NP-MRD: Showing NP-Card for (+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+ (NP0035964)

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Record Information

Version

1.0

Created at

2021-06-20 19:15:51 UTC

Updated at

2021-06-30 00:07:21 UTC

NP-MRD ID

NP0035964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+

Provided By

JEOL Database JEOL Logo

Description

(+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cyclolignan-9'-ol belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton (+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cyclolignan-9'-ol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+ is found in Bambusa emeiensis, Lyonia ovalifolia and Sinocalamus affinis. It was first documented in 2011 (PMID: 21469695). Based on a literature review very few articles have been published on (+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cyclolignan-9'-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121153D          

 56 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121153D          

 56 59  0  0  0  0            999 V2000
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   -3.0326   -3.1340    2.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    2.5155    3.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.8893    4.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    4.1864    3.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    0.7675    3.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    1.8082   -2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    1.6125   -3.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963    3.0975   -2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    4.1838    0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299   -0.8061   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573   -2.8565   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -4.1454   -3.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -2.4110   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -3.4841   -5.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -2.5694   -5.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838   -0.2064   -4.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5098   -1.5608   -4.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -0.0931   -4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -3.6149    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -4.1164    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -3.5140    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -1.4050    3.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144   -1.6732    2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -3.2572   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994   -1.9152    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -1.1412    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -2.9279    2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
 17 18  1  0  0  0  0
 28 12  1  0  0  0  0
 26 27  1  0  0  0  0
 13 21  1  0  0  0  0
 12  6  1  0  0  0  0
 21 19  2  0  0  0  0
  3 10  2  0  0  0  0
 25 24  1  0  0  0  0
 10  7  1  0  0  0  0
  7  6  2  0  0  0  0
 19 16  1  0  0  0  0
  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
 16 15  2  0  0  0  0
  7  8  1  0  0  0  0
 15 14  1  0  0  0  0
 10 11  1  0  0  0  0
 24 14  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
 26 25  1  0  0  0  0
  8  9  1  0  0  0  0
  5 27  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  1  0  0  0  0
 28 26  1  0  0  0  0
 28 29  1  0  0  0  0
 21 22  1  0  0  0  0
 29 30  1  0  0  0  0
 28 53  1  6  0  0  0
 26 50  1  1  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 12 39  1  6  0  0  0
 15 40  1  0  0  0  0
 20 44  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
  4 34  1  0  0  0  0
 11 38  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 23 45  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
 30 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C2=C(OC([H])([H])[C@@]3([H])C([H])([H])C4=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C4[C@]2([H])[C@]3([H])C([H])([H])O[H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O8/c1-26-14-6-10-5-11-9-30-13-7-15(27-2)20(25)22(29-4)18(13)17(12(11)8-23)16(10)21(28-3)19(14)24/h6-7,11-12,17,23-25H,5,8-9H2,1-4H3/t11-,12-,17+/m1/s1

> <INCHI_KEY>
VCZWWJGHKZTTAS-QFSBIZTOSA-N

> <FORMULA>
C22H26O8

> <MOLECULAR_WEIGHT>
418.442

> <EXACT_MASS>
418.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.408331981317964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S,18S)-18-(hydroxymethyl)-3,5,14,16-tetramethoxy-8-oxatetracyclo[8.7.1.0^{2,7}.0^{12,17}]octadeca-2(7),3,5,12,14,16-hexaene-4,15-diol

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.8260016073333332

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.046880978285927

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.435460097695007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.612203319782531

> <JCHEM_POLAR_SURFACE_AREA>
106.84000000000002

> <JCHEM_REFRACTIVITY>
109.00090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S,18S)-18-(hydroxymethyl)-3,5,14,16-tetramethoxy-8-oxatetracyclo[8.7.1.0^{2,7}.0^{12,17}]octadeca-2(7),3,5,12,14,16-hexaene-4,15-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    1.8853    3.2021    3.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918    3.3342    2.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    2.1903    1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510    0.9305    2.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -0.1684    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -0.0019    0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    1.2724   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815    1.4063   -1.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149    2.0197   -2.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.3534    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448    3.6142   -0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.1858   -0.3764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1110   -1.7033   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -2.1673   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -2.5435   -2.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -2.5366   -3.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -2.9095   -4.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838   -3.2519   -4.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2707   -2.1482   -3.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -2.2292   -5.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5855   -1.7210   -2.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -1.3727   -3.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705   -0.7857   -4.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7018   -2.2536   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129   -3.2458    0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.7021    1.5172 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1471   -1.4944    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.3591    0.5556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6860   -2.0478    1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -3.1340    2.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    2.5155    3.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.8893    4.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    4.1864    3.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    0.7675    3.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    1.8082   -2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    1.6125   -3.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963    3.0975   -2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    4.1838    0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299   -0.8061   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573   -2.8565   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -4.1454   -3.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -2.4110   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -3.4841   -5.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -2.5694   -5.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838   -0.2064   -4.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5098   -1.5608   -4.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -0.0931   -4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -3.6149    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -4.1164    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -3.5140    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -1.4050    3.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144   -1.6732    2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -3.2572   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994   -1.9152    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -1.1412    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -2.9279    2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
 17 18  1  0
 28 12  1  0
 26 27  1  0
 13 21  1  0
 12  6  1  0
 21 19  2  0
  3 10  2  0
 25 24  1  0
 10  7  1  0
  7  6  2  0
 19 16  1  0
  6  5  1  0
 12 13  1  0
  5  4  2  0
  4  3  1  0
 16 15  2  0
  7  8  1  0
 15 14  1  0
 10 11  1  0
 24 14  1  0
  3  2  1  0
 16 17  1  0
  2  1  1  0
 26 25  1  0
  8  9  1  0
  5 27  1  0
 19 20  1  0
 22 23  1  0
 28 26  1  0
 28 29  1  0
 21 22  1  0
 29 30  1  0
 28 53  1  6
 26 50  1  1
 25 48  1  0
 25 49  1  0
 12 39  1  6
 15 40  1  0
 20 44  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 27 51  1  0
 27 52  1  0
  4 34  1  0
 11 38  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 29 54  1  0
 29 55  1  0
 30 56  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       1.885   3.202   3.601  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.292   3.334   2.314  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.782   2.190   1.751  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.751   0.931   2.341  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.185  -0.168   1.666  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.365  -0.002   0.374  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.310   1.272  -0.229  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.882   1.406  -1.470  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.015   2.020  -2.422  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.242   2.353   0.470  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.245   3.614  -0.077  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.987  -1.186  -0.376  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.111  -1.703  -1.521  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.192  -2.167  -1.272  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.053  -2.543  -2.305  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.595  -2.537  -3.616  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.319  -2.910  -4.723  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.684  -3.252  -4.504  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.271  -2.148  -3.879  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.159  -2.229  -5.182  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.586  -1.721  -2.852  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.903  -1.373  -3.016  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.271  -0.786  -4.257  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.702  -2.254  -0.003  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.013  -3.246   0.765  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.214  -2.702   1.517  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.147  -1.494   2.391  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.371  -2.359   0.556  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.686  -2.048   1.293  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.033  -3.134   2.145  0.00  0.00           O+0
HETATM   31  H   UNK     0       2.738   2.515   3.575  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.146   2.889   4.346  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.260   4.186   3.898  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.153   0.768   3.337  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.044   1.808  -2.233  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.261   1.613  -3.407  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.196   3.098  -2.462  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.645   4.184   0.608  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.930  -0.806  -0.790  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.057  -2.857  -2.043  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.769  -4.145  -3.877  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.239  -2.411  -4.076  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.129  -3.484  -5.477  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.609  -2.569  -5.682  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.184  -0.206  -4.088  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.510  -1.561  -4.991  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.512  -0.093  -4.636  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.738  -3.615   1.500  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.746  -4.116   0.149  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.535  -3.514   2.183  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.595  -1.405   3.195  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.114  -1.673   2.878  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.573  -3.257  -0.047  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.499  -1.915   0.571  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.622  -1.141   1.901  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.906  -2.928   2.520  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3   10    4    2                                                  
CONECT    4    5    3   34                                                  
CONECT    5    6    4   27                                                  
CONECT    6   12    7    5                                                  
CONECT    7   10    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   35   36   37                                             
CONECT   10    3    7   11                                                  
CONECT   11   10   38                                                       
CONECT   12   28    6   13   39                                             
CONECT   13   14   21   12                                                  
CONECT   14   13   15   24                                                  
CONECT   15   16   14   40                                                  
CONECT   16   19   15   17                                                  
CONECT   17   18   16                                                       
CONECT   18   17   41   42   43                                             
CONECT   19   21   16   20                                                  
CONECT   20   19   44                                                       
CONECT   21   13   19   22                                                  
CONECT   22   23   21                                                       
CONECT   23   22   45   46   47                                             
CONECT   24   25   14                                                       
CONECT   25   24   26   48   49                                             
CONECT   26   27   25   28   50                                             
CONECT   27   26    5   51   52                                             
CONECT   28   12   26   29   53                                             
CONECT   29   28   30   54   55                                             
CONECT   30   29   56                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   15                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   20                                                            
CONECT   45   23                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
    1.8853    3.2021    3.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918    3.3342    2.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824    2.1903    1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510    0.9305    2.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -0.1684    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -0.0019    0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    1.2724   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815    1.4063   -1.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149    2.0197   -2.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.3534    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448    3.6142   -0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.1858   -0.3764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1110   -1.7033   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -2.1673   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -2.5435   -2.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -2.5366   -3.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192   -2.9095   -4.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838   -3.2519   -4.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2707   -2.1482   -3.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -2.2292   -5.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5855   -1.7210   -2.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9025   -1.3727   -3.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705   -0.7857   -4.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7018   -2.2536   -0.0026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129   -3.2458    0.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.7021    1.5172 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1471   -1.4944    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.3591    0.5556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6860   -2.0478    1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -3.1340    2.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7379    2.5155    3.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.8893    4.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599    4.1864    3.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    0.7675    3.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    1.8082   -2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    1.6125   -3.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963    3.0975   -2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    4.1838    0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299   -0.8061   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573   -2.8565   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693   -4.1454   -3.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -2.4110   -4.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -3.4841   -5.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6088   -2.5694   -5.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1838   -0.2064   -4.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5098   -1.5608   -4.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118   -0.0931   -4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -3.6149    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461   -4.1164    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -3.5140    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -1.4050    3.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144   -1.6732    2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -3.2572   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994   -1.9152    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -1.1412    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -2.9279    2.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
 17 18  1  0
 28 12  1  0
 26 27  1  0
 13 21  1  0
 12  6  1  0
 21 19  2  0
  3 10  2  0
 25 24  1  0
 10  7  1  0
  7  6  2  0
 19 16  1  0
  6  5  1  0
 12 13  1  0
  5  4  2  0
  4  3  1  0
 16 15  2  0
  7  8  1  0
 15 14  1  0
 10 11  1  0
 24 14  1  0
  3  2  1  0
 16 17  1  0
  2  1  1  0
 26 25  1  0
  8  9  1  0
  5 27  1  0
 19 20  1  0
 22 23  1  0
 28 26  1  0
 28 29  1  0
 21 22  1  0
 29 30  1  0
 28 53  1  6
 26 50  1  1
 25 48  1  0
 25 49  1  0
 12 39  1  6
 15 40  1  0
 20 44  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 27 51  1  0
 27 52  1  0
  4 34  1  0
 11 38  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₈

Average Mass

418.4420 Da

Monoisotopic Mass

418.16277 Da

IUPAC Name

(1S,10S,18S)-18-(hydroxymethyl)-3,5,14,16-tetramethoxy-8-oxatetracyclo[8.7.1.0^{2,7}.0^{12,17}]octadeca-2(7),3,5,12,14,16-hexaene-4,15-diol

Traditional Name

(1S,10S,18S)-18-(hydroxymethyl)-3,5,14,16-tetramethoxy-8-oxatetracyclo[8.7.1.0^{2,7}.0^{12,17}]octadeca-2(7),3,5,12,14,16-hexaene-4,15-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C2=C(OC([H])([H])[C@@]3([H])C([H])([H])C4=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C4[C@]2([H])[C@]3([H])C([H])([H])O[H])C([H])=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C22H26O8/c1-26-14-6-10-5-11-9-30-13-7-15(27-2)20(25)22(29-4)18(13)17(12(11)8-23)16(10)21(28-3)19(14)24/h6-7,11-12,17,23-25H,5,8-9H2,1-4H3/t11-,12-,17+/m1/s1

InChI Key

VCZWWJGHKZTTAS-QFSBIZTOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Bambusa emeiensis	LOTUS Database	35616633
Lyonia ovalifolia	LOTUS Database	35616633
Sinocalamus affinis	JEOL database	Xiong, L., et al, J. Nat. Prod. 74, 1188 (2011)

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
Benzoxepine
Tetralin
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:67622 )
polyphenol (CHEBI:67622 )
primary alcohol (CHEBI:67622 )
lignan (CHEBI:67622 )

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	1.88	ALOGPS
logP	1.83	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109 m³·mol⁻¹	ChemAxon
Polarizability	43.41 Å³	ChemAxon
Number of Rings	4	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

26647870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

67622

Good Scents ID

Not Available

References

General References

Xiong L, Zhu C, Li Y, Tian Y, Lin S, Yuan S, Hu J, Hou Q, Chen N, Yang Y, Shi J: Lignans and neolignans from Sinocalamus affinis and their absolute configurations. J Nat Prod. 2011 May 27;74(5):1188-200. doi: 10.1021/np200117y. Epub 2011 Apr 6. [PubMed:21469695 ]
Xiong, L., et al. (2011). Xiong, L., et al, J. Nat. Prod. 74, 1188 (2011). J. Nat. Prod..

Showing NP-Card for (+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+ (NP0035964)

MOL for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

3D MOL for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

3D SDF for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

3D-SDF for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

PDB for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

3D PDB for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

SMILES for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

INCHI for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

Structure for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)

3D Structure for NP0035964 ((+)-(7'S,8S,8'S)-3',4-dihydroxy-2',3,4',5-tetramethoxy-6',9-epoxy-2,7'-cy+)