NP-MRD: Showing NP-Card for 2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one (NP0149561)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 05:28:16 UTC

Updated at

2022-09-02 05:28:17 UTC

NP-MRD ID

NP0149561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

Description

6-(6-O-Ureidocarbonyl-beta-D-glucopyranosyloxy)2,5-dihydroxy-7-phenyl-1H-phenalene-1-one belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. 2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one is found in Wachendorfia thyrsiflora and Xiphidium caeruleum. Based on a literature review very few articles have been published on 6-(6-O-Ureidocarbonyl-beta-D-glucopyranosyloxy)2,5-dihydroxy-7-phenyl-1H-phenalene-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207282D          

 40 44  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   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
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 13 29  2  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 17 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    8.9580   -2.4275    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9663   -2.3877    1.2410 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2972   -1.3440    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -0.1112    0.9049 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373   -1.4255    0.6405 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836   -1.9765   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7393   -2.3793   -1.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4312   -2.0106   -0.7466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2092   -2.0395   -0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4848   -0.7495   -1.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1585   -0.9549   -1.5545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -0.1122   -0.8172 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0356   -0.3890   -1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9388    0.6943   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717    1.5685   -2.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057    1.2955   -3.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860    2.6553   -2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458    2.8873   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    2.0336   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011    2.2661    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9361    1.4104    1.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378    0.3025    1.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220    0.0331    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -1.2689    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5993   -2.1729   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917   -3.4729   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -3.8657    1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -2.9796    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -1.7058    2.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    0.8784   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6030    3.4286    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4996    3.6328    1.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3791    4.2993   -0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2053    5.4253   -0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    4.0611   -1.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -0.1962    0.6148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0459    0.6935    1.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1464    0.2412    0.8224 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7382   -0.7285    1.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526    0.3503   -0.4789 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6641    1.5735   -1.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7788    0.6249    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1964   -3.2979   -1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082   -2.3695   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -2.8400   -1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9048   -0.5795   -2.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625    0.9613   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    0.5438   -3.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    3.3287   -3.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157    1.6266    2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2999   -0.3783    2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0838   -1.9698   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1568   -4.1817   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0840   -4.8570    1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -3.3259    3.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.0275    2.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0835    5.4845   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2514    4.6942   -2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5604   -1.2173    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643    1.5248    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851    1.2374    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2283   -0.8883    2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581    0.3443   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786    1.5294   -2.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 40  1  0
 40 41  1  0
 40 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 30  2  0
 30 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 33 35  2  0
 35 18  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 18 19  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 12 36  1  0
 36 37  1  0
 36 38  1  0
 15 14  1  0
 29 24  1  0
 19 30  1  0
 19 20  1  0
 39 62  1  0
 38 61  1  1
 40 63  1  1
 41 64  1  0
 10 46  1  6
  9 44  1  0
  9 45  1  0
  7 43  1  0
  4 42  1  0
  2  1  1  0
 12 47  1  6
 22 51  1  0
 21 50  1  0
 34 57  1  0
 35 58  1  0
 17 49  1  0
 16 48  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
 36 59  1  1
 37 60  1  0
M  END


  Mrv1652309022207282D          

 40 44  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   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
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 13 29  2  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 17 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0149561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(O)=NC(O)=N)O[C@@H](OC2=C3C(=CC=C4C(=O)C(O)=CC(C=C2O)=C34)C2=CC=CC=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H24N2O11/c28-26(36)29-27(37)38-10-17-21(33)22(34)23(35)25(39-17)40-24-16(31)9-12-8-15(30)20(32)14-7-6-13(19(24)18(12)14)11-4-2-1-3-5-11/h1-9,17,21-23,25,30-31,33-35H,10H2,(H3,28,29,36,37)/t17-,21-,22+,23-,25+/m1/s1

> <INCHI_KEY>
UAZMCQYNPUKNOV-ZJHKXHAFSA-N

> <FORMULA>
C27H24N2O11

> <MOLECULAR_WEIGHT>
552.492

> <EXACT_MASS>
552.138009601

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.65674129604449

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-7-phenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({hydroxy[(C-hydroxycarbonimidoyl)imino]methoxy}methyl)oxan-2-yl]oxy}-1H-phenalen-1-one

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.5484374004868804

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.021628953474243

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0171453949791918

> <JCHEM_PKA_STRONGEST_BASIC>
2.0622148467637267

> <JCHEM_POLAR_SURFACE_AREA>
222.57999999999998

> <JCHEM_REFRACTIVITY>
148.27700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-7-phenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[hydroxy(C-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  N   UNK     0      -1.334   6.930   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -2.667   4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   22   13   18                                                  
CONECT   30   19   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   17                                                       
CONECT   35   11   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    9   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
6-(6-O-Ureidocarbonyl-b-D-glucopyranosyloxy)2,5-dihydroxy-7-phenyl-1H-phenalene-1-one	Generator
6-(6-O-Ureidocarbonyl-β-D-glucopyranosyloxy)2,5-dihydroxy-7-phenyl-1H-phenalene-1-one	Generator

Chemical Formula

C₂₇H₂₄N₂O₁₁

Average Mass

552.4920 Da

Monoisotopic Mass

552.13801 Da

IUPAC Name

2,5-dihydroxy-7-phenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({hydroxy[(C-hydroxycarbonimidoyl)imino]methoxy}methyl)oxan-2-yl]oxy}-1H-phenalen-1-one

Traditional Name

2,5-dihydroxy-7-phenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[hydroxy(C-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(O)=NC(O)=N)O[C@@H](OC2=C3C(=CC=C4C(=O)C(O)=CC(C=C2O)=C34)C2=CC=CC=C2)[C@@H]1O

InChI Identifier

InChI=1S/C27H24N2O11/c28-26(36)29-27(37)38-10-17-21(33)22(34)23(35)25(39-17)40-24-16(31)9-12-8-15(30)20(32)14-7-6-13(19(24)18(12)14)11-4-2-1-3-5-11/h1-9,17,21-23,25,30-31,33-35H,10H2,(H3,28,29,36,37)/t17-,21-,22+,23-,25+/m1/s1

InChI Key

UAZMCQYNPUKNOV-ZJHKXHAFSA-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
Wachendorfia thyrsiflora	LOTUS Database	35616633
Xiphidium caeruleum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Phenalen-1-one
Phenalen
Alkyl glycoside
Glycosyl compound
2-naphthol
O-glycosyl compound
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Carbamic acid ester
Urea
Secondary alcohol
Ketone
Enol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Aldehyde
Alcohol
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
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	1.41	ALOGPS
logP	1.55	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	2.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	222.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	148.28 m³·mol⁻¹	ChemAxon
Polarizability	52.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

9278760

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11103619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one (NP0149561)

MOL for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

3D MOL for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

3D SDF for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

3D-SDF for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

PDB for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

3D PDB for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

SMILES for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

INCHI for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

Structure for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)

3D Structure for NP0149561 (2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one)