NP-MRD: Showing NP-Card for 8-Oxoberberine (NP0068129)

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Record Information

Version

2.0

Created at

2022-04-28 13:07:50 UTC

Updated at

2026-02-19 00:00:50 UTC

NP-MRD ID

NP0068129

Natural Product DOI

https://doi.org/10.57994/7630

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Oxoberberine

Description

Berlambine, also known as JKL-1073a or 8-oxoberberine, belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety. 8-Oxoberberine is found in Acangelisia gusanlung, Arcangelisia gusanlung, Berberies amurensis, Berberis actinacantha, Berberis aquifolium, Berberis buxifolia, Berberis cretica, Berberis empetrifolia, Berberis empetrifolia Lam. , Berberis japonica, Berberis lambertii, Berberis lycium Royle , Berberis turcomanica, Berberis vulgaris , Coptis japonica, Coptis spp., Coscinium fenestratum (Gaertn.) Colebr. , Glaucium arabicum, Phellodendron amurense , Thalictrum acutifolium, Thalictrum alpinum L., Thalictrum foliolosum, Thalictrum foliolosum DC , Thalictrum javanicum, Thalictrum longistylum DC, Thalictrum minus Race B and Thalictrum podocarpum Humb.. Berlambine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517172D          

 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
    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
    5.9366   -0.8501    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
    5.9584    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
    9.6389   -0.3634    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
    8.9540   -1.5092    0.0000 O   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
    5.1335    0.5912    0.0000 C   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
    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
  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -6.2393    0.8882    1.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731    0.1552    0.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099    0.3712    0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    1.2631    1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044    1.4386    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.7131    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.8436    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829    0.0901   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -0.7794   -1.1181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138   -0.9275   -1.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -1.7514   -2.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778   -0.1837   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -0.3400   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6957   -1.2380   -1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9343   -2.5877   -0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1731   -1.6248   -1.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -1.0833   -2.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -0.2907   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954   -0.0969   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0926    0.7088   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945    1.3601    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075    1.1841    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3351    0.3642   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1790    2.0759    1.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4845    1.4871    1.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4433    1.0324    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063    1.9437    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2382    0.3960    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8891    0.8667    2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    1.8338    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599    2.1193    2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5185    1.5399    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8000   -3.1842   -1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2490   -2.9032   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804   -2.7269   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288   -2.6067   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.8931   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182   -0.4238   -3.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2225   -1.9125   -2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0779   -0.6352   -1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3680    1.7171    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2757    2.2161    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566    0.5811    2.0833 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  7  1  0
  7  8  2  0
  8  9  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 21 22  1  0
 22 23  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13  3  1  0
 12  6  1  0
 23  8  1  0
 23 18  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 25 42  1  0
 25 43  1  0
 22 41  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END


  Mrv1533004171517172D          

 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
    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
    5.9366   -0.8501    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
    5.9584    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
    9.6389   -0.3634    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
    8.9540   -1.5092    0.0000 O   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
    5.1335    0.5912    0.0000 C   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
    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
  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)C(=O)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H17NO5/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/h3-4,7-9H,5-6,10H2,1-2H3

> <INCHI_KEY>
ZHYQCBCBTQWPLC-UHFFFAOYSA-N

> <FORMULA>
C20H17NO5

> <MOLECULAR_WEIGHT>
351.358

> <EXACT_MASS>
351.110672651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.31414560650254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.193589775

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.344802216057309

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
96.01849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.173  -0.148   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      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.912   2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.582   1.104   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.833   2.449   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.963   1.174   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    8   12                                                  
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
JKL-1073a	MeSH
JKL 1073a	MeSH
8-Oxoberberine	MeSH

Chemical Formula

C₂₀H₁₇NO₅

Average Mass

351.3580 Da

Monoisotopic Mass

351.11067 Da

IUPAC 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-one

Traditional 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-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)C(=O)C2=C1OC

InChI Identifier

InChI=1S/C20H17NO5/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/h3-4,7-9H,5-6,10H2,1-2H3

InChI Key

ZHYQCBCBTQWPLC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acangelisia gusanlung	Plant	KNApSAcK
Arcangelisia gusanlung	LOTUS Database	35616633
Berberies amurensis	-	KNApSAcK
Berberis actinacantha	LOTUS Database	35616633
Berberis aquifolium	LOTUS Database	35616633
Berberis buxifolia	LOTUS Database	35616633
Berberis cretica	LOTUS Database	35616633
Berberis empetrifolia	LOTUS Database	35616633
Berberis empetrifolia Lam.	Plant	KNApSAcK
Berberis japonica	LOTUS Database	35616633
Berberis lambertii	Plant	KNApSAcK
Berberis lycium	Plant	KNApSAcK
Berberis turcomanica	Plant	KNApSAcK
Berberis vulgaris	Plant	KNApSAcK
Coptis japonica	LOTUS Database	35616633
Coptis spp.	Plant	KNApSAcK
Coscinium fenestratum	Plant	KNApSAcK
Glaucium arabicum	Plant	KNApSAcK
Phellodendron amurense	Plant	KNApSAcK
Thalictrum acutifolium	Plant	KNApSAcK
Thalictrum alpinum	Plant	KNApSAcK
Thalictrum foliolosum	LOTUS Database	35616633
Thalictrum foliolosum DC	Plant	KNApSAcK
Thalictrum javanicum Blume	LOTUS Database	35616633
Thalictrum longistylum DC	Plant	KNApSAcK
Thalictrum minus Race B	Plant	KNApSAcK
Thalictrum podocarpum Humb.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinolones and derivatives

Direct Parent

Isoquinolones and derivatives

Alternative Parents

Substituents

Isoquinolone
Benzodioxole
Anisole
Alkyl aryl ether
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactam
Oxacycle
Acetal
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	2.63	ALOGPS
logP	2.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.02 m³·mol⁻¹	ChemAxon
Polarizability	37.31 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

11066

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1016/j.molstruc.2003.09.018

Showing NP-Card for 8-Oxoberberine (NP0068129)

MOL for NP0068129 (8-Oxoberberine)

3D MOL for NP0068129 (8-Oxoberberine)

3D SDF for NP0068129 (8-Oxoberberine)

3D-SDF for NP0068129 (8-Oxoberberine)

PDB for NP0068129 (8-Oxoberberine)

3D PDB for NP0068129 (8-Oxoberberine)

SMILES for NP0068129 (8-Oxoberberine)

INCHI for NP0068129 (8-Oxoberberine)

Structure for NP0068129 (8-Oxoberberine)

3D Structure for NP0068129 (8-Oxoberberine)