF for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

PDB for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

3D PDB for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

SMILES for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

INCHI for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

Structure for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)

3D Structure for NP0232322 (1,3,10,11,12,21,23-heptahydroxy-2,8,13,16,22-pentaoxahexacyclo[16.5.2.0³,²¹.0⁶,²⁰.0⁹,¹⁴.0¹⁹,²³]pentacosa-5,18(25)-diene-4,7,17,24-tetrone)