NP-MRD: Showing NP-Card for 4-Demethyl-podophyllotoxin (NP0051502)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:50:39 UTC

Updated at

2022-04-27 22:50:39 UTC

NP-MRD ID

NP0051502

Secondary Accession Numbers

NP0137774

Natural Product Identification

Common Name

4-Demethyl-podophyllotoxin

Description

4'-Demethylpodophyllotoxin 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). 4'-Demethylpodophyllotoxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4-Demethyl-podophyllotoxin is found in Achillea holosericea, Condea verticillata, Diphylleia grayi, Diphylleia sinensis, Dysosma difformis, Dysosma furfuracea, Dysosma guangxiensis, Dysosma majorensis, Dysosma pleiantha, Dysosma veitchii, Dysosma versipellis, Hyptis verticillata , Linum album, Podophyllum emodii, Podophyllum hexandrum , Podophyllum peltatum , Polygala polygama and Sinopodophyllum hexandrum. 4-Demethyl-podophyllotoxin was first documented in 2013 (PMID: 23418155). Based on a literature review a small amount of articles have been published on 4'-demethylpodophyllotoxin (PMID: 26323159) (PMID: 25834987) (PMID: 24122912).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200502D          

 29 33  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    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
    4.7812    1.9354    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
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    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    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   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
    3.3523    4.4104    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    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  6  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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    2.9058   -2.0545   -2.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -1.5407   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595   -0.6458   -0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -0.2351   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9861    0.6511   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    1.1150   -0.2046 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3842    0.2217    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2925    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396   -1.1316    2.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309   -1.4545    1.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4620   -0.9452    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802   -0.1167   -0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    0.4125   -1.4590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9486   -0.3075   -2.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6400    0.3736   -2.2273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7107    0.9380   -3.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    1.2653   -3.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    1.6060   -2.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710    1.9559   -2.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924    1.4533   -1.5757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7972   -2.2931    2.6534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521   -2.6375    3.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8533   -1.7696    3.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362    1.1141    1.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144    0.7396    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6785    1.2515    2.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017    2.1559    3.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6367   -0.1507    0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444   -0.5099    0.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4497   -2.9203   -2.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120   -1.3032   -3.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -2.4437   -2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1213   -0.6404   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    2.0854    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396   -0.0722    2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4214   -1.2487    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122    1.4807   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -0.8279   -2.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1781   -0.6102   -2.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616    1.8945   -3.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0676    0.2313   -4.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299    2.3730   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -2.3937    4.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -3.7055    3.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    1.8204    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402    2.9748    2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    1.6656    4.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370    2.6252    3.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.1538    1.5937 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
  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  7  2  0
  7  8  1  0
  8  9  2  0
  9 23  1  0
 23 22  1  0
 22 21  1  0
 21 10  1  0
 10 11  2  0
 28  3  1  0
  7  6  1  0
 10  9  1  0
 18 20  1  0
 11 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
 24 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 29 49  1  0
  6 34  1  1
 20 42  1  1
 15 39  1  6
 16 40  1  0
 16 41  1  0
 13 37  1  1
 14 38  1  0
  8 35  1  0
 22 43  1  0
 22 44  1  0
 11 36  1  0
M  END


  Mrv1652304282200502D          

 29 33  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    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
    4.7812    1.9354    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
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    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    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   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
    3.3523    4.4104    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    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  6  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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@H]1[C@@H]2[C@H](COC2=O)[C@@H](O)C2=C1C=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19-/m0/s1

> <INCHI_KEY>
YVCVYCSAAZQOJI-BTINSWFASA-N

> <FORMULA>
C21H20O8

> <MOLECULAR_WEIGHT>
400.383

> <EXACT_MASS>
400.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.78108091683238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.4769042133333325

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.015760306573444

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.330432884682493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.229310382900084

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
99.4227

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.390   4.089   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.295   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.390   1.597   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924  10.543   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.257   9.003   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.257  10.543   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11   29                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12    1   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16   24                                                       
CONECT   24   23                                                            
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   11                                                       
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
4'-O-Demethylpodophyllotoxin	ChEBI
O(4')-Demethylpodophyllotoxin	ChEBI

Chemical Formula

C₂₁H₂₀O₈

Average Mass

400.3830 Da

Monoisotopic Mass

400.11582 Da

IUPAC Name

(10R,11R,15R,16R)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-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-(4-hydroxy-3,5-dimethoxyphenyl)-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)=C1O)[C@H]1[C@@H]2[C@H](COC2=O)[C@@H](O)C2=C1C=C1OCOC1=C2

InChI Identifier

InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19-/m0/s1

InChI Key

YVCVYCSAAZQOJI-BTINSWFASA-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
Achillea holosericea	Plant	KNApSAcK
Condea verticillata	LOTUS Database	35616633
Diphylleia grayi	LOTUS Database	35616633
Diphylleia sinensis	Plant	KNApSAcK
Dysosma difformis	Plant	KNApSAcK
Dysosma furfuracea	Plant	KNApSAcK
Dysosma guangxiensis	Plant	KNApSAcK
Dysosma majorensis	Plant	KNApSAcK
Dysosma pleiantha	Plant	KNApSAcK
Dysosma veitchii	Plant	KNApSAcK
Dysosma versipellis	Plant	KNApSAcK
Hyptis verticillata	Plant	KNApSAcK
Linum album	Plant	KNApSAcK
Podophyllum emodii	Plant	KNApSAcK
Podophyllum hexandrum	Plant	KNApSAcK
Podophyllum peltatum	Plant	KNApSAcK
Polygala polygama	Plant	KNApSAcK
Sinopodophyllum hexandrum	Plant	KNApSAcK

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
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Tetralin
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:1730 )
phenols (CHEBI:1730 )
furonaphthodioxole (CHEBI:1730 )
Lignans (C10553 )

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	1.84	ALOGPS
logP	1.48	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.42 m³·mol⁻¹	ChemAxon
Polarizability	39.78 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002595

Chemspider ID

109366

KEGG Compound ID

C10553

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122667

PDB ID

Not Available

ChEBI ID

1730

Good Scents ID

Not Available

References

General References

Li YL, Ning Y, Xu WH, Zhou GY: [Dynamic study on two lignans contents in different parts of Sinopodophyllum hexandrum]. Zhongguo Zhong Yao Za Zhi. 2015 May;40(9):1837-41. [PubMed:26323159 ]
Glaser J, Schultheis M, Moll H, Hazra B, Holzgrabe U: Antileishmanial and cytotoxic compounds from Valeriana wallichii and identification of a novel nepetolactone derivative. Molecules. 2015 Apr 1;20(4):5740-53. doi: 10.3390/molecules20045740. [PubMed:25834987 ]
Zhao C, Zhang N, He W, Li R, Shi D, Pang L, Dong N, Xu H, Ji H: Simultaneous determination of three major lignans in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Diphylleia sinensis extract. Biomed Chromatogr. 2014 Apr;28(4):463-7. doi: 10.1002/bmc.3066. Epub 2013 Oct 14. [PubMed:24122912 ]
Yang Z, Liu X, Wang K, Cao X, Wu S: Novel linear and step-gradient counter-current chromatography for bio-guided isolation and purification of cytotoxic podophyllotoxins from Dysosma versipellis (Hance). J Sep Sci. 2013 Mar;36(6):1022-8. doi: 10.1002/jssc.201201038. Epub 2013 Feb 18. [PubMed:23418155 ]

Showing NP-Card for 4-Demethyl-podophyllotoxin (NP0051502)

MOL for NP0051502 (4-Demethyl-podophyllotoxin)

3D MOL for NP0051502 (4-Demethyl-podophyllotoxin)

3D SDF for NP0051502 (4-Demethyl-podophyllotoxin)

3D-SDF for NP0051502 (4-Demethyl-podophyllotoxin)

PDB for NP0051502 (4-Demethyl-podophyllotoxin)

3D PDB for NP0051502 (4-Demethyl-podophyllotoxin)

SMILES for NP0051502 (4-Demethyl-podophyllotoxin)

INCHI for NP0051502 (4-Demethyl-podophyllotoxin)

Structure for NP0051502 (4-Demethyl-podophyllotoxin)

3D Structure for NP0051502 (4-Demethyl-podophyllotoxin)