NP-MRD: Showing NP-Card for methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate (NP0149564)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 05:28:29 UTC

Updated at

2022-09-02 05:28:29 UTC

NP-MRD ID

NP0149564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

Description

.Delta.-Rubromycin belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. .Delta.-Rubromycin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251504452D          

 37 42  0  0  0  0            999 V2000
    2.3355   -4.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -4.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -4.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -3.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015   -4.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537   -3.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -4.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4129   -3.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2198   -3.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7720   -3.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5789   -3.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8336   -3.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4469   -3.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1612   -3.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9459   -3.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1177   -2.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589   -4.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3436   -3.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5153   -3.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9565   -4.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7847   -5.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3977   -5.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1824   -5.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0000   -5.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8283   -6.3005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3871   -4.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6024   -5.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9895   -4.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1690   -4.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2814   -4.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4745   -4.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9223   -5.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1770   -5.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -4.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632   -5.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8179   -6.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7562   -5.2996    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 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
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 17 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
  9 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
   -9.3638    2.4411   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9723    2.2271   -0.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4122    0.9723   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1399   -0.0143   -0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9675    0.7955   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071   -0.4476   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0600   -0.6169    0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383   -1.9055    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984   -2.0415    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4128   -0.9301    0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9204    0.3772    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.4075    0.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832    0.5057    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.7384    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    2.7600    0.5562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1723    1.8096    0.1480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -1.1507    0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -2.2022    0.1956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1966   -3.4359    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929   -3.4025    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -2.5629    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710   -1.4877    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -0.9645   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996    0.0674   -1.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.5088   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6306   -0.0328    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784   -1.0530    0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -1.5907    2.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.4763    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3737   -0.0266    1.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5671    1.5534    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369    2.0664   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6928    3.0957   -1.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9097    3.6473   -1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    1.6038   -1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2615    2.0685   -2.5946 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234   -1.6134   -1.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9584    2.3911    0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7435    1.7909   -1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4508    3.4963   -0.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182   -1.3262   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1774   -2.7511    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644    2.3555    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -4.3192    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -3.6709   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -3.7567    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2165   -4.1163   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -2.5645    2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755   -3.5262    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609    0.4746   -2.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303   -2.3244    2.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5127    1.9584    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6723    2.8250   -1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3228    4.3951   -1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7666    4.0251   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 17  1  0
 18 17  1  1
 18 21  1  0
 21 22  1  0
 22 27  2  0
 27 28  1  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 37  1  0
 25 35  1  0
 35 36  2  0
 35 32  1  0
 32 33  1  0
 33 34  1  0
 32 31  2  0
 31 29  1  0
 29 30  2  0
 18 19  1  0
 19 20  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16  5  1  0
 13  7  1  0
 20  9  1  0
 37 18  1  0
 23 22  1  0
 29 26  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  6 41  1  0
  8 42  1  0
 21 48  1  0
 21 49  1  0
 28 51  1  0
 24 50  1  0
 34 53  1  0
 34 54  1  0
 34 55  1  0
 31 52  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 12 43  1  0
M  END


  Mrv1533004251504452D          

 37 42  0  0  0  0            999 V2000
    2.3355   -4.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -4.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -4.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -3.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015   -4.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537   -3.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -4.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4129   -3.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2198   -3.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7720   -3.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5789   -3.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8336   -3.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4469   -3.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1612   -3.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9459   -3.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1177   -2.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589   -4.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3436   -3.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5153   -3.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9565   -4.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7847   -5.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3977   -5.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1824   -5.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0000   -5.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8283   -6.3005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3871   -4.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6024   -5.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9895   -4.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1690   -4.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2814   -4.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4745   -4.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9223   -5.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1770   -5.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154   -4.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632   -5.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8179   -6.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7562   -5.2996    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 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
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 17 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
  9 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  5 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2=CC3=C(OC4(CC5=C(O)C6=C(C=C5O4)C(=O)C(OC)=CC6=O)CC3)C(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H18O11/c1-33-16-8-14(27)19-12(20(16)28)7-15-13(21(19)29)9-26(36-15)4-3-10-5-11-6-17(24(31)34-2)35-25(32)18(11)22(30)23(10)37-26/h5-8,29-30H,3-4,9H2,1-2H3

> <INCHI_KEY>
ZKNAWNXACCOZQW-UHFFFAOYSA-N

> <FORMULA>
C26H18O11

> <MOLECULAR_WEIGHT>
506.419

> <EXACT_MASS>
506.0849114

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
50.615844794707854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.9818615463333327

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.01777528692827

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.17055729687788

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4671307290784013

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
127.66759999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.360  -8.931   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.866  -9.251   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.897  -8.107   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.421  -6.642   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.403  -8.428   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.434  -7.284   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.940  -7.604   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.971  -6.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.477  -6.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.508  -5.637   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.014  -5.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.489  -7.422   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.634  -6.392   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.968  -7.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.432  -6.687   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.753  -5.181   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      21.577  -7.718   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.041  -7.242   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      23.362  -5.736   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      24.185  -8.273   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.865  -9.779   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      25.009 -10.810   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      26.474 -10.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.400 -10.255   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      22.079 -11.761   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.256  -9.224   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.791  -9.699   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.647  -8.668   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.115  -8.829   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      15.459  -8.566   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.952  -8.245   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.922  -9.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.397 -10.854   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.415  -9.069   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.385 -10.213   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.860 -11.678   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.878  -9.892   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   26                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   14   29                                                  
CONECT   29   28   12                                                       
CONECT   30   12   31                                                       
CONECT   31   30    9   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    5                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylic acid	Generator

Chemical Formula

C₂₆H₁₈O₁₁

Average Mass

506.4190 Da

Monoisotopic Mass

506.08491 Da

IUPAC Name

methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

Traditional Name

methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=CC3=C(OC4(CC5=C(O)C6=C(C=C5O4)C(=O)C(OC)=CC6=O)CC3)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C26H18O11/c1-33-16-8-14(27)19-12(20(16)28)7-15-13(21(19)29)9-26(36-15)4-3-10-5-11-6-17(24(31)34-2)35-25(32)18(11)22(30)23(10)37-26/h5-8,29-30H,3-4,9H2,1-2H3

InChI Key

ZKNAWNXACCOZQW-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Naphthofuran
Naphthoquinone
Isocoumarin
Naphthalene
2-benzopyran
Coumaran
Quinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Ketal
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Methyl ester
Lactone
Ketone
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	2.92	ALOGPS
logP	3.98	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.17	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.67 m³·mol⁻¹	ChemAxon
Polarizability	50.62 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

5481755

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate (NP0149564)

MOL for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

3D MOL for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

3D SDF for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

3D-SDF for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

PDB for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

3D PDB for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

SMILES for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

INCHI for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

Structure for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)

3D Structure for NP0149564 (methyl 4,10'-dihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3h-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate)