NP-MRD: Showing NP-Card for Deoxypodophyllotoxin (NP0137236)

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Record Information

Version

2.0

Created at

2022-05-30 16:46:09 UTC

Updated at

2026-02-17 00:02:09 UTC

NP-MRD ID

NP0137236

Natural Product DOI

https://doi.org/10.57994/7322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxypodophyllotoxin

Description

Isoanthricin belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Deoxypodophyllotoxin is found in Anemone cernua, Anthriscus sylvestris, Austrobaileya scandens, Bursera permollis, Callitris columellaris, Cicuta maculata, Dysosma versipellis, Hernandia ovigera, Hernandia sonora, Illigera luzonensis, Juniperus rigida, Juniperus sabina, Juniperus thurifera, Juniperus virginiana, Linum album, Macrococculus pomiferus, Platycladus orientalis, Podolepis rugata, Podophyllum peltatum, Sinopodophyllum hexandrum, Tetraclinis articulata, Thuja occidentalis and Thujopsis dolabrata. Deoxypodophyllotoxin was first documented in 1979 (PMID: 423203). Isoanthricin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191517272D          

 29 33  0  0  0  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 13 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
    1.8179    2.9614   -2.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580    2.0835   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    0.9107   -0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647    0.4458   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6303   -0.7365   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653   -1.2293   -0.1514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6430   -0.2853    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969   -0.1227    1.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.7525    2.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2467    1.4657    1.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864    1.2967    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5868    0.4213   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7374    0.2287   -1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054   -1.2644   -1.7744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7697   -1.6299   -3.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5036   -1.1446   -3.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.3784   -2.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -1.2664   -2.8882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -1.7407   -1.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9130    2.2662    2.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    2.2322    4.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866    1.1205    4.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111   -1.4783    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -1.0563    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9573   -1.7894    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -2.9903    1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160    0.1371   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5567    0.5422   -0.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976    1.3658    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009    3.4011   -3.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615    2.4290   -2.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3900    3.7644   -1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965    1.0290   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7429   -2.1433    0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.6982    2.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1215    1.8431    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7331    0.5764   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985    0.7465   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839   -1.7635   -1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -2.7318   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6013   -1.1906   -3.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4116   -2.8735   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119    2.0571    4.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7100    3.1845    4.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041   -2.4231    0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -3.5223    2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -3.6826    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -2.8248    2.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490    2.4305    0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0852    1.2050    1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    1.0693    1.7813 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 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  2  0
 27 28  1  0
 28 29  1  0
  5  6  1  0
  6 19  1  0
 19 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 22  1  0
 22 21  1  0
 21 20  1  0
  9  8  1  0
  8  7  2  0
 27  3  1  0
  7  6  1  0
 17 19  1  0
  7 12  1  0
 20 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
 23 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
 29 49  1  0
 29 50  1  0
 29 51  1  0
  6 34  1  1
 19 42  1  1
 14 39  1  1
 15 40  1  0
 15 41  1  0
 13 37  1  0
 13 38  1  0
 11 36  1  0
 21 43  1  0
 21 44  1  0
  8 35  1  0
M  END


  Mrv1533004191517272D          

 29 33  0  0  0  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 13 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)CC2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3

> <INCHI_KEY>
ZGLXUQQMLLIKAN-UHFFFAOYSA-N

> <FORMULA>
C22H22O7

> <MOLECULAR_WEIGHT>
398.411

> <EXACT_MASS>
398.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.96019701631547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.812052609333333

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.267886551830654

> <JCHEM_POLAR_SURFACE_AREA>
72.45

> <JCHEM_REFRACTIVITY>
102.4883

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       3.590 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   29                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   13   21                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Isodeoxypodophyllotoxin	MeSH
Deoxypodophyllotoxin, (5R-(5alpha,5abeta,8aalpha))-isomer	MeSH
Deoxypodophyllotoxin, (5alpha,5aalpha,8aalpha)-(+-)-isomer	MeSH
Deoxypodophyllotoxin, (5alpha,5aalpha,8abeta)-(+-)-isomer	MeSH
Deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8abeta))-isomer	MeSH
Deoxypicropodophyllin	MeSH
Deoxypodophyllotoxin, (5R-(5alpha,5abeta,8abeta))-isomer	MeSH
Deoxypodophyllotoxin	MeSH
Deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8aalpha))-isomer	MeSH

Chemical Formula

C₂₂H₂₂O₇

Average Mass

398.4110 Da

Monoisotopic Mass

398.13655 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)CC2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3

InChI Key

ZGLXUQQMLLIKAN-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 270.0, Benzene-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 360.0, Chloroform-d, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anemone cernua	LOTUS Database	35616633
Anthriscus sylvestris	LOTUS Database	35616633
Austrobaileya scandens	LOTUS Database	35616633
Austrocedrus Austrocedrus chilensis		Not Available
Austrocedrus Austrocedrus chilensis		Not Available
Bursera permollis	LOTUS Database	35616633
Callitris columellaris	LOTUS Database	35616633
Cicuta maculata	LOTUS Database	35616633
Dysosma versipellis	LOTUS Database	35616633
Hernandia ovigera	LOTUS Database	35616633
Hernandia sonora	LOTUS Database	35616633
Illigera luzonensis	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Juniperus virginiana	LOTUS Database	35616633
Linum album	LOTUS Database	35616633
Macrococculus pomiferus	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Podolepis rugata	LOTUS Database	35616633
Podophyllum peltatum	LOTUS Database	35616633
Sinopodophyllum hexandrum	LOTUS Database	35616633
Tetraclinis articulata	LOTUS Database	35616633
Thuja occidentalis	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a lignan (CPD-8958 )

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	3.23	ALOGPS
logP	2.81	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.49 m³·mol⁻¹	ChemAxon
Polarizability	40.96 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2203

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Deoxypodophyllotoxin (NP0137236)

MOL for NP0137236 (Deoxypodophyllotoxin)

3D MOL for NP0137236 (Deoxypodophyllotoxin)

3D SDF for NP0137236 (Deoxypodophyllotoxin)

3D-SDF for NP0137236 (Deoxypodophyllotoxin)

PDB for NP0137236 (Deoxypodophyllotoxin)

3D PDB for NP0137236 (Deoxypodophyllotoxin)

SMILES for NP0137236 (Deoxypodophyllotoxin)

INCHI for NP0137236 (Deoxypodophyllotoxin)

Structure for NP0137236 (Deoxypodophyllotoxin)

3D Structure for NP0137236 (Deoxypodophyllotoxin)