NP-MRD: Showing NP-Card for (3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol (NP0321165)

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Record Information

Version

2.0

Created at

2022-09-11 23:14:05 UTC

Updated at

2022-09-11 23:14:05 UTC

NP-MRD ID

NP0321165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol

Description

Decursivine belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol is found in Rhaphidophora decursiva. (3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol was first documented in 2017 (PMID: 28385033). Based on a literature review a small amount of articles have been published on Decursivine (PMID: 30488047) (PMID: 35412317) (PMID: 34620892) (PMID: 34376138).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122201142D          

 26 31  0  0  1  0            999 V2000
    4.2244   -2.5076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -2.7752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538   -2.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705   -2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705   -1.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -1.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -0.2406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538    0.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    0.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -1.3669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1846   -1.0610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8952   -1.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6134   -1.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -2.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5983   -2.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8876   -2.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -3.5326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820   -3.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9245   -2.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -0.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
 15 13  1  6  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  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
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 12 26  1  0  0  0  0
M  END

     RDKit          3D

 42 47  0  0  0  0  0  0  0  0999 V2000
    0.2054   -2.4811   -0.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4230   -1.5323    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556   -2.0392    1.3662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9644   -1.3456    2.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3651   -1.2442    1.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318   -0.2974    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8755    0.0754    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9136    0.8977   -0.4023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6817    1.1183   -0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    1.9030   -1.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.9890   -2.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0163    1.2554   -1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447    0.4812   -0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950    0.3642   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -0.1255    0.0107 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7451   -0.0755   -1.1734 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1694    0.0267   -0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.6008   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    0.7443   -1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388    0.3050   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785   -0.2658    0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7079   -0.4097    0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8432   -0.6259    1.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0756    0.1092    1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.3053    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3673    1.1701   -1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325   -2.7958   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188   -2.0352    3.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4663   -0.4023    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6754   -2.2928    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0809   -0.9833    2.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6689   -0.3064    1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7850    1.3388   -0.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    2.4681   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118    2.6030   -3.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    0.4114    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -0.9010   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6717    0.9649   -2.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723    1.1925   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565   -0.8548    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9093   -0.4249    2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855    1.1143    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 26  1  0
 26 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 15  2  1  0
 22 17  1  0
 14  6  1  0
 21 20  1  0
 14  9  1  0
 13 12  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 16 37  1  6
 15 36  1  1
 18 38  1  0
 19 39  1  0
 24 41  1  0
 24 42  1  0
 22 40  1  0
M  END


  Mrv1652309122201142D          

 26 31  0  0  1  0            999 V2000
    4.2244   -2.5076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -2.7752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538   -2.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705   -2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705   -1.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -1.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -0.2406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538    0.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    0.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0538   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4622   -1.3669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1846   -1.0610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8952   -1.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6134   -1.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3165   -2.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5983   -2.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8876   -2.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -3.5326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5820   -3.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9245   -2.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -0.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
 15 13  1  6  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  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
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 12 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NCCC2=CNC3=CC=C4O[C@H]([C@H]1C4=C23)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16N2O4/c23-20-18-17-14(4-2-12-16(17)11(8-22-12)5-6-21-20)26-19(18)10-1-3-13-15(7-10)25-9-24-13/h1-4,7-8,18-19,22H,5-6,9H2,(H,21,23)/t18-,19+/m1/s1

> <INCHI_KEY>
WBLUYASSOGHQQA-MOPGFXCFSA-N

> <FORMULA>
C20H16N2O4

> <MOLECULAR_WEIGHT>
348.358

> <EXACT_MASS>
348.111007003

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.79375864067693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3-(2H-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0^{4,15}.0^{12,16}]hexadeca-1(14),5,9,12,15-pentaen-5-ol

> <JCHEM_LOGP>
1.7907825282583627

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.404716185076722

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.753994513352632

> <JCHEM_PKA_STRONGEST_BASIC>
5.419315713770795

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
93.60310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-3-(2H-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0^{4,15}.0^{12,16}]hexadeca-1(14),5,9,12,15-pentaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       7.886  -4.681   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.463  -4.091   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.374  -5.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.834  -5.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.745  -4.091   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.745  -2.551   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.397  -1.981   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.558  -0.449   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.064  -0.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.834   1.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.374   1.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.144  -0.129   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.374  -1.463   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.834  -1.463   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.463  -2.551   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.811  -1.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.138  -2.763   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.478  -2.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.805  -2.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.791  -4.327   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.450  -5.085   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.124  -4.303   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.756  -6.594   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.286  -6.769   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.926  -5.368   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.650  -0.449   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    6    9                                                  
CONECT   15   13    2   16                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆N₂O₄

Average Mass

348.3580 Da

Monoisotopic Mass

348.11101 Da

IUPAC Name

(3R,4R)-3-(2H-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0^{4,15}.0^{12,16}]hexadeca-1(14),5,9,12,15-pentaen-5-ol

Traditional Name

(3R,4R)-3-(2H-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0^{4,15}.0^{12,16}]hexadeca-1(14),5,9,12,15-pentaen-5-ol

CAS Registry Number

Not Available

SMILES

OC1=NCCC2=CNC3=CC=C4O[C@H]([C@H]1C4=C23)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C20H16N2O4/c23-20-18-17-14(4-2-12-16(17)11(8-22-12)5-6-21-20)26-19(18)10-1-3-13-15(7-10)25-9-24-13/h1-4,7-8,18-19,22H,5-6,9H2,(H,21,23)/t18-,19+/m1/s1

InChI Key

WBLUYASSOGHQQA-MOPGFXCFSA-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
Rhaphidophora decursiva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
3-alkylindole
Benzodioxole
Indole
Indole or derivatives
Coumaran
Alkyl aryl ether
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
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	1.79	ChemAxon
pKa (Strongest Acidic)	2.75	ChemAxon
pKa (Strongest Basic)	5.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	35.79 Å³	ChemAxon
Number of Rings	6	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

77417231

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71560220

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Pitchakuntla M, Jia Y: Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton. Nat Prod Rep. 2019 Apr 17;36(4):666-690. doi: 10.1039/c8np00072g. [PubMed:30488047 ]
Kim DH, Kim HM, Lim JS, Lee HW, Cho CG: Asymmetric Divergent Total Syntheses of (+)-Decursivine and (+)- Serotobenine via Intramolecular Fischer Indole Synthesis. Org Lett. 2022 Apr 22;24(15):2873-2877. doi: 10.1021/acs.orglett.2c00848. Epub 2022 Apr 12. [PubMed:35412317 ]
Parvatkar PT, Smotkin ES, Manetsch R: Total synthesis of (+/-)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization. Sci Rep. 2021 Oct 7;11(1):19915. doi: 10.1038/s41598-021-99064-8. [PubMed:34620892 ]
Hasan A, Jannat K, Bondhon TA, Jahan R, Hossan MS, de Lourdes Pereira M, Nissapatorn V, Wiart C, Rahmatullah M: Can Antimalarial Phytochemicals be a Possible Cure for COVID-19? Molecular Docking Studies of Some Phytochemicals to SARS-CoV-2 3C-like Protease. Infect Disord Drug Targets. 2022;22(1):e290721195143. doi: 10.2174/1871526521666210729164054. [PubMed:34376138 ]
Mbabi Nyemeck N 2nd, Serge Ngono Bikobo D, Abouem A Zintchem A, Schafer EM, Bochet C, Emmanuel Pegnyemb D, Koert U: A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (+/-)-serotobenine. Nat Prod Res. 2017 Dec;31(24):2875-2884. doi: 10.1080/14786419.2017.1305378. Epub 2017 Apr 7. [PubMed:28385033 ]
LOTUS database [Link]

Showing NP-Card for (3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol (NP0321165)

MOL for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

3D MOL for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

3D SDF for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

3D-SDF for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

PDB for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

3D PDB for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

SMILES for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

INCHI for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

Structure for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)

3D Structure for NP0321165 ((3r,4r)-3-(2h-1,3-benzodioxol-5-yl)-2-oxa-6,11-diazatetracyclo[7.5.2.0⁴,¹⁵.0¹²,¹⁶]hexadeca-1(14),5,9,12,15-pentaen-5-ol)