NP-MRD: Showing NP-Card for (-)-4'-O-demethyl-8-hydroxyisogalbulin (NP0035685)

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Record Information

Version

2.0

Created at

2021-06-20 19:03:43 UTC

Updated at

2021-06-30 00:06:50 UTC

NP-MRD ID

NP0035685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-4'-O-demethyl-8-hydroxyisogalbulin

Provided By

JEOL Database JEOL Logo

Description

(2S)-2,3beta-Dimethyl-4alpha-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin-2alpha-ol 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-8-hydroxyisogalbulin is found in Cunninghamella echinulata. (-)-4'-O-demethyl-8-hydroxyisogalbulin was first documented in 2010 (Messiano, G. B., et al.). Based on a literature review very few articles have been published on (2S)-2,3beta-Dimethyl-4alpha-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin-2alpha-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121033D          

 52 54  0  0  0  0            999 V2000
    1.2091    2.1912   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307    1.8374    0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    1.0083    1.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    0.5427    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.3191    2.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -0.8483    2.1861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3450   -1.5889    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795   -2.5564    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417   -3.2564   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -4.1511   -1.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -4.1480   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302   -3.0266   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478   -3.6125   -2.7918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -5.0011   -2.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4951   -2.0749   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.3712   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5097   -0.3773    0.3093 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6438   -0.0747    1.8126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3259   -1.2351    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    1.0515    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.2995    2.3826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3278    0.7381    3.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -0.6987    3.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.2300    3.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.6141    2.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    1.0564    3.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    2.7784   -0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5653   -2.7433    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4027   -5.1464   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2903    0.5506   -0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2793    1.6301    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
  9 10  1  0  0  0  0
  8  7  1  0  0  0  0
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  4 30  1  0  0  0  0
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  1 27  1  0  0  0  0
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  1 29  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
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    1.8307    1.8374    0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3259   -1.2351    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    1.0515    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3278    0.7381    3.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -0.6987    3.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.2300    3.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.6141    2.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202121033D          

 52 54  0  0  0  0            999 V2000
    1.2091    2.1912   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307    1.8374    0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5300   -0.9757    3.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036   -1.4509    2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7373   -2.1564    2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1084    1.8232    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    1.1884    1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0981    1.5011    4.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    1.1768    4.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5499   -0.1055    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -1.3597    4.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -0.5191    4.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2793    1.6301    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
  9 10  1  0  0  0  0
  8  7  1  0  0  0  0
 10 11  1  0  0  0  0
 12  9  1  0  0  0  0
 18 20  1  6  0  0  0
 16 15  1  0  0  0  0
 18 19  1  0  0  0  0
 15 12  2  0  0  0  0
 21 22  1  0  0  0  0
 16 17  1  0  0  0  0
  5 23  1  0  0  0  0
  7  6  1  0  0  0  0
 23 24  2  0  0  0  0
  6 21  1  0  0  0  0
 24 25  1  0  0  0  0
 21 18  1  0  0  0  0
 25  3  2  0  0  0  0
 18 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 16  7  2  0  0  0  0
 25 26  1  0  0  0  0
  6  5  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 32  1  0  0  0  0
 15 39  1  0  0  0  0
  6 31  1  1  0  0  0
 21 46  1  6  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 20 45  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
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 24 51  1  0  0  0  0
  4 30  1  0  0  0  0
 26 52  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035685

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O5/c1-12-20(13-6-7-16(22)17(8-13)24-3)15-10-19(26-5)18(25-4)9-14(15)11-21(12,2)23/h6-10,12,20,22-23H,11H2,1-5H3/t12-,20+,21-/m0/s1

> <INCHI_KEY>
ILPKIWSJRANONE-QDEDPJFRSA-N

> <FORMULA>
C21H26O5

> <MOLECULAR_WEIGHT>
358.434

> <EXACT_MASS>
358.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.35158974624919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-2-ol

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.32857494

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.647582110161306

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.055417210221014

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9530022108834144

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
100.3336

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-1H-naphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    1.2091    2.1912   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307    1.8374    0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    1.0083    1.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    0.5427    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.3191    2.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -0.8483    2.1861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3450   -1.5889    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795   -2.5564    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417   -3.2564   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -4.1511   -1.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -4.1480   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302   -3.0266   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478   -3.6125   -2.7918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -5.0011   -2.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4951   -2.0749   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.3712   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5097   -0.3773    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6438   -0.0747    1.8126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3259   -1.2351    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    1.0515    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.2995    2.3826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3278    0.7381    3.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -0.6987    3.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.2300    3.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.6141    2.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    1.0564    3.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    2.7784   -0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    2.8186   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    1.3041   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7323    0.8238    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219   -1.6135    2.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.7433    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -4.5606    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -4.7989   -0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -3.1461   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -5.1464   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -5.4366   -3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6571   -5.5315   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216   -1.8972   -1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4762   -0.7278   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903    0.5506   -0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5300   -0.9757    3.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036   -1.4509    2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7373   -2.1564    2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1084    1.8232    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161    1.1884    1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0981    1.5011    4.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    1.1768    4.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5499   -0.1055    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -1.3597    4.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -0.5191    4.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2793    1.6301    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
  9 10  1  0
  8  7  1  0
 10 11  1  0
 12  9  1  0
 18 20  1  6
 16 15  1  0
 18 19  1  0
 15 12  2  0
 21 22  1  0
 16 17  1  0
  5 23  1  0
  7  6  1  0
 23 24  2  0
  6 21  1  0
 24 25  1  0
 21 18  1  0
 25  3  2  0
 18 17  1  0
  3  4  1  0
  4  5  2  0
 16  7  2  0
 25 26  1  0
  6  5  1  0
  3  2  1  0
  2  1  1  0
 12 13  1  0
 13 14  1  0
  8 32  1  0
 15 39  1  0
  6 31  1  1
 21 46  1  6
 17 40  1  0
 17 41  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 20 45  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
  4 30  1  0
 26 52  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 14 36  1  0
 14 37  1  0
 14 38  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       1.209   2.191  -0.357  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.831   1.837   0.874  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.120   1.008   1.703  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.178   0.543   1.488  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.795  -0.319   2.419  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.215  -0.848   2.186  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.345  -1.589   0.851  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.379  -2.556   0.493  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.442  -3.256  -0.720  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.488  -4.151  -1.127  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.755  -4.148  -0.435  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.530  -3.027  -1.571  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.748  -3.612  -2.792  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.442  -5.001  -2.868  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.495  -2.075  -1.223  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.428  -1.371  -0.011  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.510  -0.377   0.309  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.644  -0.075   1.813  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.326  -1.235   2.550  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.527   1.052   1.950  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.252   0.300   2.383  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.328   0.738   3.857  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.088  -0.699   3.573  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.205  -0.230   3.796  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.793   0.614   2.864  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.065   1.056   3.105  0.00  0.00           O+0
HETATM   27  H   UNK     0       0.301   2.778  -0.184  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.910   2.819  -0.916  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.999   1.304  -0.964  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.732   0.824   0.598  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.422  -1.613   2.949  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.565  -2.743   1.188  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.641  -4.561   0.573  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.442  -4.799  -0.983  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.196  -3.146  -0.407  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.403  -5.146  -3.177  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.077  -5.437  -3.645  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.657  -5.532  -1.933  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.322  -1.897  -1.909  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.476  -0.728  -0.077  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.290   0.551  -0.237  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.530  -0.976   3.595  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.304  -1.451   2.103  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.737  -2.156   2.532  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.108   1.823   1.532  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.916   1.188   1.828  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.098   1.501   4.007  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.380   1.177   4.185  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.550  -0.106   4.518  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.542  -1.360   4.309  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.752  -0.519   4.688  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.279   1.630   2.344  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3   25    4    2                                                  
CONECT    4    3    5   30                                                  
CONECT    5   23    4    6                                                  
CONECT    6    7   21    5   31                                             
CONECT    7    8    6   16                                                  
CONECT    8    9    7   32                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10   33   34   35                                             
CONECT   12    9   15   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   36   37   38                                             
CONECT   15   16   12   39                                                  
CONECT   16   15   17    7                                                  
CONECT   17   16   18   40   41                                             
CONECT   18   20   19   21   17                                             
CONECT   19   18   42   43   44                                             
CONECT   20   18   45                                                       
CONECT   21   22    6   18   46                                             
CONECT   22   21   47   48   49                                             
CONECT   23    5   24   50                                                  
CONECT   24   23   25   51                                                  
CONECT   25   24    3   26                                                  
CONECT   26   25   52                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   17                                                            
CONECT   41   17                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   26                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
    1.2091    2.1912   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307    1.8374    0.8736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    1.0083    1.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    0.5427    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.3191    2.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6438   -0.0747    1.8126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3259   -1.2351    2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    1.0515    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.2995    2.3826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3278    0.7381    3.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -0.6987    3.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.2300    3.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.6141    2.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    1.0564    3.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013    2.7784   -0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    2.8186   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    1.3041   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7323    0.8238    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219   -1.6135    2.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.7433    1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408   -4.5606    0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -4.7989   -0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -3.1461   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -5.1464   -3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -5.4366   -3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6571   -5.5315   -1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5300   -0.9757    3.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7373   -2.1564    2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0981    1.5011    4.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    1.1768    4.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5499   -0.1055    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -1.3597    4.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -0.5191    4.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2793    1.6301    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0
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  1 29  1  0
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 14 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-2,3b-Dimethyl-4a-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin-2a-ol	Generator
(2S)-2,3Β-dimethyl-4α-(3-methoxy-4-hydroxyphenyl)-6,7-dimethoxytetralin-2α-ol	Generator

Chemical Formula

C₂₁H₂₆O₅

Average Mass

358.4340 Da

Monoisotopic Mass

358.17802 Da

IUPAC Name

(2S,3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydronaphthalen-2-ol

Traditional Name

(2S,3S,4R)-4-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-1H-naphthalen-2-ol

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(C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2[H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H26O5/c1-12-20(13-6-7-16(22)17(8-13)24-3)15-10-19(26-5)18(25-4)9-14(15)11-21(12,2)23/h6-10,12,20,22-23H,11H2,1-5H3/t12-,20+,21-/m0/s1

InChI Key

ILPKIWSJRANONE-QDEDPJFRSA-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

Not Available

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
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	3.5	ALOGPS
logP	3.33	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.33 m³·mol⁻¹	ChemAxon
Polarizability	39.35 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

50900770

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-8-hydroxyisogalbulin (NP0035685)

MOL for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

3D MOL for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

3D SDF for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

3D-SDF for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

PDB for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

3D PDB for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

SMILES for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

INCHI for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

Structure for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)

3D Structure for NP0035685 ((-)-4'-O-demethyl-8-hydroxyisogalbulin)