NP-MRD: Showing NP-Card for podophyllotoxone (NP0040823)

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Record Information

Version

2.0

Created at

2021-06-20 22:53:06 UTC

Updated at

2021-06-30 00:14:57 UTC

NP-MRD ID

NP0040823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

podophyllotoxone

Provided By

JEOL Database JEOL Logo

Description

(11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-triene-10,14-dione 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. podophyllotoxone is found in Anthriscus sylvestris, Diphylleia grayi and Dysosma versipellis. podophyllotoxone was first documented in 2011 (Hendrawati, O., et al.). Based on a literature review very few articles have been published on (11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-triene-10,14-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100533D          

 50 54  0  0  0  0            999 V2000
    4.3457    2.8808    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    2.3138   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    2.6210   -0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    1.5458   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1251    1.7067   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    0.5599   -0.2401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5442   -0.8180    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.1408    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671   -2.3865    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -3.3051    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0364   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.7790   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -1.4587   -2.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -2.3017   -3.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -0.0318   -2.6438 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.3538    1.6113   -2.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    2.5314   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9297   -4.1712    2.7321 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4187   -2.8546    3.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.9884    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    4.0862    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    5.3632    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    5.6292    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    3.8973    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    4.9732    0.2502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    5.6373   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2060    2.2102    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    3.8470    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    2.9711    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9393    4.9637   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783    6.4611   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 20  1  0  0  0  0
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  7  6  1  0  0  0  0
 13 14  2  0  0  0  0
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  6 35  1  1  0  0  0
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 16 39  1  0  0  0  0
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 22 42  1  0  0  0  0
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  4 34  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
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 30 48  1  0  0  0  0
 30 49  1  0  0  0  0
 30 50  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
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    0.9636   -4.4649    1.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297   -4.1712    2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 13  1  0
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M  END


  Mrv1652306212100533D          

 50 54  0  0  0  0            999 V2000
    4.3457    2.8808    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    2.3138   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4776   -3.3051    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0364   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6802    6.7049    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    5.3673   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    6.0616   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    4.9637   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783    6.4611   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 20  1  0  0  0  0
 15 13  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
 23  9  1  0  0  0  0
 15 20  1  0  0  0  0
  6  5  1  0  0  0  0
 12 11  1  0  0  0  0
  5 24  1  0  0  0  0
 12  7  2  0  0  0  0
 24 25  2  0  0  0  0
 25 28  1  0  0  0  0
 10 11  2  0  0  0  0
 28  3  2  0  0  0  0
  9  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 20 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 17  1  0  0  0  0
 28 29  1  0  0  0  0
 17 16  1  0  0  0  0
 25 26  1  0  0  0  0
 15 16  1  0  0  0  0
  3  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
  8  7  1  0  0  0  0
 26 27  1  0  0  0  0
 12 13  1  0  0  0  0
 29 30  1  0  0  0  0
  7  6  1  0  0  0  0
 13 14  2  0  0  0  0
  8 36  1  0  0  0  0
 11 37  1  0  0  0  0
  6 35  1  1  0  0  0
 15 38  1  6  0  0  0
 20 41  1  1  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 24 44  1  0  0  0  0
  4 34  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 27 45  1  0  0  0  0
 27 46  1  0  0  0  0
 27 47  1  0  0  0  0
 30 48  1  0  0  0  0
 30 49  1  0  0  0  0
 30 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2OC([H])([H])OC2=C([H])C2=C1C(=O)[C@@]1([H])C([H])([H])OC(=O)[C@]1([H])[C@]2([H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O8/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/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19-/m0/s1

> <INCHI_KEY>
ISCQYPPCSYRZOT-BKTGTZMESA-N

> <FORMULA>
C22H20O8

> <MOLECULAR_WEIGHT>
412.394

> <EXACT_MASS>
412.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.1472868398886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-triene-10,14-dione

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.0015981676666663

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.507290041152187

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271039017840125

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
103.2237

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-triene-10,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    4.3457    2.8808    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    2.3138   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    2.6210   -0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    1.5458   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1251    1.7067   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    0.5599   -0.2401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5442   -0.8180    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.1408    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671   -2.3865    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -3.3051    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0364   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.7790   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -1.4587   -2.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -2.3017   -3.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -0.0318   -2.6438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4846    0.2299   -3.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070    1.4475   -3.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538    1.6113   -2.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    2.5314   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557    0.4285   -1.6220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9636   -4.4649    1.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297   -4.1712    2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4187   -2.8546    3.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.9884    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    4.0862    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    5.3632    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    5.6292    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    3.8973    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    4.9732    0.2502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    5.6373   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2060    2.2102    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    3.8470    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    2.9711    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    0.5762   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    0.7470    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.4382    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -3.7760   -1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.5683   -2.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    0.3884   -4.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979   -0.5570   -4.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.3028   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -4.2513    3.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957   -4.9139    3.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    3.1139    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    5.1148    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802    6.7049    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    5.3673   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    6.0616   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    4.9637   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783    6.4611   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 20  1  0
 15 13  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 23  9  1  0
 15 20  1  0
  6  5  1  0
 12 11  1  0
  5 24  1  0
 12  7  2  0
 24 25  2  0
 25 28  1  0
 10 11  2  0
 28  3  2  0
  9  8  2  0
  3  4  1  0
  4  5  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 28 29  1  0
 17 16  1  0
 25 26  1  0
 15 16  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
  8  7  1  0
 26 27  1  0
 12 13  1  0
 29 30  1  0
  7  6  1  0
 13 14  2  0
  8 36  1  0
 11 37  1  0
  6 35  1  1
 15 38  1  6
 20 41  1  1
 16 39  1  0
 16 40  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
 30 48  1  0
 30 49  1  0
 30 50  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       4.346   2.881   0.641  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.459   2.314  -0.322  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.139   2.621  -0.118  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.258   1.546  -0.270  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.125   1.707  -0.090  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.121   0.560  -0.240  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.544  -0.818   0.122  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.343  -1.141   1.476  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.167  -2.386   1.778  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.478  -3.305   0.802  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.302  -3.036  -0.538  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.208  -1.779  -0.884  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.395  -1.459  -2.335  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.225  -2.302  -3.206  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.744  -0.032  -2.644  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.485   0.230  -3.926  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.207   1.448  -3.667  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.354   1.611  -2.313  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.955   2.531  -1.787  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.756   0.429  -1.622  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.964  -4.465   1.320  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.930  -4.171   2.732  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.419  -2.855   3.029  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.606   2.988   0.240  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.256   4.086   0.353  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.146   5.363   0.652  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.543   5.629   0.627  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.633   3.897   0.154  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.483   4.973   0.250  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.566   5.637  -1.012  0.00  0.00           C+0
HETATM   31  H   UNK     0       5.206   2.210   0.732  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.719   3.847   0.290  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.891   2.971   1.634  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.686   0.576  -0.514  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.938   0.747   0.473  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.574  -0.438   2.271  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.558  -3.776  -1.290  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.173   0.568  -2.639  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.803   0.388  -4.767  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.198  -0.557  -4.194  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.579  -0.303  -1.552  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.947  -4.251   3.132  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.296  -4.914   3.230  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.674   3.114   0.400  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.054   5.115   1.447  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.680   6.705   0.774  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.982   5.367  -0.342  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.600   6.062  -1.307  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.939   4.964  -1.791  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.278   6.461  -0.909  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3   28    4    2                                                  
CONECT    4    3    5   34                                                  
CONECT    5    6   24    4                                                  
CONECT    6   20    5    7   35                                             
CONECT    7   12    8    6                                                  
CONECT    8    9    7   36                                                  
CONECT    9   23    8   10                                                  
CONECT   10   21   11    9                                                  
CONECT   11   12   10   37                                                  
CONECT   12   11    7   13                                                  
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   13   20   16   38                                             
CONECT   16   17   15   39   40                                             
CONECT   17   18   16                                                       
CONECT   18   20   19   17                                                  
CONECT   19   18                                                            
CONECT   20    6   15   18   41                                             
CONECT   21   10   22                                                       
CONECT   22   21   23   42   43                                             
CONECT   23   22    9                                                       
CONECT   24    5   25   44                                                  
CONECT   25   24   28   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   45   46   47                                             
CONECT   28   25    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   48   49   50                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37   11                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   20                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   27                                                            
CONECT   46   27                                                            
CONECT   47   27                                                            
CONECT   48   30                                                            
CONECT   49   30                                                            
CONECT   50   30                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

RDKit          3D

50 54  0  0  0  0  0  0  0  0999 V2000
    4.3457    2.8808    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    2.3138   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    2.6210   -0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    1.5458   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1251    1.7067   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214    0.5599   -0.2401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5442   -0.8180    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.1408    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671   -2.3865    1.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -3.3051    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -3.0364   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -1.7790   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -1.4587   -2.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -2.3017   -3.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -0.0318   -2.6438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4846    0.2299   -3.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070    1.4475   -3.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3538    1.6113   -2.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    2.5314   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557    0.4285   -1.6220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9636   -4.4649    1.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297   -4.1712    2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4187   -2.8546    3.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056    2.9884    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    4.0862    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    5.3632    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431    5.6292    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332    3.8973    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832    4.9732    0.2502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    5.6373   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2060    2.2102    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    3.8470    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    2.9711    1.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    0.5762   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    0.7470    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.4382    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -3.7760   -1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.5683   -2.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8033    0.3884   -4.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979   -0.5570   -4.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.3028   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -4.2513    3.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957   -4.9139    3.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    3.1139    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    5.1148    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802    6.7049    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    5.3673   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    6.0616   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    4.9637   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783    6.4611   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 20  1  0
 15 13  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 23  9  1  0
 15 20  1  0
  6  5  1  0
 12 11  1  0
  5 24  1  0
 12  7  2  0
 24 25  2  0
 25 28  1  0
 10 11  2  0
 28  3  2  0
  9  8  2  0
  3  4  1  0
  4  5  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 28 29  1  0
 17 16  1  0
 25 26  1  0
 15 16  1  0
  3  2  1  0
  9 10  1  0
  2  1  1  0
  8  7  1  0
 26 27  1  0
 12 13  1  0
 29 30  1  0
  7  6  1  0
 13 14  2  0
  8 36  1  0
 11 37  1  0
  6 35  1  1
 15 38  1  6
 20 41  1  1
 16 39  1  0
 16 40  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
 30 48  1  0
 30 49  1  0
 30 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₈

Average Mass

412.3940 Da

Monoisotopic Mass

412.11582 Da

IUPAC Name

(11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-triene-10,14-dione

Traditional Name

(11R,15R,16R)-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-triene-10,14-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC([H])([H])OC2=C([H])C2=C1C(=O)[C@@]1([H])C([H])([H])OC(=O)[C@]1([H])[C@]2([H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C22H20O8/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/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19-/m0/s1

InChI Key

ISCQYPPCSYRZOT-BKTGTZMESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthriscus sylvestris	JEOL database	Hendrawati, O., et al, Phytochem. 72, 2172 (2011)
Diphylleia grayi	LOTUS Database	35616633
Diphylleia sinensis	KNApSAcK Database	22123792
Dysosma majorensis	KNApSAcK Database	22123792
Dysosma pleiantha	KNApSAcK Database	22123792
Dysosma versipellis	LOTUS Database	35616633
Juniperus thurifera	KNApSAcK Database	22123792
Podophyllum emodii	KNApSAcK Database	22123792
Podophyllum hexandrum	KNApSAcK Database	22123792
Podophyllum peltatum	KNApSAcK Database	22123792
Podophyllum pleianthum	KNApSAcK Database	22123792
Sinopodophyllum hexandrum	KNApSAcK Database	22123792

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
Phenol ether
Anisole
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Ketone
Carboxylic acid ester
Lactone
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

lactone (CHEBI:8281 )
lignan (CHEBI:8281 )
Lignans (C10875 )

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	2.55	ALOGPS
logP	2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.51	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.22 m³·mol⁻¹	ChemAxon
Polarizability	41.15 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

C00002620

Chemspider ID

391315

KEGG Compound ID

C10875

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443014

PDB ID

Not Available

ChEBI ID

8281

Good Scents ID

Not Available

References

General References

Hendrawati, O., et al. (2011). Hendrawati, O., et al, Phytochem. 72, 2172 (2011). Phytochem..

Showing NP-Card for podophyllotoxone (NP0040823)

MOL for NP0040823 (podophyllotoxone)

3D MOL for NP0040823 (podophyllotoxone)

3D SDF for NP0040823 (podophyllotoxone)

3D-SDF for NP0040823 (podophyllotoxone)

PDB for NP0040823 (podophyllotoxone)

3D PDB for NP0040823 (podophyllotoxone)

SMILES for NP0040823 (podophyllotoxone)

INCHI for NP0040823 (podophyllotoxone)

Structure for NP0040823 (podophyllotoxone)

3D Structure for NP0040823 (podophyllotoxone)