NP-MRD: Showing NP-Card for 16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one (NP0263679)

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Record Information

Version

2.0

Created at

2022-09-08 06:56:22 UTC

Updated at

2022-09-08 06:56:22 UTC

NP-MRD ID

NP0263679

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one

Description

5-Methoxydehydropodophyllotoxin, also known as 5-MDH-podophyllotoxin, belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. 16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one is found in Condea verticillata. 16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one was first documented in 1993 (PMID: 8277312). Based on a literature review very few articles have been published on 5-Methoxydehydropodophyllotoxin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082208562D          

 32 36  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
    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
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    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
    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
    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
    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
  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  1  0  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    3.8720   -1.7635    2.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1694   -1.3680    1.5926 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3065   -0.7358    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -0.4403    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022    0.1924    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835    0.4494    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220    1.3673    1.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9074    1.6129    2.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307    0.8846    1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252    1.1008    1.8597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350   -0.0408    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943   -0.7972   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9284   -0.5894    0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674    0.3732   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3122   -1.7438   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.9359   -1.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049   -1.1921   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -0.2649    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -2.9194   -2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -3.2092   -2.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237   -2.5944   -1.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070    2.6599    3.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    2.9446    3.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    2.2303    2.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193    2.2530    2.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    0.5344   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430    0.2495   -1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.5821   -2.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4126    1.2271   -3.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436   -0.3925   -0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0396   -0.6592   -0.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124    0.3557   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147   -2.3437    2.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232   -2.3521    3.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -0.8620    3.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6637   -0.7082    2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    1.7535    2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055    1.0173    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3595   -0.1523   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0103    1.0155   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207   -1.3510   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -2.8518   -3.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5266   -4.3093   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    3.5507    2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2832    2.2206    4.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713    1.0350   -1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    2.2573   -3.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8160    1.1826   -4.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913    0.5724   -3.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5569    1.3509   -0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6864    0.4547   -1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6452    0.1491    0.0994 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 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 30 31  1  0
 31 32  1  0
  5  6  1  0
  6 18  1  0
 18 17  2  0
 17 16  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 15  1  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  1  0
 30  3  1  0
  7  6  2  0
 11 18  1  0
 22  8  1  0
 15 16  2  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
 26 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
 32 50  1  0
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 32 52  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 10 37  1  0
 22 44  1  0
 22 45  1  0
M  END


  Mrv1652309082208562D          

 32 36  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
    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
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   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
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    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
    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
    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
    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
  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  1  0  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263679

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1=C2C=C3OCOC3=C(OC)C2=C(O)C2=C1C(=O)OC2

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O9/c1-26-13-5-10(6-14(27-2)20(13)28-3)16-11-7-15-21(32-9-31-15)22(29-4)18(11)19(24)12-8-30-23(25)17(12)16/h5-7,24H,8-9H2,1-4H3

> <INCHI_KEY>
OJSCBCNNQXLIJG-UHFFFAOYSA-N

> <FORMULA>
C23H20O9

> <MOLECULAR_WEIGHT>
440.404

> <EXACT_MASS>
440.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.2625811663215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <JCHEM_LOGP>
2.8536352833333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.709001897063118

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.635501966522543

> <JCHEM_PKA_STRONGEST_BASIC>
-4.198463915419191

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
111.82489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         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       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.259   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   11                                                  
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15                                                       
CONECT   22    8   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7   25                                                  
CONECT   25   24                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    3   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-MDH-Podophyllotoxin	MeSH

Chemical Formula

C₂₃H₂₀O₉

Average Mass

440.4040 Da

Monoisotopic Mass

440.11073 Da

IUPAC Name

16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

Traditional Name

16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1=C2C=C3OCOC3=C(OC)C2=C(O)C2=C1C(=O)OC2

InChI Identifier

InChI=1S/C23H20O9/c1-26-13-5-10(6-14(27-2)20(13)28-3)16-11-7-15-21(32-9-31-15)22(29-4)18(11)19(24)12-8-30-23(25)17(12)16/h5-7,24H,8-9H2,1-4H3

InChI Key

OJSCBCNNQXLIJG-UHFFFAOYSA-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
Condea verticillata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Lignan lactone
Arylnaphthalene lignan skeleton
Linear furanonaphthodioxole
Naphthofuran
1-naphthol
Naphthalene
Phthalide
Isobenzofuranone
Benzodioxole
Isocoumaran
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	2.85	ChemAxon
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.82 m³·mol⁻¹	ChemAxon
Polarizability	44.26 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

118154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Novelo M, Cruz JG, Hernandez L, Pereda-Miranda R, Chai H, Mar W, Pezzuto JM: Cytotoxic constituents from Hyptis verticillata. J Nat Prod. 1993 Oct;56(10):1728-36. doi: 10.1021/np50100a011. [PubMed:8277312 ]
LOTUS database [Link]

Showing NP-Card for 16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one (NP0263679)

MOL for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D MOL for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D SDF for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D-SDF for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

PDB for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D PDB for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

SMILES for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

INCHI for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

Structure for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D Structure for NP0263679 (16-hydroxy-2-methoxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)