NP-MRD: Showing NP-Card for (1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one (NP0219592)

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Record Information

Version

2.0

Created at

2022-09-05 20:38:36 UTC

Updated at

2022-09-05 20:38:36 UTC

NP-MRD ID

NP0219592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one

Description

Waltherione A belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. (1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one was first documented in 2014 (PMID: 24392742). Based on a literature review a small amount of articles have been published on Waltherione A (PMID: 32946697) (PMID: 30701660) (PMID: 28359850) (PMID: 25494674).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222382D          

 29 33  0  0  1  0            999 V2000
   -1.1717    0.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    0.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7710   -1.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226   -2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -0.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081   -0.3982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6354   -1.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9912   -0.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3319   -0.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6172    0.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    0.2813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5286    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1878    1.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4731    2.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454    3.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471    2.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765    0.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    1.3412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0309    1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    0.0522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0219    0.8633    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
  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
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  6  0  0  0
 25 29  1  6  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -3.3121   -2.7091    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.4046    0.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -0.3172   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8582   -0.5233   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6737    0.5286   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1810    1.7985   -0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9240    1.9927   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0694    0.9391    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    1.1712    0.6182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5469    2.5871    0.4704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884    0.6270   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    0.1915   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814   -0.2840   -2.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789   -0.3211   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6246   -0.8047   -2.0839 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8532   -0.8893   -1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179   -1.4232   -2.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013   -0.4553   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244   -0.4991    0.3664 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0692    0.6416    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    0.0516    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055    0.4377    1.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6928    0.1285   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964    0.6245    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248    1.0772    2.0176 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4832   -0.0626    2.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -0.4940    2.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088    0.8438    2.0560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4785    1.7556    2.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6566   -3.4753    0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644   -2.9128   -1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3114   -2.8425    0.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2113   -1.5512   -0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6597    0.3330   -1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8316    2.6152   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5779    3.0256   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495    2.7582   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6888    0.2399   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827   -0.6320   -3.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162   -1.1369   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9135   -0.8592   -1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1949   -2.4885   -2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -1.2901   -3.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1612    1.1007    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0788    0.3788   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6284    1.4205   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    1.8247    2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.9043    2.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    0.3223    3.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4103   -1.1799    2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -0.9521    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    0.9978    2.7071 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  1
  9 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 29  1  0
 25 24  1  0
 24 23  2  0
 23 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
  8  3  1  0
 11  9  1  0
 29 28  1  0
 11 24  1  0
 21 23  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 28 52  1  1
 27 50  1  0
 27 51  1  0
 26 48  1  0
 26 49  1  0
 25 47  1  6
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 13 39  1  0
 12 38  1  0
M  END


  Mrv1652309052222382D          

 29 33  0  0  1  0            999 V2000
   -1.1717    0.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    0.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7710   -1.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226   -2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -0.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081   -0.3982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6354   -1.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9912   -0.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3319   -0.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6172    0.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    0.2813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5286    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1878    1.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4731    2.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454    3.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3748    1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471    2.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765    0.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    1.3412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0309    1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169    0.0522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0219    0.8633    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
  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
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  6  0  0  0
 25 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1[C@@]1(O)[C@H]2CC[C@H](O2)C2=C3C(NC(C)=C(OC)C3=O)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C23H23NO5/c1-12-22(28-3)21(25)20-15(24-12)9-8-14-19(20)17-10-11-18(29-17)23(14,26)13-6-4-5-7-16(13)27-2/h4-9,17-18,26H,10-11H2,1-3H3,(H,24,25)/t17-,18+,23-/m0/s1

> <INCHI_KEY>
VTNKIOPLJCPQRL-IXFSTUDKSA-N

> <FORMULA>
C23H23NO5

> <MOLECULAR_WEIGHT>
393.439

> <EXACT_MASS>
393.157622845

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.672268308839364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12R,13R)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0^{2,11}.0^{3,8}]hexadeca-2,5,8,10-tetraen-4-one

> <JCHEM_LOGP>
2.8918573659999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208273681894338

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.747789138916

> <JCHEM_PKA_STRONGEST_BASIC>
-4.022274224140573

> <JCHEM_POLAR_SURFACE_AREA>
77.02

> <JCHEM_REFRACTIVITY>
111.68839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12R,13R)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0^{2,11}.0^{3,8}]hexadeca-2,5,8,10-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.187   0.526   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.706   0.103   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.332  -1.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.439  -2.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.065  -3.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.415  -4.379   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.522  -3.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.148  -1.814   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.255  -0.743   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.053  -2.061   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.717  -0.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.702  -1.442   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.220  -1.181   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.752   0.264   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.270   0.525   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       8.802   1.970   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.320   2.231   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.817   3.154   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.350   4.599   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.365   5.783   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.300   2.893   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.315   4.076   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.767   1.448   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.249   1.186   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.452   2.504   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.924   2.701   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.818   1.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.965   0.098   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.907   1.611   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11   28                                             
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23   11   25                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    9   29                                                  
CONECT   29   28   25                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Waltherione-a	MeSH

Chemical Formula

C₂₃H₂₃NO₅

Average Mass

393.4390 Da

Monoisotopic Mass

393.15762 Da

IUPAC Name

(1S,12R,13R)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0^{2,11}.0^{3,8}]hexadeca-2,5,8,10-tetraen-4-one

Traditional Name

(1S,12R,13R)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0^{2,11}.0^{3,8}]hexadeca-2,5,8,10-tetraen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1[C@@]1(O)[C@H]2CC[C@H](O2)C2=C3C(NC(C)=C(OC)C3=O)=CC=C12

InChI Identifier

InChI=1S/C23H23NO5/c1-12-22(28-3)21(25)20-15(24-12)9-8-14-19(20)17-10-11-18(29-17)23(14,26)13-6-4-5-7-16(13)27-2/h4-9,17-18,26H,10-11H2,1-3H3,(H,24,25)/t17-,18+,23-/m0/s1

InChI Key

VTNKIOPLJCPQRL-IXFSTUDKSA-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 hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
2-benzopyran
Benzopyran
Isochromane
Dihydroquinoline
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Methylpyridine
Benzenoid
Pyridine
Monocyclic benzene moiety
Oxolane
Tertiary alcohol
Vinylogous amide
Heteroaromatic compound
Oxacycle
Dialkyl ether
Ether
Azacycle
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	2.89	ChemAxon
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.02 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.69 m³·mol⁻¹	ChemAxon
Polarizability	41.67 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

C00034336

Chemspider ID

9649692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11474862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rahim A, Saito Y, Fukuyoshi S, Miyake K, Goto M, Chen CH, Alam G, Lee KH, Nakagawa-Goto K: Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata. J Nat Prod. 2020 Oct 23;83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454. Epub 2020 Sep 18. [PubMed:32946697 ]
Jang JY, Le Dang Q, Choi GJ, Park HW, Kim JC: Control of root-knot nematodes using Waltheria indica producing 4-quinolone alkaloids. Pest Manag Sci. 2019 Aug;75(8):2264-2270. doi: 10.1002/ps.5363. Epub 2019 Mar 15. [PubMed:30701660 ]
Monteillier A, Cretton S, Ciclet O, Marcourt L, Ebrahimi SN, Christen P, Cuendet M: Cancer chemopreventive activity of compounds isolated from Waltheria indica. J Ethnopharmacol. 2017 May 5;203:214-225. doi: 10.1016/j.jep.2017.03.048. Epub 2017 Mar 28. [PubMed:28359850 ]
Jang JY, Dang QL, Choi YH, Choi GJ, Jang KS, Cha B, Luu NH, Kim JC: Nematicidal activities of 4-quinolone alkaloids isolated from the aerial part of Triumfetta grandidens against Meloidogyne incognita. J Agric Food Chem. 2015 Jan 14;63(1):68-74. doi: 10.1021/jf504572h. [PubMed:25494674 ]
Jadulco RC, Pond CD, Van Wagoner RM, Koch M, Gideon OG, Matainaho TK, Piskaut P, Barrows LR: 4-Quinolone alkaloids from Melochia odorata. J Nat Prod. 2014 Jan 24;77(1):183-7. doi: 10.1021/np400847t. Epub 2014 Jan 7. [PubMed:24392742 ]
LOTUS database [Link]

Showing NP-Card for (1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one (NP0219592)

MOL for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

3D MOL for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

3D SDF for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

3D-SDF for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

PDB for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

3D PDB for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

SMILES for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

INCHI for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

Structure for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)

3D Structure for NP0219592 ((1s,12r,13r)-12-hydroxy-5-methoxy-12-(2-methoxyphenyl)-6-methyl-16-oxa-7-azatetracyclo[11.2.1.0²,¹¹.0³,⁸]hexadeca-2,5,8,10-tetraen-4-one)