NP-MRD: Showing NP-Card for Podophyllotoxin (NP0006533)

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Record Information

Version

1.0

Created at

2020-12-09 03:31:23 UTC

Updated at

2021-08-19 23:59:40 UTC

NP-MRD ID

NP0006533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Podophyllotoxin

Provided By

NPAtlas

Description

Podofilox, also known as condylox or podophyllotoxin 7, 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). Podofilox is a drug which is used for treatment of external genital warts (condyloma acuminatum). Podofilox is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Podophyllotoxin is found in Condea verticillata, Dysosma pleiantha, Dysosma versipellis, Eriope blanchetii, Hernandia ovigera, Hernandia sonora, Juniperus thurifera var.africana, Linum flavum, Linum mucronatum, Linum nodiflorum, Linum tauricum, Phialocephala fortinii and Sinopodophyllum emodi WALL.. It was first documented in 2005 (PMID: 15803102). Based on a literature review a significant number of articles have been published on Podofilox (PMID: 16933860) (PMID: 22621772) (PMID: 23161544) (PMID: 23798883).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118283D          

 52 56  0  0  0  0            999 V2000
   -2.7302    1.0183    3.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531    1.1779    2.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    0.7234    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4513    0.1269    1.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -0.3455    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.9642    0.6209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6818    0.0179    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.2939    1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    2.2268    1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697    1.9142    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0931   -1.5887   -0.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1558   -1.6083   -1.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7742   -1.9260   -1.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7152   -3.2537   -1.9842 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  6 35  1  1  0  0  0
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 11 37  1  0  0  0  0
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 30 50  1  0  0  0  0
 30 51  1  0  0  0  0
 30 52  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118283D          

 52 56  0  0  0  0            999 V2000
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    1.4624   -1.1047   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444   -3.2044   -3.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -3.9871   -1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -2.9746    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245    4.7099    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    4.5828    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -0.5435   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    0.2418   -4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.0415   -3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.5484   -3.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4676   -0.4175   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2842    0.8726    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2797    0.9762   -0.8665 H   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
  7  8  2  0  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  1  0  0  0  0
 13 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
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 24  2  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
 25 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28  3  1  0  0  0  0
 20  6  1  0  0  0  0
 12  7  1  0  0  0  0
 20 15  1  0  0  0  0
 23  9  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
  4 34  1  0  0  0  0
  6 35  1  1  0  0  0
  8 36  1  0  0  0  0
 11 37  1  0  0  0  0
 13 38  1  1  0  0  0
 14 39  1  0  0  0  0
 15 40  1  6  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 20 43  1  1  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 24 46  1  0  0  0  0
 27 47  1  0  0  0  0
 27 48  1  0  0  0  0
 27 49  1  0  0  0  0
 30 50  1  0  0  0  0
 30 51  1  0  0  0  0
 30 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C([H])C3=C(OC([H])([H])O3)C([H])=C2[C@@]([H])(C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2[H])[C@@]2([H])C(=O)OC([H])([H])[C@]12[H]

> <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/t13-,18+,19-,20-/m0/s1

> <INCHI_KEY>
YJGVMLPVUAXIQN-XVVDYKMHSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.4053

> <EXACT_MASS>
414.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.77514470614504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]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>
92.68000000000002

> <JCHEM_REFRACTIVITY>
103.905

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -2.7302    1.0183    3.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531    1.1779    2.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    0.7234    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4513    0.1269    1.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -0.3455    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.9642    0.6209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6818    0.0179    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.2939    1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    2.2268    1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697    1.9142    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936    0.6611   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656   -0.2682   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931   -1.5887   -0.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1558   -1.6083   -1.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7742   -1.9260   -1.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7152   -3.2537   -1.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3054   -3.5246   -1.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384   -2.8691   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -2.9356   -0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -2.1984   -0.1270 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6737    2.9602    0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    4.0845    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    3.5344    1.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -0.1918   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5941    0.4020   -0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    0.5460   -2.2383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    0.0614   -3.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    0.8540    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4996    1.4449   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    0.6612    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8399    1.6898    3.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -0.0479    3.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4156    1.2715    4.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    0.0197    2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -1.2778    1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    1.5809    1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    0.3895   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574   -2.3137    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9803   -2.0053   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -1.1047   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444   -3.2044   -3.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -3.9871   -1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -2.9746    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245    4.7099    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    4.5828    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -0.5435   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    0.2418   -4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.0415   -3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.5484   -3.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4676   -0.4175   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2842    0.8726    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2797    0.9762   -0.8665 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  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  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
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  1
  8 36  1  0
 11 37  1  0
 13 38  1  1
 14 39  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
 20 43  1  1
 22 44  1  0
 22 45  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
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.730   1.018   3.801  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.353   1.178   2.540  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.692   0.723   1.404  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.451   0.127   1.493  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.745  -0.346   0.392  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.580  -0.964   0.621  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.682   0.018   0.556  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.558   1.294   1.114  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.581   2.227   1.066  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.770   1.914   0.454  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.894   0.661  -0.095  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.866  -0.268  -0.043  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.093  -1.589  -0.667  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.156  -1.608  -1.543  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.774  -1.926  -1.306  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.715  -3.254  -1.984  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.305  -3.525  -1.897  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.238  -2.869  -0.799  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.484  -2.936  -0.553  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.857  -2.198  -0.127  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.674   2.960   0.500  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.948   4.085   0.983  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.740   3.534   1.520  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.344  -0.192  -0.821  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.594   0.402  -0.975  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.186   0.546  -2.238  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.456   0.061  -3.348  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.253   0.854   0.152  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.500   1.445  -0.011  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.670   0.661   0.030  0.00  0.00           C+0
HETATM   31  H   UNK     0      -1.840   1.690   3.824  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.442  -0.048   3.950  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.416   1.272   4.625  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.996   0.020   2.492  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.585  -1.278   1.719  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.636   1.581   1.606  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.818   0.390  -0.581  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.257  -2.314   0.168  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.980  -2.005  -1.169  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.462  -1.105  -1.946  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.044  -3.204  -3.037  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.303  -3.987  -1.410  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.394  -2.975   0.482  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.724   4.710   0.091  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.558   4.583   1.740  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.828  -0.544  -1.703  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.975   0.242  -4.305  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.269  -1.042  -3.268  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.462   0.548  -3.419  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.468  -0.418  -0.119  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.284   0.873   0.910  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.280   0.976  -0.867  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   34                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   20   35                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9   36                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12   14   15   38                                             
CONECT   14   13   39                                                       
CONECT   15   13   16   20   40                                             
CONECT   16   15   17   41   42                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   15   43                                             
CONECT   21   10   22                                                       
CONECT   22   21   23   44   45                                             
CONECT   23   22    9                                                       
CONECT   24    5   25   46                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   47   48   49                                             
CONECT   28   25   29    3                                                  
CONECT   29   28   30                                                       
CONECT   30   29   50   51   52                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   20                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   27                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
CONECT   50   30                                                            
CONECT   51   30                                                            
CONECT   52   30                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
   -2.7302    1.0183    3.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531    1.1779    2.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    0.7234    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4513    0.1269    1.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -0.3455    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -0.9642    0.6209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6818    0.0179    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.2939    1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    2.2268    1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697    1.9142    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8936    0.6611   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656   -0.2682   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931   -1.5887   -0.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1558   -1.6083   -1.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7742   -1.9260   -1.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7152   -3.2537   -1.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3054   -3.5246   -1.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384   -2.8691   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -2.9356   -0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -2.1984   -0.1270 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6737    2.9602    0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    4.0845    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    3.5344    1.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441   -0.1918   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5941    0.4020   -0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    0.5460   -2.2383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    0.0614   -3.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    0.8540    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4996    1.4449   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    0.6612    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8399    1.6898    3.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -0.0479    3.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4156    1.2715    4.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957    0.0197    2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -1.2778    1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    1.5809    1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8176    0.3895   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574   -2.3137    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9803   -2.0053   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -1.1047   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444   -3.2044   -3.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -3.9871   -1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -2.9746    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245    4.7099    0.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    4.5828    1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -0.5435   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    0.2418   -4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.0415   -3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.5484   -3.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4676   -0.4175   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2842    0.8726    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2797    0.9762   -0.8665 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  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  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
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  1
  8 36  1  0
 11 37  1  0
 13 38  1  1
 14 39  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
 20 43  1  1
 22 44  1  0
 22 45  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
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Podophyllotoxin	ChEBI
9-HYDROXY-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-D][1,3]dioxol-6(5ah)-one	ChEBI
Condylox	ChEBI
Podophyllinic acid lactone	ChEBI
Podophyllotoxin 7	ChEBI
PPT	ChEBI
Podophyllotoxin	Kegg
ABBR PDX	Kegg
Podophyllinate lactone	Generator
Ardern brand OF podophyllotoxin	HMDB
Condyline	HMDB
Hamilton brand OF podophyllotoxin	HMDB
Oclassen brand OF podophyllotoxin	HMDB
Wartec	HMDB
CPH86	HMDB
Epipodophyllotoxin	HMDB
Fides ecopharma brand OF podophyllotoxin	HMDB
Paladin brand OF podophyllotoxin	HMDB
PODOCON-25	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	HMDB
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	HMDB
Warticon	HMDB
Newport brand OF podophyllotoxin	HMDB
Podofilm	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	HMDB
Wolff brand OF podophyllotoxin	HMDB
Canderm brand OF podophyllotoxin	HMDB
Paddock brand OF podophyllotoxin	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	HMDB
Stiefel brand OF podophyllotoxin	HMDB
Yamanouchi brand OF podophyllotoxin	HMDB
Podofilox	ChEBI

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4053 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

Traditional Name

(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1[C@@H]2[C@H](COC2=O)[C@@H](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/t13-,18+,19-,20-/m0/s1

InChI Key

YJGVMLPVUAXIQN-XVVDYKMHSA-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
Anthriscus sylvestris	KNApSAcK Database	22123792
Callitris drummondii	KNApSAcK Database	22123792
Condea verticillata	LOTUS Database	35616633
Diphylleia grayi	KNApSAcK Database	22123792
Diphylleia sinensis	KNApSAcK Database	22123792
Dysosma majorensis	KNApSAcK Database	22123792
Dysosma pleiantha	LOTUS Database	35616633
Dysosma veitchii	KNApSAcK Database	22123792
Dysosma versipellis	LOTUS Database	35616633
Eriope blanchetii	LOTUS Database	35616633
Hernandia ovigera	LOTUS Database	35616633
Hernandia sonora	LOTUS Database	35616633
Hugonia tomentosa	KNApSAcK Database	22123792
Hyptis verticillata	KNApSAcK Database	22123792
Juniperus chinensis	KNApSAcK Database	22123792
Juniperus phoenicea	KNApSAcK Database	22123792
Juniperus sabina	KNApSAcK Database	22123792
Juniperus thurifera	KNApSAcK Database	22123792
Juniperus thurifera var.africana	Plant	KNApSAcK
Juniperus virginiana	KNApSAcK Database	22123792
Linum album	KNApSAcK Database	22123792
Linum boissieri	KNApSAcK Database	22123792
Linum catharticum	KNApSAcK Database	22123792
Linum flavum	LOTUS Database	35616633
Linum flavum var. compactum	KNApSAcK Database	22123792
Linum mucronatum	LOTUS Database	35616633
Linum mucronatum ssp. armenum	KNApSAcK Database	22123792
Linum nodiflorum	LOTUS Database	35616633
Linum tauricum	LOTUS Database	35616633
Micranthemum umbrosum	KNApSAcK Database	22123792
Phialocephala fortinii	NPAtlas	16933860
Podophyllum emodi Wall	KNApSAcK Database	22123792
Podophyllum hexandrum	KNApSAcK Database	22123792
Podophyllum peltatum	KNApSAcK Database	22123792
Podophyllum pleianthum	KNApSAcK Database	22123792
Polygala polygama	KNApSAcK Database	22123792
Sinopodophyllum emodi	KNApSAcK Database	22123792
Sinopodophyllum emodi WALL.	Plant	KNApSAcK
Sinopodophyllum hexandrum	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	183.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	597.00 to 598.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	154.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.010	The Good Scents Company Information System

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	41.78 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

NPAtlas ID

NPA009289

HMDB ID

HMDB0015310

DrugBank ID

DB01179

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000610

Chemspider ID

10162

KEGG Compound ID

C10874

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Podophyllotoxin

METLIN ID

Not Available

PubChem Compound

10607

PDB ID

Not Available

ChEBI ID

50305

Good Scents ID

rw1275271

References

General References

Eyberger AL, Dondapati R, Porter JR: Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. J Nat Prod. 2006 Aug;69(8):1121-4. doi: 10.1021/np060174f. [PubMed:16933860 ]
Giorgi-Renault S: [4-Aza-2,3-didehydropodophyllotoxins: new lignan with antitumor activity obtained from one-step synthesis]. Ann Pharm Fr. 2005 Jan;63(1):63-8. doi: 10.1016/s0003-4509(05)82252-7. [PubMed:15803102 ]
Bhattacharyya D, Sinha R, Ghanta S, Chakraborty A, Hazra S, Chattopadhyay S: Proteins differentially expressed in elicited cell suspension culture of Podophyllum hexandrum with enhanced podophyllotoxin content. Proteome Sci. 2012 May 23;10(1):34. doi: 10.1186/1477-5956-10-34. [PubMed:22621772 ]
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 ]
Veloz RA, Cardoso-Taketa A, Villarreal ML: Production of podophyllotoxin from roots and plantlets of Hyptis suaveolens cultivated in vitro. Pharmacognosy Res. 2013 Apr;5(2):93-102. doi: 10.4103/0974-8490.110538. [PubMed:23798883 ]

Showing NP-Card for Podophyllotoxin (NP0006533)

MOL for NP0006533 (Podophyllotoxin)

3D MOL for NP0006533 (Podophyllotoxin)

3D SDF for NP0006533 (Podophyllotoxin)

3D-SDF for NP0006533 (Podophyllotoxin)

PDB for NP0006533 (Podophyllotoxin)

3D PDB for NP0006533 (Podophyllotoxin)

SMILES for NP0006533 (Podophyllotoxin)

INCHI for NP0006533 (Podophyllotoxin)

Structure for NP0006533 (Podophyllotoxin)

3D Structure for NP0006533 (Podophyllotoxin)