NP-MRD: Showing NP-Card for Armaosigenin (NP0001740)

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Record Information

Version

1.0

Created at

2020-10-07 23:29:04 UTC

Updated at

2020-11-24 22:27:35 UTC

NP-MRD ID

NP0001740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armaosigenin

Description

(2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Armaosigenin is found in Daphne feddei. Based on a literature review very few articles have been published on (2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652310082001292D          

 53 54  0  0  0  0            999 V2000
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    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END

NP0001740
     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652310082001292D          

 53 54  0  0  0  0            999 V2000
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   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   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   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -7.3145    0.0000 H   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  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  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
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 24 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 21 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])C([H])(O[H])C([H])(OC1=C(OC([H])([H])[H])C([H])=C(\C([H])=C(/[H])C([H])=O)C([H])=C1OC([H])([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O8/c1-26-16-11-14(6-7-15(16)24)20(25)19(12-23)29-21-17(27-2)9-13(5-4-8-22)10-18(21)28-3/h4-11,19-20,23-25H,12H2,1-3H3/b5-4+

> <INCHI_KEY>
DWGMCUNRIQYVFE-SNAWJCMRSA-N

> <FORMULA>
C21H24O8

> <MOLECULAR_WEIGHT>
404.415

> <EXACT_MASS>
404.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.314412056304754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
1.5070228566666675

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.442122295287117

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908705686451627

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9898435218373853

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
106.50579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001740
     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
    6.8309    0.0549    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1805   -1.2071    0.8136 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -1.2900    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608   -0.2218   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -0.2793   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2467    0.9300   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157    2.0623   -0.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    1.2047   -0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    2.3890   -1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621    1.8984   -3.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    0.2264   -1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558    0.1297   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -0.4222    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -0.9209    1.3076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8477   -1.4812    2.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9237   -0.4751    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    0.0130    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3454   -0.0233    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -0.5225    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0715   -0.5421    2.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4025   -1.0188    3.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998    0.5623   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242    0.6275   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2037    1.1825   -2.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    1.6801   -3.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -1.5006   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850   -2.6050    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2069   -2.5035    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674   -3.6256    1.1131 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7983    0.3748   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523    0.8355    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756   -0.0604    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    0.7106   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.9888   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    1.9223    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040    1.6393    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767    3.1235   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    2.8881   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    2.1848   -3.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0994   -1.9001    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -2.3134    2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.7406    3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457   -0.9177    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1800    0.3703    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9490   -0.9434    2.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.1254    1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5449    0.9528   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619    2.5719   -2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1229    0.9643   -3.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605    1.9068   -4.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -1.5884   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -3.5687    0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363   -3.5976    1.4109 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  5 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28  3  1  0
 23 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
M  END

HEADER    PROTEIN                                 08-OCT-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-20         0                                  
HETATM    1  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       5.898  -6.724   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0       8.002  -6.160   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0       7.438  -4.056   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       5.335  -7.700   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.000  -7.700   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       0.000  -4.620   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       4.001  -8.470   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       4.771 -11.344   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       1.334  -8.470   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      -1.540 -13.860   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.000 -15.400   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.540 -13.860   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      -2.667 -13.860   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      -5.335 -13.860   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0      -6.668 -10.010   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0      -8.002 -13.860   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0      -5.335  -9.240   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   46  H   UNK     0       0.000  -6.160   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.334  -5.390   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   50  H   UNK     0      -0.000 -10.780   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.667 -10.780   0.000  0.00  0.00           H+0
HETATM   52  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0       3.437 -13.654   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    3   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22   23   49                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   43                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   25   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   41                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   33   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   24   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45                                                            
CONECT   49   21   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53                                                       
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  108    0
END

COMPND    NP0001740
HETATM    1  C1  UNL     1       6.831   0.055   0.646  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.181  -1.207   0.814  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.841  -1.290   0.437  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.161  -0.222  -0.072  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.812  -0.279  -0.459  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.247   0.930  -1.004  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.916   2.062  -0.464  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.809   1.205  -0.863  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.550   2.389  -1.849  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.762   1.898  -3.109  1.00  0.00           O  
HETATM   11  O4  UNL     1      -0.101   0.226  -1.246  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.356   0.130  -0.674  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.614  -0.422   0.560  1.00  0.00           C  
HETATM   14  O5  UNL     1      -0.557  -0.921   1.308  1.00  0.00           O  
HETATM   15  C10 UNL     1      -0.848  -1.481   2.571  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.924  -0.475   1.047  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.982   0.013   0.327  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.345  -0.023   0.802  1.00  0.00           C  
HETATM   19  C14 UNL     1      -5.685  -0.522   1.969  1.00  0.00           C  
HETATM   20  C15 UNL     1      -7.071  -0.542   2.416  1.00  0.00           C  
HETATM   21  O6  UNL     1      -7.402  -1.019   3.530  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.700   0.562  -0.909  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.424   0.627  -1.414  1.00  0.00           C  
HETATM   24  O7  UNL     1      -2.204   1.183  -2.651  1.00  0.00           O  
HETATM   25  C18 UNL     1      -3.279   1.680  -3.393  1.00  0.00           C  
HETATM   26  C19 UNL     1       2.220  -1.501  -0.287  1.00  0.00           C  
HETATM   27  C20 UNL     1       2.885  -2.605   0.228  1.00  0.00           C  
HETATM   28  C21 UNL     1       4.207  -2.503   0.594  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.867  -3.626   1.113  1.00  0.00           O  
HETATM   30  H1  UNL     1       6.798   0.375  -0.417  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.352   0.835   1.251  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.876  -0.060   0.971  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.724   0.711  -0.170  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.493   0.989  -2.107  1.00  0.00           H  
HETATM   35  H6  UNL     1       2.853   1.922   0.533  1.00  0.00           H  
HETATM   36  H7  UNL     1       0.604   1.639   0.162  1.00  0.00           H  
HETATM   37  H8  UNL     1       1.377   3.123  -1.657  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.387   2.888  -1.646  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.105   2.185  -3.787  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.099  -1.900   2.968  1.00  0.00           H  
HETATM   41  H12 UNL     1      -1.573  -2.313   2.402  1.00  0.00           H  
HETATM   42  H13 UNL     1      -1.250  -0.741   3.287  1.00  0.00           H  
HETATM   43  H14 UNL     1      -3.046  -0.918   2.011  1.00  0.00           H  
HETATM   44  H15 UNL     1      -6.180   0.370   0.204  1.00  0.00           H  
HETATM   45  H16 UNL     1      -4.949  -0.943   2.655  1.00  0.00           H  
HETATM   46  H17 UNL     1      -7.833  -0.125   1.748  1.00  0.00           H  
HETATM   47  H18 UNL     1      -4.545   0.953  -1.486  1.00  0.00           H  
HETATM   48  H19 UNL     1      -3.662   2.572  -2.862  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.123   0.964  -3.480  1.00  0.00           H  
HETATM   50  H21 UNL     1      -2.960   1.907  -4.426  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.200  -1.588  -0.585  1.00  0.00           H  
HETATM   52  H23 UNL     1       2.394  -3.569   0.356  1.00  0.00           H  
HETATM   53  H24 UNL     1       5.836  -3.598   1.411  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4   28
CONECT    4    5   33
CONECT    5    6   26   26
CONECT    6    7    8   34
CONECT    7   35
CONECT    8    9   11   36
CONECT    9   10   37   38
CONECT   10   39
CONECT   11   12
CONECT   12   13   13   23
CONECT   13   14   16
CONECT   14   15
CONECT   15   40   41   42
CONECT   16   17   17   43
CONECT   17   18   22
CONECT   18   19   19   44
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   22   23   23   47
CONECT   23   24
CONECT   24   25
CONECT   25   48   49   50
CONECT   26   27   51
CONECT   27   28   28   52
CONECT   28   29
CONECT   29   53
END

NP0001740
     RDKit          3D

53 54  0  0  0  0  0  0  0  0999 V2000
    6.8309    0.0549    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1805   -1.2071    0.8136 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -1.2900    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1608   -0.2218   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -0.2793   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2467    0.9300   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157    2.0623   -0.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089    1.2047   -0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    2.3890   -1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621    1.8984   -3.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    0.2264   -1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558    0.1297   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139   -0.4222    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -0.9209    1.3076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8477   -1.4812    2.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9237   -0.4751    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    0.0130    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3454   -0.0233    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -0.5225    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0715   -0.5421    2.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4025   -1.0188    3.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998    0.5623   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242    0.6275   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2037    1.1825   -2.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2793    1.6801   -3.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -1.5006   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850   -2.6050    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2069   -2.5035    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674   -3.6256    1.1131 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7983    0.3748   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523    0.8355    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8756   -0.0604    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    0.7106   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934    0.9888   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    1.9223    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040    1.6393    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767    3.1235   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872    2.8881   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    2.1848   -3.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0994   -1.9001    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -2.3134    2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.7406    3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457   -0.9177    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1800    0.3703    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9490   -0.9434    2.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.1254    1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5449    0.9528   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6619    2.5719   -2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1229    0.9643   -3.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605    1.9068   -4.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -1.5884   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -3.5687    0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363   -3.5976    1.4109 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  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  5 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28  3  1  0
 23 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₈

Average Mass

404.4150 Da

Monoisotopic Mass

404.14712 Da

IUPAC Name

(2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal

Traditional Name

(2E)-3-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-enal

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])C([H])(O[H])C([H])(OC1=C(OC([H])([H])[H])C([H])=C(\C([H])=C(/[H])C([H])=O)C([H])=C1OC([H])([H])[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C21H24O8/c1-26-16-11-14(6-7-15(16)24)20(25)19(12-23)29-21-17(27-2)9-13(5-4-8-22)10-18(21)28-3/h4-11,19-20,23-25H,12H2,1-3H3/b5-4+

InChI Key

DWGMCUNRIQYVFE-SNAWJCMRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600Mz MHz, Methanol(Solvent-Peak), experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600Mz, Methanol(Solvent-Peak), simulated)	Rgf8b			2020-10-07	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Daphne feddei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Cinnamaldehyde
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated aldehyde
Enal
Secondary alcohol
Ether
Alcohol
Organic oxygen compound
Aldehyde
Carbonyl group
Organooxygen compound
Aromatic alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.86	ALOGPS
logP	1.51	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.51 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	2	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

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

71504499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Armaosigenin (NP0001740)

MOL for NP0001740 (Armaosigenin)

3D MOL for NP0001740 (Armaosigenin)

3D SDF for NP0001740 (Armaosigenin)

3D-SDF for NP0001740 (Armaosigenin)

PDB for NP0001740 (Armaosigenin)

3D PDB for NP0001740 (Armaosigenin)

SMILES for NP0001740 (Armaosigenin)

INCHI for NP0001740 (Armaosigenin)

Structure for NP0001740 (Armaosigenin)

3D Structure for NP0001740 (Armaosigenin)