NP-MRD: Showing NP-Card for 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol (NP0289649)

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Record Information

Version

2.0

Created at

2022-09-09 19:56:26 UTC

Updated at

2022-09-09 19:56:26 UTC

NP-MRD ID

NP0289649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol

Description

16,17-Dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol is found in Argemone mexicana, Berberis insignis, Berberis umbellata, Berberis vulgaris, Coptis japonica, Hydrastis canadensis and Toddalia asiatica. 16,17-Dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081702362D          

 26 30  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  2  0  0  0  0
 19 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21  6  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23 15  1  0  0  0  0
 24  2  1  0  0  0  0
 24 19  1  0  0  0  0
 25 10  1  0  0  0  0
 25 16  1  0  0  0  0
 26 10  1  0  0  0  0
 26 17  1  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
   -6.0712    2.1549    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731    0.9450   -0.1172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787    0.9944   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868    2.1659    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    2.2478    0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647    1.1153   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148   -0.0711   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2097   -0.1387   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622   -1.3333   -0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2684   -2.2272    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0220   -1.2674   -0.6549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6155   -2.4603   -0.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -1.1856   -0.2890 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -2.4278   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313   -2.3577   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.0886   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.9877   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571    0.1958    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173    1.3444    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    1.2648    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    0.0691   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.0647   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068    1.1840   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005    2.3712    0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7180    1.8947    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129    0.5486    0.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8218    2.6011    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1535    2.0566   -0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289    2.9303   -0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8981    3.0577    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233    3.1906    0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7359   -2.0994    1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -3.2892    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3670   -2.0877    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.3201   -1.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200   -3.1788   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -3.2525   -0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988   -2.6437    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -2.6305   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953   -3.1395    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650   -1.8913   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706    2.1669    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264    2.1422    0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9175    1.9133    1.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    2.4592    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 23  1  0
 23 22  2  0
 22 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 19 20  1  0
 20 21  2  0
 13 11  1  0
 11 12  1  0
  4  3  1  0
 21 22  1  0
 11  7  1  0
 21 16  1  0
 26 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
  5 31  1  0
  4 30  1  0
 23 43  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 25 44  1  0
 25 45  1  0
 20 42  1  0
 11 35  1  6
 12 36  1  0
M  END


  Mrv1652310081702362D          

 26 30  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319    1.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  2  0  0  0  0
 19 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 18  1  0  0  0  0
 21  6  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23 15  1  0  0  0  0
 24  2  1  0  0  0  0
 24 19  1  0  0  0  0
 25 10  1  0  0  0  0
 25 16  1  0  0  0  0
 26 10  1  0  0  0  0
 26 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C=C1)C=C1N(CCC3=CC4=C(OCO4)C=C13)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9,20,22H,5-6,10H2,1-2H3

> <INCHI_KEY>
ZRBGFWOXAQPDTH-UHFFFAOYSA-N

> <FORMULA>
C20H19NO5

> <MOLECULAR_WEIGHT>
353.374

> <EXACT_MASS>
353.126322716

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.77966992039305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.4727701746666666

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.451034087147278

> <JCHEM_PKA_STRONGEST_BASIC>
-0.05212277677647725

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
96.71929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         0                                  
HETATM    1  C   UNK     0       4.173  -0.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.293   2.472   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.752  -2.885   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.212  -2.862   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.912   2.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.542  -1.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.462  -1.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.582   1.104   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       8.833   2.449   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.922  -1.493   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3    4   12                                                       
CONECT    4    3   15                                                       
CONECT    5    6   11                                                       
CONECT    6    5   21                                                       
CONECT    7   12   14                                                       
CONECT    8   11   16                                                       
CONECT    9   13   17                                                       
CONECT   10   25   26                                                       
CONECT   11    5    8   13                                                  
CONECT   12    3    7   18                                                  
CONECT   13    9   11   14                                                  
CONECT   14    7   13   21                                                  
CONECT   15    4   19   23                                                  
CONECT   16    8   17   25                                                  
CONECT   17    9   16   26                                                  
CONECT   18   12   19   20                                                  
CONECT   19   15   18   24                                                  
CONECT   20   18   21   22                                                  
CONECT   21    6   14   20                                                  
CONECT   22   20                                                            
CONECT   23    1   15                                                       
CONECT   24    2   19                                                       
CONECT   25   10   16                                                       
CONECT   26   10   17                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₉NO₅

Average Mass

353.3740 Da

Monoisotopic Mass

353.12632 Da

IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol

Traditional Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-ol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)C=C1N(CCC3=CC4=C(OCO4)C=C13)C2O

InChI Identifier

InChI=1S/C20H19NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9,20,22H,5-6,10H2,1-2H3

InChI Key

ZRBGFWOXAQPDTH-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
Argemone mexicana	LOTUS Database	35616633
Berberis insignis	LOTUS Database	35616633
Berberis umbellata	LOTUS Database	35616633
Berberis vulgaris	LOTUS Database	35616633
Coptis japonica	LOTUS Database	35616633
Hydrastis canadensis	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Acetal
Alkanolamine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen 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	2.36	ALOGPS
logP	2.47	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	-0.052	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.72 m³·mol⁻¹	ChemAxon
Polarizability	37.78 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

HMDB0162670

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24974

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol (NP0289649)

MOL for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

3D MOL for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

3D SDF for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

3D-SDF for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

PDB for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

3D PDB for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

SMILES for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

INCHI for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

Structure for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)

3D Structure for NP0289649 (16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-ol)