NP-MRD: Showing NP-Card for podophyllum resin (NP0315331)

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Record Information

Version

2.0

Created at

2022-09-11 13:54:59 UTC

Updated at

2022-09-11 13:54:59 UTC

NP-MRD ID

NP0315331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

podophyllum resin

Description

16-Hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-12-one belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). podophyllum resin is found in Anthriscus sylvestris, Condea verticillata, Diphylleia grayi, Dysosma versipellis, Eriope blanchetii, Hernandia sonora, Juniperus chinensis, Juniperus thurifera, Linum album, Linum cariense, Linum flavum, Podophyllum peltatum and Sinopodophyllum hexandrum. 16-Hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-12-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121513282D          

 30 34  0  0  0  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    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
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   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
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -0.7149    1.7890    3.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890    1.5860    2.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9415    0.8074    1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8054    0.1604    1.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -0.6404    0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3503   -1.3543   -0.3667 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2322   -0.5407   -1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238   -0.2319   -2.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    0.5391   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9265    1.0366   -2.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2456    0.7342   -1.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034   -0.0486   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8293   -0.3090    0.6831 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7762    0.8565    1.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2084   -1.4655    1.3600 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1872   -2.6016    1.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -3.5296    0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5551   -3.3760    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020   -4.1842   -0.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -2.1007    0.7367 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5160    1.7557   -3.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5633    2.0493   -4.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.9741   -4.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -0.7682   -0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -0.1204   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3835   -0.2357   -0.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974   -1.0309   -1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466    0.6742    1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476    1.3425    1.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    2.6385    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879    1.9450    3.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7869    2.6983    4.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    0.9486    4.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.2813    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -2.1522   -1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095   -0.5859   -2.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1744    1.1275   -1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411   -0.5253    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6947    1.6115    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169   -1.1315    2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -2.2507    1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055   -3.0872    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -2.3588    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    2.0507   -5.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1192    3.0272   -4.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -1.3815   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872   -2.0438   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8952   -0.5774   -2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5595   -1.0034   -2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    3.1922    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5913    2.5863    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8647    3.2233    2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
  5  6  1  0
  6 20  1  0
 20 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 23  1  0
 23 22  1  0
 22 21  1  0
  9  8  1  0
  8  7  2  0
 28  3  1  0
  7  6  1  0
 18 20  1  0
  7 12  1  0
 21 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
  6 35  1  6
 20 43  1  1
 15 40  1  1
 16 41  1  0
 16 42  1  0
 13 38  1  6
 14 39  1  0
 11 37  1  0
 22 44  1  0
 22 45  1  0
  8 36  1  0
M  END


  Mrv0541 04121513282D          

 30 34  0  0  0  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    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
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   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
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3

> <INCHI_KEY>
YJGVMLPVUAXIQN-UHFFFAOYSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.6697944198208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.6227982693333332

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.015751296514601

> <JCHEM_PKA_STRONGEST_BASIC>
-3.229310382904514

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
103.90499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
picropodophyllin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       3.590 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   30                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   13   22                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Ardern brand OF podophyllotoxin	MeSH
CPH86	MeSH
Canderm brand OF podophyllotoxin	MeSH
Condyline	MeSH
Condylox	MeSH
Epipodophyllotoxin	MeSH
Fides ecopharma brand OF podophyllotoxin	MeSH
Hamilton brand OF podophyllotoxin	MeSH
Newport brand OF podophyllotoxin	MeSH
Oclassen brand OF podophyllotoxin	MeSH
Paddock brand OF podophyllotoxin	MeSH
Paladin brand OF podophyllotoxin	MeSH
PODOCON-25	MeSH
Podofilm	MeSH
Podofilox	MeSH
Podophyllotoxin	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	MeSH
Stiefel brand OF podophyllotoxin	MeSH
Wartec	MeSH
Warticon	MeSH
Wolff brand OF podophyllotoxin	MeSH
Yamanouchi brand OF podophyllotoxin	MeSH

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Traditional Name

picropodophyllin

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3

InChI Key

YJGVMLPVUAXIQN-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Anthriscus sylvestris	LOTUS Database	35616633
Condea verticillata	LOTUS Database	35616633
Diphylleia grayi	LOTUS Database	35616633
Dysosma versipellis	LOTUS Database	35616633
Eriope blanchetii	LOTUS Database	35616633
Hernandia sonora	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Linum album	LOTUS Database	35616633
Linum cariense	LOTUS Database	35616633
Linum flavum	LOTUS Database	35616633
Podophyllum peltatum	LOTUS Database	35616633
Sinopodophyllum hexandrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Tetralin
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a lignan (CPD-8959 )

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	2.37	ALOGPS
logP	1.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	41.67 Å³	ChemAxon
Number of Rings	5	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

4865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for podophyllum resin (NP0315331)

MOL for NP0315331 (podophyllum resin)

3D MOL for NP0315331 (podophyllum resin)

3D SDF for NP0315331 (podophyllum resin)

3D-SDF for NP0315331 (podophyllum resin)

PDB for NP0315331 (podophyllum resin)

3D PDB for NP0315331 (podophyllum resin)

SMILES for NP0315331 (podophyllum resin)

INCHI for NP0315331 (podophyllum resin)

Structure for NP0315331 (podophyllum resin)

3D Structure for NP0315331 (podophyllum resin)