NP-MRD: Showing NP-Card for (14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene (NP0213908)

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Record Information

Version

2.0

Created at

2022-09-05 13:03:07 UTC

Updated at

2022-09-05 13:03:07 UTC

NP-MRD ID

NP0213908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

ZINC2030457 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. (14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene is found in Berberis integerrima and Berberis lycium. Based on a literature review very few articles have been published on ZINC2030457.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215032D          

 29 33  0  0  1  0            999 V2000
    2.2137   -1.5080    0.0000 C   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
    3.4619   -0.8125    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
    4.6884   -1.5457    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
    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
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7319    1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    2.0326    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4525    1.7135    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.9103    0.0000 Cl  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
    6.3817    1.2868    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
    7.6082    0.5536    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
    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
    7.5864   -0.8752    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
    5.9366   -0.8501    0.0000 C   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
    9.7127   -1.1851    0.0000 C   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
  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
  6 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -5.9553    2.0612    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2006    0.8822    0.8481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8491    0.9311    0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505    2.1125    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    2.2098   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    1.0197   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7222   -0.1913    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0794   -0.2515    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367   -1.3628    0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977   -2.3391    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242   -1.4092   -0.0113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8976   -1.8024   -1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0325   -3.3048   -1.7146 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5631   -2.4430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -1.9760   -2.1770 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -1.1630    0.4229 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -2.0582    1.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -2.1776    0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.8721    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578   -0.7922    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273    0.4044   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604    1.5057   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698    1.4353   -0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.2165   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246    0.1010    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    1.1523   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736    2.5865   -0.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047    2.2102   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5487    0.8036   -0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4784    2.8823    1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9285    1.8677    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2030    2.4251   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223    3.0433    0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213    3.1303   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8705   -3.2529    0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0096   -2.0909   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -2.7490    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -2.2192    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -3.1048    1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3391   -1.7056    2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158   -2.7795   -0.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -2.7548    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153   -1.6854    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    2.3302   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7023    2.1394   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2790    2.4308   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9895    2.7246    0.5201 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  6  2  0
  6 26  1  0
 26 25  2  0
 25 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 22 23  1  0
 23 24  2  0
 16 11  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  8  3  1  0
  7  6  1  0
 24 25  1  0
 24 19  1  0
 29 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
 26 45  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 28 46  1  0
 28 47  1  0
 23 44  1  0
 11 38  1  1
 10 35  1  0
 10 36  1  0
 10 37  1  0
M  END


  Mrv1652309052215032D          

 29 33  0  0  1  0            999 V2000
    2.2137   -1.5080    0.0000 C   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
    3.4619   -0.8125    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
    4.6884   -1.5457    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
    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
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7319    1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    2.0326    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4525    1.7135    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.9103    0.0000 Cl  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
    6.3817    1.2868    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
    7.6082    0.5536    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
    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
    7.5864   -0.8752    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
    5.9366   -0.8501    0.0000 C   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
    9.7127   -1.1851    0.0000 C   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
  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
  6 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)[C@@H](C2=C1OC)C(Cl)(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C21H18Cl3NO4/c1-26-15-4-3-12-7-14-13-9-17-16(28-10-29-17)8-11(13)5-6-25(14)20(21(22,23)24)18(12)19(15)27-2/h3-4,7-9,20H,5-6,10H2,1-2H3/t20-/m0/s1

> <INCHI_KEY>
CAGHPRDTHLKFCW-FQEVSTJZSA-N

> <FORMULA>
C21H18Cl3NO4

> <MOLECULAR_WEIGHT>
454.73

> <EXACT_MASS>
453.0301412

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
44.48409884478176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14S)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15,17,19-heptaene

> <JCHEM_LOGP>
4.471917210333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.043776197673490835

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
115.31409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(14S)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15,17,19-heptaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.132  -2.815   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.922  -1.493   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.462  -1.517   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       8.752  -2.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542  -1.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.963   1.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.582   1.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.833   2.449   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       8.083   3.794   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0      10.178   3.198   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0       7.488   1.699   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      11.912   2.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   16                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   16   26                                                  
CONECT   26   25    6                                                       
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈Cl₃NO₄

Average Mass

454.7300 Da

Monoisotopic Mass

453.03014 Da

IUPAC Name

(14S)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15,17,19-heptaene

Traditional Name

(14S)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,15,17,19-heptaene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)[C@@H](C2=C1OC)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C21H18Cl3NO4/c1-26-15-4-3-12-7-14-13-9-17-16(28-10-29-17)8-11(13)5-6-25(14)20(21(22,23)24)18(12)19(15)27-2/h3-4,7-9,20H,5-6,10H2,1-2H3/t20-/m0/s1

InChI Key

CAGHPRDTHLKFCW-FQEVSTJZSA-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
Berberis integerrima	LOTUS Database	35616633
Berberis lycium	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
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Enamine
Ether
Organic nitrogen compound
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Alkyl halide
Alkyl chloride
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	4.47	ChemAxon
pKa (Strongest Basic)	-0.044	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.31 m³·mol⁻¹	ChemAxon
Polarizability	44.48 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

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

92170520

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene (NP0213908)

MOL for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

3D MOL for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

3D SDF for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

3D-SDF for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

PDB for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

3D PDB for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

SMILES for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

INCHI for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

Structure for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)

3D Structure for NP0213908 ((14s)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene)