NP-MRD: Showing NP-Card for epipodophyllotoxin (NP0238289)

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Record Information

Version

2.0

Created at

2022-09-06 21:39:31 UTC

Updated at

2022-09-06 21:39:31 UTC

NP-MRD ID

NP0238289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epipodophyllotoxin

Description

Epipodophyllotoxin, also known as condylox or podofilm, 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). epipodophyllotoxin is found in Juniperus sabina and Podophyllum peltatum. epipodophyllotoxin was first documented in 2016 (PMID: 27687523). Based on a literature review a significant number of articles have been published on Epipodophyllotoxin (PMID: 36012385) (PMID: 35956979) (PMID: 34544406) (PMID: 34393438) (PMID: 33532438) (PMID: 33441065).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223392D          

 30 34  0  0  1  0            999 V2000
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  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
    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
    3.3523   -2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  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
    1.3683   -1.9354    0.0000 O   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
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  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
    6.7652   -1.9354    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
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    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
  6  5  1  6  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  6  0  0  0
  6 20  1  0  0  0  0
 15 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
  9 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
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -3.4698    2.0557    3.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8136    1.4783    1.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945    0.7978    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    0.6546    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -0.0114    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249   -0.0999    1.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6102    0.4271    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    1.7623   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    2.2827   -1.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    1.4825   -1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    0.1602   -1.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -0.3740   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8279   -0.1663 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9571   -2.0169    0.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -2.3907    0.6108 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0113   -3.5461    1.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9293   -3.5269    2.4854 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122   -2.2599    2.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -2.0179    3.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.4076    1.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9614    2.2430   -2.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739    3.6064   -2.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681    3.5502   -1.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0423   -0.5547   -0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -0.4074   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661   -0.9589   -2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475   -1.6534   -2.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    0.2602   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6268    0.4121   -0.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1132    1.4890   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    2.8910    3.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333    1.2737    3.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4338    2.4472    3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3159    1.1002    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    0.5794    2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    2.3720    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586   -0.4736   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7221   -2.3329   -1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -2.5305   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492   -2.7916    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -4.5030    1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791   -3.3189    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403   -1.2484    2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995    4.0797   -1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4648    4.1239   -3.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3743   -1.0835   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.9729   -3.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3987   -2.5029   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -2.0606   -3.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2182    1.3104   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0036    2.4694   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6426    1.5634   -2.2052 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  1
 20 43  1  1
 15 40  1  6
 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


  Mrv1652309062223392D          

 30 34  0  0  1  0            999 V2000
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  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
    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
    3.3523   -2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  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
    1.3683   -1.9354    0.0000 O   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
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  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
    6.7652   -1.9354    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
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    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
  6  5  1  6  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  6  0  0  0
  6 20  1  0  0  0  0
 15 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
  9 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
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238289

> <DATABASE_NAME>
NP-MRD

> <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-LGWHJFRWSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.643722776114544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11R,15R,16S)-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_LOGP>
1.6227982693333332

> <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>
103.905

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R,16S)-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

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.925   2.547   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   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  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -4.859   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  -2.367   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.590   4.087   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.924   4.857   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   15                                                  
CONECT   21   10   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    9                                                       
CONECT   24    5   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Condylox	MeSH
Podofilm	MeSH
Podofilox	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	MeSH
Wartec	MeSH
Warticon	MeSH
CPH86	MeSH
Condyline	MeSH
PODOCON-25	MeSH
Podophyllotoxin	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	MeSH

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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-LGWHJFRWSA-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
Juniperus sabina	LOTUS Database	35616633
Podophyllum peltatum	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

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000654

Chemspider ID

94835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epipodophyllotoxin

METLIN ID

Not Available

PubChem Compound

105111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Song YL, Liu SS, Yang J, Xie J, Zhou X, Wu ZB, Liu LW, Wang PY, Yang S: Discovery of Epipodophyllotoxin-Derived B(2) as Promising XooFtsZ Inhibitor for Controlling Bacterial Cell Division: Structure-Based Virtual Screening, Synthesis, and SAR Study. Int J Mol Sci. 2022 Aug 14;23(16):9119. doi: 10.3390/ijms23169119. [PubMed:36012385 ]
Xi W, Sun H, Bastow KF, Xiao Z, Lee KH: Identification of Novel 4'-O-Demethyl-epipodophyllotoxin Derivatives as Antitumor Agents Targeting Topoisomerase II. Molecules. 2022 Aug 7;27(15):5029. doi: 10.3390/molecules27155029. [PubMed:35956979 ]
Decembrino D, Raffaele A, Knofel R, Girhard M, Urlacher VB: Synthesis of (-)-deoxypodophyllotoxin and (-)-epipodophyllotoxin via a multi-enzyme cascade in E. coli. Microb Cell Fact. 2021 Sep 20;20(1):183. doi: 10.1186/s12934-021-01673-5. [PubMed:34544406 ]
Fathima JS, Selvaraj J, Sivabalan V, Rekha UV, Ponnulakshmi R, Vishnupriya V, Kullappan M, Sreekandan RN, Mohan SK: Molecular docking of alkaloid compounds with the matrix metalloproteinase 2. Bioinformation. 2021 Jan 31;17(1):206-211. doi: 10.6026/97320630017206. eCollection 2021. [PubMed:34393438 ]
Sneha LM, Arockia J, Suman FR, Khethan V: Secondary acute myeloid leukemia in a child treated for retinoblastoma: A case report with review of literature. J Family Med Prim Care. 2020 Nov 30;9(11):5796-5798. doi: 10.4103/jfmpc.jfmpc_1538_20. eCollection 2020 Nov. [PubMed:33532438 ]
Guo Q, Jiang E: Recent Advances in the Application of Podophyllotoxin Derivatives to Fight Against Multidrug-Resistant Cancer Cells. Curr Top Med Chem. 2021;21(19):1712-1724. doi: 10.2174/1568026621666210113163327. [PubMed:33441065 ]
Xiao J, Gao M, Sun Z, Diao Q, Wang P, Gao F: Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020). Eur J Med Chem. 2020 Dec 15;208:112830. doi: 10.1016/j.ejmech.2020.112830. Epub 2020 Sep 12. [PubMed:32992133 ]
Boye P, Floch F, Serres F, Segaoula Z, Hordeaux J, Pascal Q, Coste V, Courapied S, Bouchaert E, Rybicka A, Mazuy C, Marescaux L, Geeraert K, Fournel-Fleury C, Duhamel A, Machuron F, Ferre P, Petain A, Guilbaud N, Tierny D, Gomes B: Randomized, double-blind trial of F14512, a polyamine-vectorized anticancer drug, compared with etoposide phosphate, in dogs with naturally occurring lymphoma. Oncotarget. 2020 Feb 18;11(7):671-686. doi: 10.18632/oncotarget.27461. eCollection 2020 Feb 18. [PubMed:32133044 ]
Alliot J, Theodorou I, Duconge F, Gravel E, Doris E: Polyamine transport system-targeted nanometric micelles assembled from epipodophyllotoxin-amphiphiles. Chem Commun (Camb). 2019 Dec 10;55(99):14968-14971. doi: 10.1039/c9cc07883e. [PubMed:31776519 ]
Alliot J, Theodorou I, Nguyen DV, Forier C, Duconge F, Gravel E, Doris E: Tumor targeted micellar nanocarriers assembled from epipodophyllotoxin-based amphiphiles. Nanoscale. 2019 May 16;11(19):9756-9759. doi: 10.1039/c9nr01068h. [PubMed:31066425 ]
Che ZP, Tian YE, Liu SM, Jiang J, Hu M, Chen GQ: Stereoselective synthesis of 4beta-acyloxypodophyllotoxin derivatives as insecticidal agents. J Asian Nat Prod Res. 2019 Oct;21(10):1028-1041. doi: 10.1080/10286020.2018.1490275. Epub 2018 Jul 5. [PubMed:29974799 ]
Yang YJ, Qi SN, Shi RY, Yao J, Wang LS, Yuan HQ, Jing YX: Induction of apoptotic DNA fragmentation mediated by mitochondrial pathway with caspase-3-dependent BID cleavage in human gastric cancer cells by a new nitroxyl spin-labeled derivative of podophyllotoxin. Biomed Pharmacother. 2017 Jun;90:131-138. doi: 10.1016/j.biopha.2017.03.048. Epub 2017 Mar 26. [PubMed:28347917 ]
Hua F, Shang S, Hu ZW: Seeking new anti-cancer agents from autophagy-regulating natural products. J Asian Nat Prod Res. 2017 Apr;19(4):305-313. doi: 10.1080/10286020.2017.1304385. Epub 2017 Mar 28. [PubMed:28347180 ]
Casagranda L, Oriol M, Freycon F, Frappaz D, Bertrand Y, Bergeron C, Plantaz D, Stephan JL, Freycon C, Gomez F, Berger C, Trombert-Paviot B: Second malignant neoplasm following childhood cancer: A nested case-control study of a recent cohort (1987-2004) from the Childhood Cancer Registry of the Rhone-Alpes region in France. Pediatr Hematol Oncol. 2016 Sep;33(6):371-382. doi: 10.1080/08880018.2016.1214653. Epub 2016 Sep 29. [PubMed:27687523 ]
LOTUS database [Link]

Showing NP-Card for epipodophyllotoxin (NP0238289)

MOL for NP0238289 (epipodophyllotoxin)

3D MOL for NP0238289 (epipodophyllotoxin)

3D SDF for NP0238289 (epipodophyllotoxin)

3D-SDF for NP0238289 (epipodophyllotoxin)

PDB for NP0238289 (epipodophyllotoxin)

3D PDB for NP0238289 (epipodophyllotoxin)

SMILES for NP0238289 (epipodophyllotoxin)

INCHI for NP0238289 (epipodophyllotoxin)

Structure for NP0238289 (epipodophyllotoxin)

3D Structure for NP0238289 (epipodophyllotoxin)