NP-MRD: Showing NP-Card for (-)-Pluviatolide (NP0054881)

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Record Information

Version

2.0

Created at

2022-04-28 01:05:32 UTC

Updated at

2022-04-28 01:05:32 UTC

NP-MRD ID

NP0054881

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Pluviatolide

Description

(-)-Pluviatolide belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-pluviatolide 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. (-)-Pluviatolide is found in Bupleurum salicifolium, Chamaecyparis formosensis, Chamaecyparis obtusa, Juniperus chinensis, Syringa pinnatifolia, Taiwania cryptomerioides, Torreya jackii and Zanthoxylum pluviatile. (-)-Pluviatolide was first documented in 2003 (PMID: 12956064). Based on a literature review a small amount of articles have been published on (-)-pluviatolide (PMID: 23161544) (PMID: 33095000) (PMID: 25769897) (PMID: 18570470).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203052D          

 26 29  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    3.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    5.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    5.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    4.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    5.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    3.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    4.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.2901   -0.5715   -2.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9212    0.0934   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951    0.1973   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0459   -0.3276    0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -0.2247    1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -0.8174    1.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.0717    1.2317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1281    1.2825    2.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060    1.2902    3.3154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.4119    1.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241    2.0234   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415    0.6371   -0.1752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8024   -0.2241   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945   -0.5874   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928   -1.7109   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201   -2.0407   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.1960   -0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353   -0.0649   -1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801    0.2341   -1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7137    0.5669   -1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8132   -0.2678   -1.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3032   -1.2743   -0.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501    0.4272    2.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3005    0.9506    2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282    0.8486    0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2007    1.4024    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146   -0.2500   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -1.6652   -2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570   -0.3558   -3.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690   -0.8439   -0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946   -1.1644    2.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466   -1.7428    0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -0.5763    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    2.7623   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8095    2.0814   -0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    0.7968   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    0.2789   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1768   -1.1516   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697   -2.3994    0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1931   -2.9346    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9994    1.1433   -1.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5765    0.2835   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2298   -0.7171   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    0.5414    3.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8034    1.4673    2.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6372    1.3162   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 23  5  1  0
  5  6  1  0
  6  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  5  4  2  0
  4  3  1  0
  8  7  1  0
 19 14  1  0
 18 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 46  1  0
 24 45  1  0
 23 44  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
 12 36  1  6
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 21 42  1  0
 21 43  1  0
 19 41  1  0
 11 34  1  0
 11 35  1  0
  4 30  1  0
M  END


  Mrv1652304282203052D          

 26 29  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    3.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016    3.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754    5.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    5.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    4.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    5.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    3.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    4.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(C[C@@H]2[C@@H](CC3=CC=C4OCOC4=C3)COC2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-23-18-8-13(2-4-16(18)21)7-15-14(10-24-20(15)22)6-12-3-5-17-19(9-12)26-11-25-17/h2-5,8-9,14-15,21H,6-7,10-11H2,1H3/t14-,15+/m0/s1

> <INCHI_KEY>
OCTZTNYFALPGHW-LSDHHAIUSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.374

> <EXACT_MASS>
356.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.21327967937842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.376252566

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945546155194782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.508065617964526

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
92.95720000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.345   6.828   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.821   8.293   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.916   9.539   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.361   8.293   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.837   6.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.881   6.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.736   7.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.272   6.907   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.127   7.937   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.447   9.444   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.912   9.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.057   8.889   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.303  10.474   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.337   7.461   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.482   8.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2   18                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    2                                                       
CONECT    8    3    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
CONECT   16   11   17                                                       
CONECT   17   16                                                            
CONECT   18    1   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Pluviatolide	ChEBI

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3740 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

(3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

(3R,4R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(C[C@@H]2[C@@H](CC3=CC=C4OCOC4=C3)COC2=O)=C1

InChI Identifier

InChI=1S/C20H20O6/c1-23-18-8-13(2-4-16(18)21)7-15-14(10-24-20(15)22)6-12-3-5-17-19(9-12)26-11-25-17/h2-5,8-9,14-15,21H,6-7,10-11H2,1H3/t14-,15+/m0/s1

InChI Key

OCTZTNYFALPGHW-LSDHHAIUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Bupleurum salicifolium	Plant	KNApSAcK
Chamaecyparis formosensis	Plant	KNApSAcK
Chamaecyparis obtusa	Plant	KNApSAcK
Juniperus chinensis	Plant	KNApSAcK
Syringa pinnatifolia	LOTUS Database	35616633
Taiwania cryptomerioides	Plant	KNApSAcK
Torreya jackii	Plant	KNApSAcK
Zanthoxylum pluviatile	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.86	ALOGPS
logP	3.38	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.96 m³·mol⁻¹	ChemAxon
Polarizability	37.21 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

C00007201

Chemspider ID

147623

KEGG Compound ID

Not Available

BioCyc ID

CPD-17597

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168759

PDB ID

Not Available

ChEBI ID

90896

Good Scents ID

rw1486871

References

General References

Marques JV, Kim KW, Lee C, Costa MA, May GD, Crow JA, Davin LB, Lewis NG: Next generation sequencing in predicting gene function in podophyllotoxin biosynthesis. J Biol Chem. 2013 Jan 4;288(1):466-79. doi: 10.1074/jbc.M112.400689. Epub 2012 Nov 16. [PubMed:23161544 ]
Decembrino D, Ricklefs E, Wohlgemuth S, Girhard M, Schullehner K, Jach G, Urlacher VB: Assembly of Plant Enzymes in E. coli for the Production of the Valuable (-)-Podophyllotoxin Precursor (-)-Pluviatolide. ACS Synth Biol. 2020 Nov 20;9(11):3091-3103. doi: 10.1021/acssynbio.0c00354. Epub 2020 Oct 23. [PubMed:33095000 ]
Lu P, Wang NN, Wu JM, Xue PF: Chemical constituents from Mongolian herb Syringa pinnatifolia var. alashanensis. Chin J Nat Med. 2015 Feb;13(2):142-4. doi: 10.1016/S1875-5364(15)60018-8. [PubMed:25769897 ]
Zhang G, Shimokawa S, Mochizuki M, Kumamoto T, Nakanishi W, Watanabe T, Ishikawa T, Matsumoto K, Tashima K, Horie S, Higuchi Y, Dominguez OP: Chemical constituents of Aristolochia constricta: antispasmodic effects of its constituents in guinea-pig ileum and isolation of a diterpeno-lignan hybrid. J Nat Prod. 2008 Jul;71(7):1167-72. doi: 10.1021/np800041t. Epub 2008 Jun 21. [PubMed:18570470 ]
Sakakibara N, Suzuki S, Umezawa T, Shimada M: Biosynthesis of yatein in Anthriscus sylvestris. Org Biomol Chem. 2003 Jul 21;1(14):2474-85. doi: 10.1039/b304411d. [PubMed:12956064 ]

Showing NP-Card for (-)-Pluviatolide (NP0054881)

MOL for NP0054881 ((-)-Pluviatolide)

3D MOL for NP0054881 ((-)-Pluviatolide)

3D SDF for NP0054881 ((-)-Pluviatolide)

3D-SDF for NP0054881 ((-)-Pluviatolide)

PDB for NP0054881 ((-)-Pluviatolide)

3D PDB for NP0054881 ((-)-Pluviatolide)

SMILES for NP0054881 ((-)-Pluviatolide)

INCHI for NP0054881 ((-)-Pluviatolide)

Structure for NP0054881 ((-)-Pluviatolide)

3D Structure for NP0054881 ((-)-Pluviatolide)