NP-MRD: Showing NP-Card for epipodophyllotoxins (NP0242440)

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Record Information

Version

2.0

Created at

2022-09-07 02:45:27 UTC

Updated at

2022-09-07 02:45:28 UTC

NP-MRD ID

NP0242440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epipodophyllotoxins

Description

Picropodophyllin 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). Picropodophyllin is an extremely weak basic (essentially neutral) compound (based on its pKa). epipodophyllotoxins is found in Anthriscus sylvestris, Hernandia sonora, Juniperus sabina, Juniperus thurifera and Podophyllum peltatum. epipodophyllotoxins was first documented in 2010 (PMID: 20150364). An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents (PMID: 21251888) (PMID: 21330319).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310211602212D          

 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
    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
    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
    1.9233    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   -1.1104    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
    2.6378   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  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
    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
    3.3523   -3.5854    0.0000 O   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
    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
  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  5  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  1  0  0  0
 20 27  1  6  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -3.7247   -1.8905    2.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0428   -0.8493    1.4929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526   -0.4228    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8135   -1.0140    0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7999   -0.6480   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362   -1.3212   -0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4654   -0.5860    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1842   -0.4677    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    0.2059    2.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    0.7677    2.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    0.6495    1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.0322    0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9977   -0.0861   -1.2962 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2121    1.2104   -1.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -0.8323   -2.1838 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9106   -1.8611   -2.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -2.9761   -2.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7038   -3.0277   -1.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064   -4.0363   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -1.6704   -1.5738 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8333    1.3886    3.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    1.4925    4.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    0.4520    4.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    0.3689   -1.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    0.9770   -1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.9813   -2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456    2.5248   -3.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299    0.5835   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5665    1.1912   -0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044    2.3223    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8700   -1.5779    3.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6238   -2.1457    2.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -2.7656    1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -1.8047    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520   -2.3013    0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837   -0.9273    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3257    1.0976    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0307   -0.5476   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    1.5844   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.1484   -2.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666   -2.0511   -3.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.5004   -3.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -1.8049   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424    1.3607    5.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4206    2.4811    4.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    0.6934   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745    2.8639   -3.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952    3.4009   -2.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    1.7955   -3.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5579    2.0241    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4769    3.0023   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130    2.8769    0.7700 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  6
 15 40  1  6
 16 41  1  0
 16 42  1  0
 13 38  1  1
 14 39  1  0
 11 37  1  0
 22 44  1  0
 22 45  1  0
  8 36  1  0
M  END


  Mrv1652310211602212D          

 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
    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
    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
    1.9233    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   -1.1104    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
    2.6378   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  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
    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
    3.3523   -3.5854    0.0000 O   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
    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
  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  5  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  1  0  0  0
 20 27  1  6  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242440

> <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-HAEOHBJNSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.682572164218456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,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,11S,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

$$$$

HEADER    PROTEIN                                 21-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-16         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       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.924   4.857   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590   4.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   22                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   13   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   21                                                       
CONECT   27   20                                                            
CONECT   28   17   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   16                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Picropodophyllin	ChEBI
Cyclolignan PPP	MeSH
picro-Podophyllin	MeSH

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

(10R,11S,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,11S,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-HAEOHBJNSA-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
Hernandia sonora	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Juniperus thurifera	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

lignan (CHEBI:75251 )
furonaphthodioxole (CHEBI:75251 )

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	41.68 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

DB12802

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002619

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

72435

PDB ID

Not Available

ChEBI ID

75251

Good Scents ID

Not Available

References

General References

Yin S, Girnita A, Stromberg T, Khan Z, Andersson S, Zheng H, Ericsson C, Axelson M, Nister M, Larsson O, Ekstrom TJ, Girnita L: Targeting the insulin-like growth factor-1 receptor by picropodophyllin as a treatment option for glioblastoma. Neuro Oncol. 2010 Jan;12(1):19-27. doi: 10.1093/neuonc/nop008. Epub 2009 Oct 20. [PubMed:20150364 ]
Ronquist-Nii Y, Eksborg S, Axelson M, Harmenberg J, Ekman S, Bergqvist M, Beck O: Determination of picropodophyllin and its isomer podophyllotoxin in human serum samples with electrospray ionization of hexylamine adducts by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Feb 15;879(5-6):326-34. doi: 10.1016/j.jchromb.2010.12.017. Epub 2010 Dec 28. [PubMed:21251888 ]
Vishwamitra D, Shi P, Wilson D, Manshouri R, Vega F, Schlette EJ, Amin HM: Expression and effects of inhibition of type I insulin-like growth factor receptor tyrosine kinase in mantle cell lymphoma. Haematologica. 2011 Jun;96(6):871-80. doi: 10.3324/haematol.2010.031567. Epub 2011 Feb 17. [PubMed:21330319 ]
LOTUS database [Link]

Showing NP-Card for epipodophyllotoxins (NP0242440)

MOL for NP0242440 (epipodophyllotoxins)

3D MOL for NP0242440 (epipodophyllotoxins)

3D SDF for NP0242440 (epipodophyllotoxins)

3D-SDF for NP0242440 (epipodophyllotoxins)

PDB for NP0242440 (epipodophyllotoxins)

3D PDB for NP0242440 (epipodophyllotoxins)

SMILES for NP0242440 (epipodophyllotoxins)

INCHI for NP0242440 (epipodophyllotoxins)

Structure for NP0242440 (epipodophyllotoxins)

3D Structure for NP0242440 (epipodophyllotoxins)