NP-MRD: Showing NP-Card for (10r,15r)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0143692)

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Record Information

Version

2.0

Created at

2022-09-01 22:31:08 UTC

Updated at

2022-09-01 22:31:08 UTC

NP-MRD ID

NP0143692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r,15r)-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

Desoxypodophyllotoxin 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. (10r,15r)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one was first documented in 2014 (PMID: 24188177). Based on a literature review a small amount of articles have been published on Desoxypodophyllotoxin (PMID: 30577489) (PMID: 26091020) (PMID: 32891861) (PMID: 28082643).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200312D          

 29 33  0  0  1  0            999 V2000
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  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
    1.3683   -1.9354    0.0000 O   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
    1.5983   -0.4834    0.0000 O   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
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
  6 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
  5 23  2  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
 24 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.3196    3.2597    1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723    1.9189    1.2048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177    0.9594    0.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    1.2833    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.3340   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5492    0.6358   -0.8080 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6214   -0.2709   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -1.4430   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9304   -2.3151   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -2.0200    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634   -0.8538    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    0.0195    0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    1.2311    1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692    2.2977    0.9229 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3207    3.4961    0.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283    3.1216   -0.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2700    2.2808   -1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463    1.8436   -2.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    2.0378   -0.4923 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5609   -3.0523    0.7347 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364   -3.8449   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -3.5368   -1.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394   -0.9683   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -1.3273    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460   -2.6396    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0707   -3.6453   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3280   -0.3524    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727   -0.7010    1.1134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7366   -0.7260    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0301    3.9308    1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451    3.3376    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1115    3.5908    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    2.3264    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5109    0.5733   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -1.7236   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -0.6458    2.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    0.9015    2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    1.5824    1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    2.6009    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6456    4.3651    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    3.6517    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    2.8053   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145   -4.8997   -0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973   -3.5753   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -1.7948   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847   -4.6568   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -3.5085   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832   -3.6225    0.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6048   -0.7621    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8539    0.1565   -0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7832   -1.6558   -0.3049 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  6
 19 42  1  6
 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


  Mrv1652309022200312D          

 29 33  0  0  1  0            999 V2000
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  1  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
    1.3683   -1.9354    0.0000 O   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
    1.5983   -0.4834    0.0000 O   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
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
  6 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
  5 23  2  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
 24 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)[C@H]1C2[C@H](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/t13-,19+,20?/m0/s1

> <INCHI_KEY>
ZGLXUQQMLLIKAN-XIXJEIPKSA-N

> <FORMULA>
C22H22O7

> <MOLECULAR_WEIGHT>
398.411

> <EXACT_MASS>
398.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.856564129467564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
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>
72.45000000000002

> <JCHEM_REFRACTIVITY>
102.48830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.925   2.547   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   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       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.590   4.087   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.924   4.857   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14    6                                                  
CONECT   20   10   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    9                                                       
CONECT   23    5   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₇

Average Mass

398.4110 Da

Monoisotopic Mass

398.13655 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1C2[C@H](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/t13-,19+,20?/m0/s1

InChI Key

ZGLXUQQMLLIKAN-XIXJEIPKSA-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

Not Available

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
Oxolane
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

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	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	40.86 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

74162806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71045228

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Antunez-Mojica M, Rojas-Sepulveda AM, Mendieta-Serrano MA, Gonzalez-Maya L, Marquina S, Salas-Vidal E, Alvarez L: Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos. Molecules. 2018 Dec 20;24(1). pii: molecules24010008. doi: 10.3390/molecules24010008. [PubMed:30577489 ]
Liu Y, Young K, Rakotondraibe LH, Brodie PJ, Wiley JD, Cassera MB, Callmander MW, Rakotondrajaona R, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Kingston DG: Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest. J Nat Prod. 2015 Jul 24;78(7):1543-7. doi: 10.1021/np501020m. Epub 2015 Jun 19. [PubMed:26091020 ]
Moise IM, Bicu E, Farce A, Dubois J, Ghinet A: Indolizine-phenothiazine hybrids as the first dual inhibitors of tubulin polymerization and farnesyltransferase with synergistic antitumor activity. Bioorg Chem. 2020 Oct;103:104184. doi: 10.1016/j.bioorg.2020.104184. Epub 2020 Aug 26. [PubMed:32891861 ]
Maleck M, Hollanda PO, Serdeiro MT, Soares RO, Honorio NA, Silva CG: Toxicity and Larvicidal Activity of Podophyllum-Based Lignans Against Aedes aegypti (Diptera: Culicidae). J Med Entomol. 2017 Jan;54(1):159-166. doi: 10.1093/jme/tjw130. Epub 2016 Aug 25. [PubMed:28082643 ]
Wu Z, Zhao Y, Zhang Y, Zhu L: HY-2, a novel DNA topoisomerase II inhibitor, induces G2/M cell cycle arrest in HCT-116 cells. J Chemother. 2014 Dec;26(6):342-7. doi: 10.1179/1973947813Y.0000000153. Epub 2013 Dec 6. [PubMed:24188177 ]
LOTUS database [Link]

Showing NP-Card for (10r,15r)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0143692)

MOL for NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-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 NP0143692 ((10r,15r)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)