NP-MRD: Showing NP-Card for (10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0223769)

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Record Information

Version

2.0

Created at

2022-09-06 01:57:28 UTC

Updated at

2022-09-06 01:57:28 UTC

NP-MRD ID

NP0223769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Description

(10S,11R,15R,16R)-16-Hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-12-one belongs to the class of organic compounds known as podophyllotoxins. (10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one is found in Micranthemum umbrosum. 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) (10S,11R,15R,16R)-16-Hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-12-one is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 12021420082D          

 32 36  0  0  1  0            999 V2000
    4.7148    2.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563    1.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192   -2.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699   -2.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989   -1.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    1.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4410    1.2065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4410    0.3815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0120    1.2065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7266   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    0.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    1.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397   -0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613   -0.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -0.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699    0.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699   -1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -2.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -2.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989    1.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0134   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931    2.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442    0.9388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  6  0  0  0
  3 16  2  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  1  0  0  0  0
  5 27  1  0  0  0  0
  6 24  1  0  0  0  0
  6 28  1  0  0  0  0
  7 25  1  0  0  0  0
  7 29  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 31  1  6  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 10 32  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  1  1  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    2.4902   -2.3533   -2.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824   -1.3503   -2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -0.5852   -1.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335   -0.8131   -0.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -0.0912    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232   -0.4374    0.7528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5695    0.2341   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    1.3223   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515    1.8887   -1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6394    1.4023   -1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    0.3108   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8470   -0.2571    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265   -1.4405    0.9163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1160   -0.9299    1.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830   -2.0481    1.6109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0853   -3.5224    1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -3.7843    1.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0609   -2.8076    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027   -2.7814    1.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504   -1.8865    0.7000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5002    2.1431   -2.2196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    3.3129   -2.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105    2.9686   -2.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608    0.9018    1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510    1.1424    0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5993    2.1471    1.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054    2.8928    2.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527    0.4105   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7425    0.6721   -0.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0845    1.5985   -1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5363   -1.9041   -3.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -3.0609   -1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -2.8688   -3.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8862   -1.6228   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6637   -0.0835    1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818    1.7340   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9145   -0.0701   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -2.1927    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460   -0.6070    2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -1.5862    2.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263   -3.8402    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457   -4.0388    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145   -2.1706   -0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1045    4.1486   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0007    3.4907   -3.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111    1.4997    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5745    2.2350    3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705    3.5523    2.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    3.4916    1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355    1.4151   -2.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1815    1.6094   -1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    2.6097   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 28  2  0
 28 29  1  0
 29 30  1  0
 28 25  1  0
 25 26  1  0
 26 27  1  0
 25 24  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 20 15  1  0
 24  5  1  0
 12  7  1  0
 13 15  1  0
 23  9  1  0
 15 40  1  1
 16 41  1  0
 16 42  1  0
 20 43  1  6
  6 35  1  1
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 24 46  1  0
  8 36  1  0
 22 44  1  0
 22 45  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
M  END


  Mrv0541 12021420082D          

 32 36  0  0  1  0            999 V2000
    4.7148    2.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563    1.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192   -2.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699   -2.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989   -1.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    1.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4410    1.2065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4410    0.3815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0120    1.2065    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7266   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    0.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0490    1.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397   -0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613   -0.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -0.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699    0.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1555   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699   -1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -0.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -2.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -2.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2989    1.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0134   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931    2.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442    0.9388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  6  0  0  0
  3 16  2  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  1  0  0  0  0
  5 27  1  0  0  0  0
  6 24  1  0  0  0  0
  6 28  1  0  0  0  0
  7 25  1  0  0  0  0
  7 29  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 31  1  6  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 10 32  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  1  1  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0223769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])[C@@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O

> <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-KJYZGMDISA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.4053

> <EXACT_MASS>
414.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.004685220173286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S,11R,15R,16R)-16-hydroxy-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>
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>
(10S,11R,15R,16R)-16-hydroxy-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                                 02-DEC-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-DEC-14         0                                  
HETATM    1  O   UNK     0       8.801   4.678   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.289   3.022   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.932   2.962   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.262  -4.033   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.026  -2.742   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      10.957  -3.908   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.625   0.712   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.625  -2.368   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.956   3.022   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.290   2.252   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.290   0.712   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.622   2.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.956  -0.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.278   4.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.622   0.712   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.425   3.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.624  -0.058   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.981  -1.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.221  -0.068   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.598  -2.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.209  -1.672   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.957   0.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.624  -1.598   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.957  -2.368   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.291  -0.058   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.291  -1.598   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.676  -4.198   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.291  -4.678   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.625   2.252   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.958  -1.598   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       5.961   3.748   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.416   1.752   0.000  0.00  0.00           H+0
CONECT    1   14   16                                                       
CONECT    2   12                                                            
CONECT    3   16                                                            
CONECT    4   20   27                                                       
CONECT    5   21   27                                                       
CONECT    6   24   28                                                       
CONECT    7   25   29                                                       
CONECT    8   26   30                                                       
CONECT    9   10   12   14   31                                             
CONECT   10    9   11   16   32                                             
CONECT   11   10   13   17                                                  
CONECT   12    2    9   15                                                  
CONECT   13   11   15   18                                                  
CONECT   14    1    9                                                       
CONECT   15   12   13   19                                                  
CONECT   16    1    3   10                                                  
CONECT   17   11   22   23                                                  
CONECT   18   13   20                                                       
CONECT   19   15   21                                                       
CONECT   20    4   18   21                                                  
CONECT   21    5   19   20                                                  
CONECT   22   17   25                                                       
CONECT   23   17   24                                                       
CONECT   24    6   23   26                                                  
CONECT   25    7   22   26                                                  
CONECT   26    8   24   25                                                  
CONECT   27    4    5                                                       
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
Ardern brand OF podophyllotoxin	MeSH
CPH86	MeSH
Canderm brand OF podophyllotoxin	MeSH
Condylox	MeSH
Epipodophyllotoxin	MeSH
Fides ecopharma brand OF podophyllotoxin	MeSH
Hamilton brand OF podophyllotoxin	MeSH
Newport brand OF podophyllotoxin	MeSH
Oclassen brand OF podophyllotoxin	MeSH
Paddock brand OF podophyllotoxin	MeSH
Paladin brand OF podophyllotoxin	MeSH
PODOCON-25	MeSH
Podofilm	MeSH
Podophyllotoxin	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	MeSH
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	MeSH
Stiefel brand OF podophyllotoxin	MeSH
Wartec	MeSH
Warticon	MeSH
Wolff brand OF podophyllotoxin	MeSH
Yamanouchi brand OF podophyllotoxin	MeSH

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4053 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

(10S,11R,15R,16R)-16-hydroxy-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

(10S,11R,15R,16R)-16-hydroxy-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

[H][C@]12COC(=O)[C@]1([H])[C@@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O

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-KJYZGMDISA-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
Micranthemum umbrosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	42 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

11047943

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0223769)

MOL for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D MOL for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D SDF for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D-SDF for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

PDB for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D PDB for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

SMILES for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

INCHI for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

Structure for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D Structure for NP0223769 ((10s,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)