NP-MRD: Showing NP-Card for (3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate (NP0265723)

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Record Information

Version

2.0

Created at

2022-09-08 09:48:37 UTC

Updated at

2022-09-08 09:48:37 UTC

NP-MRD ID

NP0265723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate

Description

(3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. (3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate is found in Conoideocrella tenuis. Based on a literature review very few articles have been published on (3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082211482D          

 47 52  0  0  1  0            999 V2000
   -4.9952    1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1747    0.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -1.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -1.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168   -1.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099    1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520    4.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    4.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139    3.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    4.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279    2.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349    2.6239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2898    1.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6488    2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5869    3.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3939    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3320    4.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250    4.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.9158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1121    1.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    2.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    1.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    0.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5410    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -0.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
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 17 18  1  0  0  0  0
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 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 14 27  2  0  0  0  0
 21 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 36  1  0  0  0  0
 13 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 11 47  1  0  0  0  0
M  END


  Mrv1652309082211482D          

 47 52  0  0  1  0            999 V2000
   -4.9952    1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1747    0.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -1.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -1.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168   -1.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099    1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    2.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070    3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520    4.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    4.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6139    3.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    4.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279    2.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349    2.6239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2898    1.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6488    2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5869    3.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3939    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3320    4.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250    4.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    0.9158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1121    1.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    2.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    1.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    0.5033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5410    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -0.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 14 27  2  0  0  0  0
 21 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 36  1  0  0  0  0
 13 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  6  0  0  0
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 46 47  1  0  0  0  0
 11 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(O)=C3CO[C@@H](C)[C@@H](OC(C)=O)C3=C(C2=C1)C1=C2C=C3[C@H](OC(C)=O)[C@H](C)OCC3=C(O)C2=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H36O12/c1-14-34(46-16(3)36)19-10-21-27(24(38)11-26(43-7)29(21)32(39)22(19)12-44-14)30-20-8-18(41-5)9-25(42-6)28(20)33(40)23-13-45-15(2)35(31(23)30)47-17(4)37/h8-11,14-15,34-35,38-40H,12-13H2,1-7H3/t14-,15-,34+,35+/m0/s1

> <INCHI_KEY>
IZLFEUFLSMAFJZ-GRHZFMAYSA-N

> <FORMULA>
C35H36O12

> <MOLECULAR_WEIGHT>
648.661

> <EXACT_MASS>
648.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
66.09501489672735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate

> <JCHEM_LOGP>
3.9244539906666676

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.38296808672258

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.824540490333303

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7726344239471072

> <JCHEM_POLAR_SURFACE_AREA>
159.44

> <JCHEM_REFRACTIVITY>
168.7359

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.324   1.870   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.793   1.709   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.459   0.939   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.459  -0.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.125  -1.371   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.125  -2.911   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.459  -3.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.792  -0.601   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.458  -1.371   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.458  -2.911   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.124  -0.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.124   0.939   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.458   1.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.952   3.570   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.455   4.196   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.476   5.034   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.506   6.179   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.030   7.643   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.476   7.964   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.013   5.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.043   7.003   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.567   8.468   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.550   6.683   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.025   5.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.995   4.074   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.489   4.394   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.532   4.898   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.008   3.433   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.514   3.113   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.544   4.258   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.990   1.649   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -8.562   6.042   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.069   5.722   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.086   7.507   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.580   7.827   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.792   0.939   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.125   1.709   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.209   1.709   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.209   3.249   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.543   4.019   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.543   5.559   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.877   3.249   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.543   0.939   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.877   1.709   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.543  -0.601   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       0.209  -1.371   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   37                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   47                                                  
CONECT   12   11   13   39                                                  
CONECT   13   12   14   37                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   36                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   14   21                                                  
CONECT   28   25   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   24                                                       
CONECT   37   13    8   38                                                  
CONECT   38   37    3                                                       
CONECT   39   12   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   39   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   11                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
(3S,4S)-5-[(3S,4S)-4-(Acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetic acid	Generator

Chemical Formula

C₃₅H₃₆O₁₂

Average Mass

648.6610 Da

Monoisotopic Mass

648.22068 Da

IUPAC Name

(3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate

Traditional Name

(3S,4S)-5-[(3S,4S)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-4-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(O)=C3CO[C@@H](C)[C@@H](OC(C)=O)C3=C(C2=C1)C1=C2C=C3[C@H](OC(C)=O)[C@H](C)OCC3=C(O)C2=C(OC)C=C1O

InChI Identifier

InChI=1S/C35H36O12/c1-14-34(46-16(3)36)19-10-21-27(24(38)11-26(43-7)29(21)32(39)22(19)12-44-14)30-20-8-18(41-5)9-25(42-6)28(20)33(40)23-13-45-15(2)35(31(23)30)47-17(4)37/h8-11,14-15,34-35,38-40H,12-13H2,1-7H3/t14-,15-,34+,35+/m0/s1

InChI Key

IZLFEUFLSMAFJZ-GRHZFMAYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Conoideocrella tenuis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
Naphthopyran
1-naphthol
2-naphthol
2-benzopyran
Naphthalene
Isochromane
Benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.92	ChemAxon
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	159.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	168.74 m³·mol⁻¹	ChemAxon
Polarizability	66.1 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

78442417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate (NP0265723)

MOL for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

3D MOL for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

3D SDF for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

3D-SDF for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

PDB for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

3D PDB for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

SMILES for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

INCHI for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

Structure for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)

3D Structure for NP0265723 ((3s,4s)-5-[(3s,4s)-4-(acetyloxy)-7,10-dihydroxy-9-methoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-6-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-1h,3h,4h-naphtho[2,3-c]pyran-4-yl acetate)