NP-MRD: Showing NP-Card for (1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione (NP0198370)

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Record Information

Version

2.0

Created at

2022-09-04 16:48:39 UTC

Updated at

2022-09-04 16:48:40 UTC

NP-MRD ID

NP0198370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione

Description

Demethoxyviridin belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione is found in Hypoxylon hinnuleum. (1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione was first documented in 2005 (PMID: 16320609). Based on a literature review a small amount of articles have been published on Demethoxyviridin (PMID: 29743477) (PMID: 23685090) (PMID: 19523825) (PMID: 16464575).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218482D          

 24 28  0  0  1  0            999 V2000
    2.7152    2.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.3820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3347    1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    2.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9681    1.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608    0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    0.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5367    0.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460   -0.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199   -0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -0.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666   -0.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360    0.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282    0.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443    1.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.9581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8314    2.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912    1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3202    2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
  2 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
    1.5769   -0.6529    1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2477   -0.2514    0.3281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1594   -0.5410    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137   -1.8375    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9618   -2.1508   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -1.1136   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.2072   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223    0.4779    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806    1.8916    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055    2.8140   -0.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409    2.2162    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3286    3.3474    0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6333    3.0632    0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899    1.7011    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    1.1930    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8739    0.7178    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9458    1.0746    0.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -0.6147   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406   -0.9330   -0.5324 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1809   -2.3227   -0.5420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    1.0151   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7975    0.1162    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296   -1.1854   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -2.0517   -0.8951 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552   -1.7285    1.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -0.0119    2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224   -0.5609    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228   -2.7124    0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -3.1747   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721    3.7438    0.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -0.7166   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0413   -1.3672    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135   -0.5639   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109   -2.7182   -1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7295    1.9542    0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532    1.2771   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6988    0.0037    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7891    0.3951   -0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2 19  1  0
 19 20  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11 15  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
 15  2  1  0
  3  8  1  0
  3  2  1  0
 15 14  1  0
  6  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 19 33  1  6
 20 34  1  0
 18 31  1  0
 18 32  1  0
 13 30  1  0
 21 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
  5 29  1  0
  4 28  1  0
M  END


  Mrv1652309042218482D          

 24 28  0  0  1  0            999 V2000
    2.7152    2.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.3820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3347    1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6421    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    2.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9681    1.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608    0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    0.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5367    0.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460   -0.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199   -0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -0.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4666   -0.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360    0.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282    0.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9443    1.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.9581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8314    2.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912    1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3202    2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
  2 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0198370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12[C@H](O)CC(=O)C3=COC(=C13)C(=O)C1=C3CCC(=O)C3=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,14,22H,3,5-6H2,1H3/t14-,19+/m1/s1

> <INCHI_KEY>
SWJBYJJNDIXFSA-KUHUBIRLSA-N

> <FORMULA>
C19H14O5

> <MOLECULAR_WEIGHT>
322.316

> <EXACT_MASS>
322.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.645895075583255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,18R)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione

> <JCHEM_LOGP>
1.336755303

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.851866003130432

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.849203024711777

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1864505322706402

> <JCHEM_POLAR_SURFACE_AREA>
84.58

> <JCHEM_REFRACTIVITY>
95.8774

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,18R)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.068   4.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.700   2.580   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.225   2.797   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.799   4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.323   4.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.274   3.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.700   1.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.176   1.586   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.602   0.157   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.553  -1.055   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.077  -0.061   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.219  -1.339   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.738  -0.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.680   0.621   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.126   1.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.499   1.608   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.053   1.078   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.763   3.125   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.209   3.655   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.419   5.181   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.882   0.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.186   1.635   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.810   3.129   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.798   4.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15   19                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   11    2                                                  
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19                                                            
CONECT   21    7   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    6   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₅

Average Mass

322.3160 Da

Monoisotopic Mass

322.08412 Da

IUPAC Name

(1R,18R)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione

Traditional Name

(1R,18R)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione

CAS Registry Number

Not Available

SMILES

C[C@]12[C@H](O)CC(=O)C3=COC(=C13)C(=O)C1=C3CCC(=O)C3=CC=C21

InChI Identifier

InChI=1S/C19H14O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,14,22H,3,5-6H2,1H3/t14-,19+/m1/s1

InChI Key

SWJBYJJNDIXFSA-KUHUBIRLSA-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
Hypoxylon hinnuleum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthofuran
Indanone
Naphthalene
Indane
Aryl alkyl ketone
Aryl ketone
Heteroaromatic compound
Furan
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	1.34	ChemAxon
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.58 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	95.88 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

110762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang GQ, Chen GD, Qin SY, Hu D, Awakawa T, Li SY, Lv JM, Wang CX, Yao XS, Abe I, Gao H: Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage. Nat Commun. 2018 May 9;9(1):1838. doi: 10.1038/s41467-018-04298-2. [PubMed:29743477 ]
Zheng QC, Chen GD, Kong MZ, Li GQ, Cui JY, Li XX, Wu ZY, Guo LD, Cen YZ, Zheng YZ, Gao H: Nodulisporisteriods A and B, the first 3,4-seco-4-methyl-progesteroids from Nodulisporium sp. Steroids. 2013 Sep;78(9):896-901. doi: 10.1016/j.steroids.2013.05.007. Epub 2013 May 17. [PubMed:23685090 ]
Yuan H, Pupo MT, Blois J, Smith A, Weissleder R, Clardy J, Josephson L: A stabilized demethoxyviridin derivative inhibits PI3 kinase. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4223-7. doi: 10.1016/j.bmcl.2009.05.105. Epub 2009 May 30. [PubMed:19523825 ]
Giner JL, Kehbein KA, Cook JA, Smith MC, Vlahos CJ, Badwey JA: Synthesis of fluorescent derivatives of wortmannin and demethoxyviridin as probes for phosphatidylinositol 3-kinase. Bioorg Med Chem Lett. 2006 May 1;16(9):2518-21. doi: 10.1016/j.bmcl.2006.01.091. Epub 2006 Feb 7. [PubMed:16464575 ]
Kiran I, Ilhan S, Akar T, Tur L, Erol E: Synthesis and evaluation of demethoxyviridin derivatives as potential antimicrobials. Z Naturforsch C J Biosci. 2005 Sep-Oct;60(9-10):686-92. doi: 10.1515/znc-2005-9-1005. [PubMed:16320609 ]
LOTUS database [Link]

Showing NP-Card for (1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione (NP0198370)

MOL for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

3D MOL for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

3D SDF for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

3D-SDF for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

PDB for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

3D PDB for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

SMILES for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

INCHI for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

Structure for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)

3D Structure for NP0198370 ((1r,18r)-18-hydroxy-1-methyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2,4,9,12(19),14-pentaene-6,11,16-trione)