NP-MRD: Showing NP-Card for (-)-4'-O-demethyl-7-methoxyisogalbulin (NP0035686)

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Record Information

Version

2.0

Created at

2021-06-20 19:03:45 UTC

Updated at

2021-06-30 00:06:50 UTC

NP-MRD ID

NP0035686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-4'-O-demethyl-7-methoxyisogalbulin

Provided By

JEOL Database JEOL Logo

Description

(1R)-1alpha-Methoxy-2beta,3beta-dimethyl-4alpha-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (-)-4'-O-demethyl-7-methoxyisogalbulin is found in Cunninghamella echinulata. (-)-4'-O-demethyl-7-methoxyisogalbulin was first documented in 2010 (Messiano, G. B., et al.). Based on a literature review very few articles have been published on (1R)-1alpha-Methoxy-2beta,3beta-dimethyl-4alpha-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121033D          

 55 57  0  0  0  0            999 V2000
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   -2.0435   -4.4852   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5155   -0.1614   -1.1960 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121033D          

 55 57  0  0  0  0            999 V2000
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   -0.1146   -1.8823    3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615   -0.8766    3.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    3.2655    4.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0352    2.6539    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    3.9671    2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377    2.8584    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306    3.1756   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903    1.6634   -3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7947    3.1186   -2.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768    2.5804   -3.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    2.1475   -3.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    3.8487   -2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    2.5780   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    2.7361   -3.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -0.1580   -2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -0.9949   -3.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.4681   -3.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    0.5338   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821   -1.9818   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4421   -4.4516   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -6.0604   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
  8  7  2  0  0  0  0
 10 11  1  0  0  0  0
 12  9  2  0  0  0  0
 20 21  1  0  0  0  0
 16 15  2  0  0  0  0
 22 23  1  0  0  0  0
 15 12  1  0  0  0  0
  5 24  1  0  0  0  0
 16 17  1  0  0  0  0
 24 25  2  0  0  0  0
  7  6  1  0  0  0  0
 25 26  1  0  0  0  0
  6 22  1  0  0  0  0
 26  3  2  0  0  0  0
 22 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 20 17  1  0  0  0  0
 26 27  1  0  0  0  0
 16  7  1  0  0  0  0
  3  2  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
 13 14  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
  9  8  1  0  0  0  0
 18 19  1  0  0  0  0
  8 33  1  0  0  0  0
 15 40  1  0  0  0  0
  6 32  1  1  0  0  0
 22 49  1  6  0  0  0
 20 45  1  6  0  0  0
 17 41  1  1  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
  4 31  1  0  0  0  0
 27 55  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@]1([H])C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2[C@]([H])(OC([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-12-13(2)22(27-6)16-11-20(26-5)19(25-4)10-15(16)21(12)14-7-8-17(23)18(9-14)24-3/h7-13,21-23H,1-6H3/t12-,13+,21-,22-/m1/s1

> <INCHI_KEY>
HNMLAPIXDGJKHU-YQJHHNQMSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.461

> <EXACT_MASS>
372.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.44080040523814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-4-[(1R,2S,3S,4R)-4,6,7-trimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenol

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.134051331666667

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.058795705611564

> <JCHEM_PKA_STRONGEST_BASIC>
-3.965774480416177

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
104.84120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-4-[(1R,2S,3S,4R)-4,6,7-trimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2691   -3.7617   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -4.4852   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -3.7358   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8198   -2.3435   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -1.6910   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155   -0.1614   -1.1960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2363    0.4727   -0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215    0.0191    1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464    0.5562    2.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477    0.1492    3.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -1.0340    3.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    1.5874    2.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    2.0643    3.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    3.0378    3.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    2.0623    0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452    1.5276   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387    2.0983   -1.5735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6208    1.4321   -2.0359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290    2.2519   -2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    1.8779   -2.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9072    2.8048   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935    0.3747   -2.5972 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1652    0.0821   -3.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6058   -2.4611   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365   -3.8530   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2939   -4.4726   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540   -5.8409   -1.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -3.1499   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850   -4.4903   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974   -3.1536   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -1.7322   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658    0.1257   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -0.7702    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753   -1.2744    4.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -1.8823    3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615   -0.8766    3.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    3.2655    4.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0352    2.6539    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    3.9671    2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377    2.8584    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306    3.1756   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903    1.6634   -3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7947    3.1186   -2.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768    2.5804   -3.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    2.1475   -3.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    3.8487   -2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    2.5780   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    2.7361   -3.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -0.1580   -2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -0.9949   -3.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.4681   -3.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    0.5338   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821   -1.9818   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4421   -4.4516   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -6.0604   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  8  7  2  0
 10 11  1  0
 12  9  2  0
 20 21  1  0
 16 15  2  0
 22 23  1  0
 15 12  1  0
  5 24  1  0
 16 17  1  0
 24 25  2  0
  7  6  1  0
 25 26  1  0
  6 22  1  0
 26  3  2  0
 22 20  1  0
  3  4  1  0
  4  5  2  0
 20 17  1  0
 26 27  1  0
 16  7  1  0
  3  2  1  0
  6  5  1  0
  2  1  1  0
 13 14  1  0
 12 13  1  0
 17 18  1  0
  9  8  1  0
 18 19  1  0
  8 33  1  0
 15 40  1  0
  6 32  1  1
 22 49  1  6
 20 45  1  6
 17 41  1  1
 11 34  1  0
 11 35  1  0
 11 36  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
  4 31  1  0
 27 55  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.269  -3.762  -1.110  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.043  -4.485  -1.150  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.895  -3.736  -1.155  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.820  -2.344  -1.182  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.431  -1.691  -1.176  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.516  -0.161  -1.196  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.236   0.473  -0.022  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.022   0.019   1.289  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.646   0.556   2.395  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.448   0.149   3.691  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.312  -1.034   3.896  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.580   1.587   2.204  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.196   2.064   3.334  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.216   3.038   3.169  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.821   2.062   0.911  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.145   1.528  -0.204  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.439   2.098  -1.573  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.621   1.432  -2.036  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.429   2.252  -2.868  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.275   1.878  -2.562  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.907   2.805  -2.247  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.094   0.375  -2.597  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.165   0.082  -3.658  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.606  -2.461  -1.149  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.537  -3.853  -1.127  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.294  -4.473  -1.131  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.254  -5.841  -1.106  0.00  0.00           O+0
HETATM   28  H   UNK     0      -3.338  -3.150  -0.204  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.085  -4.490  -1.082  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.397  -3.154  -2.011  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.718  -1.732  -1.201  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.566   0.126  -1.038  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.756  -0.770   1.422  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.275  -1.274   4.963  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.115  -1.882   3.349  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.361  -0.877   3.627  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.625   3.265   4.158  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.035   2.654   2.551  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.810   3.967   2.756  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.538   2.858   0.735  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.631   3.176  -1.472  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.290   1.663  -3.196  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.795   3.119  -2.309  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.877   2.580  -3.753  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.627   2.147  -3.567  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.576   3.849  -2.218  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.375   2.578  -1.285  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.678   2.736  -3.021  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.810  -0.158  -2.928  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.269  -0.995  -3.825  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.146   0.468  -3.363  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.895   0.534  -4.618  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.582  -1.982  -1.146  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.442  -4.452  -1.108  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.698  -6.060  -1.114  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   26    4    2                                                  
CONECT    4    3    5   31                                                  
CONECT    5   24    4    6                                                  
CONECT    6    7   22    5   32                                             
CONECT    7    8    6   16                                                  
CONECT    8    7    9   33                                                  
CONECT    9   10   12    8                                                  
CONECT   10    9   11                                                       
CONECT   11   10   34   35   36                                             
CONECT   12    9   15   13                                                  
CONECT   13   14   12                                                       
CONECT   14   13   37   38   39                                             
CONECT   15   16   12   40                                                  
CONECT   16   15   17    7                                                  
CONECT   17   16   20   18   41                                             
CONECT   18   17   19                                                       
CONECT   19   18   42   43   44                                             
CONECT   20   21   22   17   45                                             
CONECT   21   20   46   47   48                                             
CONECT   22   23    6   20   49                                             
CONECT   23   22   50   51   52                                             
CONECT   24    5   25   53                                                  
CONECT   25   24   26   54                                                  
CONECT   26   25    3   27                                                  
CONECT   27   26   55                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2691   -3.7617   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -4.4852   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -3.7358   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8198   -2.3435   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -1.6910   -1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155   -0.1614   -1.1960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2363    0.4727   -0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215    0.0191    1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464    0.5562    2.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477    0.1492    3.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -1.0340    3.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    1.5874    2.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    2.0643    3.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    3.0378    3.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    2.0623    0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452    1.5276   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387    2.0983   -1.5735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6208    1.4321   -2.0359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290    2.2519   -2.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    1.8779   -2.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9072    2.8048   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935    0.3747   -2.5972 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1652    0.0821   -3.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6058   -2.4611   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365   -3.8530   -1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2939   -4.4726   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540   -5.8409   -1.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -3.1499   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850   -4.4903   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974   -3.1536   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -1.7322   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658    0.1257   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -0.7702    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753   -1.2744    4.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146   -1.8823    3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3615   -0.8766    3.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    3.2655    4.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0352    2.6539    2.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    3.9671    2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377    2.8584    0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306    3.1756   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903    1.6634   -3.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7947    3.1186   -2.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8768    2.5804   -3.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    2.1475   -3.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    3.8487   -2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    2.5780   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    2.7361   -3.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -0.1580   -2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687   -0.9949   -3.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.4681   -3.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    0.5338   -4.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821   -1.9818   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4421   -4.4516   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -6.0604   -1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  8  7  2  0
 10 11  1  0
 12  9  2  0
 20 21  1  0
 16 15  2  0
 22 23  1  0
 15 12  1  0
  5 24  1  0
 16 17  1  0
 24 25  2  0
  7  6  1  0
 25 26  1  0
  6 22  1  0
 26  3  2  0
 22 20  1  0
  3  4  1  0
  4  5  2  0
 20 17  1  0
 26 27  1  0
 16  7  1  0
  3  2  1  0
  6  5  1  0
  2  1  1  0
 13 14  1  0
 12 13  1  0
 17 18  1  0
  9  8  1  0
 18 19  1  0
  8 33  1  0
 15 40  1  0
  6 32  1  1
 22 49  1  6
 20 45  1  6
 17 41  1  1
 11 34  1  0
 11 35  1  0
 11 36  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
  4 31  1  0
 27 55  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1R)-1a-Methoxy-2b,3b-dimethyl-4a-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin	Generator
(1R)-1Α-methoxy-2β,3β-dimethyl-4α-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4610 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

2-methoxy-4-[(1R,2S,3S,4R)-4,6,7-trimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenol

Traditional Name

2-methoxy-4-[(1R,2S,3S,4R)-4,6,7-trimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1[H])[C@]1([H])C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2[C@]([H])(OC([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H28O5/c1-12-13(2)22(27-6)16-11-20(26-5)19(25-4)10-15(16)21(12)14-7-8-17(23)18(9-14)24-3/h7-13,21-23H,1-6H3/t12-,13+,21-,22-/m1/s1

InChI Key

HNMLAPIXDGJKHU-YQJHHNQMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Cunninghamella echinulata	JEOL database	Messiano, G. B., et al, J. Nat. Prod. 73, 1933 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.41	ALOGPS
logP	4.13	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.84 m³·mol⁻¹	ChemAxon
Polarizability	41.44 Å³	ChemAxon
Number of Rings	3	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

50900772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Messiano, G. B., et al. (2010). Messiano, G. B., et al, J. Nat. Prod. 73, 1933 (2010). J. Nat. Prod..

Showing NP-Card for (-)-4'-O-demethyl-7-methoxyisogalbulin (NP0035686)

MOL for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

3D MOL for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

3D SDF for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

3D-SDF for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

PDB for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

3D PDB for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

SMILES for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

INCHI for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

Structure for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)

3D Structure for NP0035686 ((-)-4'-O-demethyl-7-methoxyisogalbulin)