NP-MRD: Showing NP-Card for methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate (NP0196876)

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Record Information

Version

2.0

Created at

2022-09-04 15:01:56 UTC

Updated at

2022-09-04 15:01:56 UTC

NP-MRD ID

NP0196876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate

Description

Steganoate B, also known as steganoic acid b, belongs to the class of organic compounds known as dibenzocyclooctadiene lignans. Dibenzocyclooctadiene lignans are compounds containing a dibenzocyclooctadiene moiety, which consists of two hydroxylated benzene connected by a cycloheptene ring. methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate is found in Steganotaenia araliacea. methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate was first documented in 1993 (PMID: 8133298). Based on a literature review very few articles have been published on steganoate B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217012D          

 31 34  0  0  1  0            999 V2000
    8.1977    6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6926    5.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751    5.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5627    6.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7794    4.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5624    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9913    3.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7040    2.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2714    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5551    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5515    0.8786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642    0.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262    1.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0502    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4002    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578    4.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741    5.0828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4700    5.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    6.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2548    1.8415    0.0000 O   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
  5  3  1  6  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
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    5.4368   -2.2178    1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2464   -1.4556    1.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862   -1.5822    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -2.3916   -0.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201   -0.8043    0.4214 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2321   -1.2945   -0.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2212   -1.1486   -0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8336   -2.3600   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970   -3.4794   -1.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985   -4.7429   -1.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -2.4627   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9614   -1.3526   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179   -1.5504    0.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9714   -2.7674   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -0.1311    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    0.9883    0.4267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146    1.3296    1.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.0521   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005    1.3567    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7539    2.0034   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828    3.3656   -0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    4.0795    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2927    3.3827    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3406    2.0156    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.5284    1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    0.6394    0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7200    0.8389    0.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    1.4084   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    5.4223    0.0714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518    5.5926   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6942    4.2844   -0.9884 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2133   -1.7628    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8540   -2.2075    2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2705   -3.2498    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136   -1.0901    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -2.3980   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -0.8390   -1.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757   -4.7080   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0505   -5.5400   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790   -5.0081   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555   -3.4348   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2084   -3.0059   -1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4648   -3.6200    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9687   -2.6800    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    0.9325    2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312    2.4383    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2469    1.0292    2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4503    1.4372   -1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002    3.8903    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    2.4315    1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3442    1.0016    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    1.0032   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503    2.3818   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823    0.7541   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653    1.5495   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997    6.1221   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    6.1296   -0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 31  1  0
 31 30  1  0
 30 29  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  5 26  1  0
 19 24  1  0
  7 18  1  0
 29 22  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 26 52  1  6
 25 50  1  0
 25 51  1  0
 23 49  1  0
 30 56  1  0
 30 57  1  0
 20 48  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 11 41  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  6 36  1  0
  6 37  1  0
  5 35  1  1
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652309042217012D          

 31 34  0  0  1  0            999 V2000
    8.1977    6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6926    5.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751    5.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5627    6.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7794    4.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5624    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9913    3.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7040    2.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2714    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5551    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5515    0.8786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642    0.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262    1.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0502    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8095    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4002    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578    4.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741    5.0828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4700    5.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    6.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2548    1.8415    0.0000 O   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
  5  3  1  6  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
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CC2=CC3=C(OCO3)C=C2C2=C(OC)C(OC)=CC(OC)=C2C[C@H]1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O8/c1-25-16-6-12-7-18-19(31-11-30-18)9-13(12)21-14(8-15(16)23(24)29-5)17(26-2)10-20(27-3)22(21)28-4/h7,9-10,15-16H,6,8,11H2,1-5H3/t15-,16-/m1/s1

> <INCHI_KEY>
PSZQHRCYUYZKHC-HZPDHXFCSA-N

> <FORMULA>
C23H26O8

> <MOLECULAR_WEIGHT>
430.453

> <EXACT_MASS>
430.162767797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.85062426868359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (9R,10R)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate

> <JCHEM_LOGP>
3.003899060666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8807828591359965

> <JCHEM_POLAR_SURFACE_AREA>
81.68000000000002

> <JCHEM_REFRACTIVITY>
111.1086

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (9R,10R)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      15.302  11.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.359  10.093   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.834  10.300   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.250  11.726   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.891   9.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.655   7.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.250   6.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.580   5.484   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.917   6.248   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.247   5.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.573   3.944   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.236   3.180   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.230   1.640   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.560   0.864   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.906   3.956   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.569   3.192   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.562   1.652   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.913   5.496   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.427   5.901   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.651   4.571   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.111   4.577   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.347   5.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.123   7.245   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.663   7.238   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.068   8.724   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.405   9.488   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.211  11.016   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.436  11.948   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.839   5.601   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.672   4.070   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.076   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    7   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   22   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   21                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Steganoic acid b	Generator

Chemical Formula

C₂₃H₂₆O₈

Average Mass

430.4530 Da

Monoisotopic Mass

430.16277 Da

IUPAC Name

methyl (9R,10R)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate

Traditional Name

methyl (9R,10R)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CC2=CC3=C(OCO3)C=C2C2=C(OC)C(OC)=CC(OC)=C2C[C@H]1C(=O)OC

InChI Identifier

InChI=1S/C23H26O8/c1-25-16-6-12-7-18-19(31-11-30-18)9-13(12)21-14(8-15(16)23(24)29-5)17(26-2)10-20(27-3)22(21)28-4/h7,9-10,15-16H,6,8,11H2,1-5H3/t15-,16-/m1/s1

InChI Key

PSZQHRCYUYZKHC-HZPDHXFCSA-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
Steganotaenia araliacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocyclooctadiene lignans. Dibenzocyclooctadiene lignans are compounds containing a dibenzocyclooctadiene moiety, which consists of two hydroxylated benzene connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzocyclooctadiene lignans

Sub Class

Not Available

Direct Parent

Dibenzocyclooctadiene lignans

Alternative Parents

Substituents

Dibenzocyclooctane lignan
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Methyl ester
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen 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	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.11 m³·mol⁻¹	ChemAxon
Polarizability	44.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23327306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wickramaratne DB, Pengsuparp T, Mar W, Chai HB, Chagwedera TE, Beecher CW, Farnsworth NR, Kinghorn AD, Pezzuto JM, Cordell GA: Novel antimitotic dibenzocyclo-octadiene lignan constituents of the stem bark of Steganotaenia araliacea. J Nat Prod. 1993 Dec;56(12):2083-90. doi: 10.1021/np50102a009. [PubMed:8133298 ]
LOTUS database [Link]

Showing NP-Card for methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate (NP0196876)

MOL for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

3D MOL for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

3D SDF for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

3D-SDF for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

PDB for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

3D PDB for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

SMILES for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

INCHI for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

Structure for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)

3D Structure for NP0196876 (methyl (9r,10r)-3,4,6,10-tetramethoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaene-9-carboxylate)