NP-MRD: Showing NP-Card for Epiberberine (NP0068238)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 13:22:12 UTC

Updated at

2022-04-28 13:22:12 UTC

NP-MRD ID

NP0068238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epiberberine

Description

16,17-Dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14,16,18-octaen-1-ylium 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. Epiberberine is found in Cineraria deltoidea, Cineraria quinquefolia, Copis chinensis, Coptis chinensis , Coptis japonica, Coptis spp., Coptis trifolia, Corydalis yanhusuo, Dioscorea floribunda, Nandina domestica, Sinomenium acutum and Sinomenium acutum Rehder & Wilson . 16,17-Dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14,16,18-octaen-1-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518492D          

 25 29  0  0  0  0            999 V2000
    1.5210   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -3.5164    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  1  0  0  0  0
  6  7  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1   8   1
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -6.0466    1.6681    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295    0.4810    0.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9413    0.4005    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    1.5215    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7476    1.4761    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1773    0.2408    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774   -0.8862   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3621   -0.8395    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -2.0070   -0.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487   -3.2532   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2864    0.1500   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037   -1.0940   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.2240   -0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -2.4524   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696   -2.5173   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314   -1.3805   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050   -0.1616   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.0486   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    1.1603   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0137    1.2618   -0.0137 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4498    2.5683    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9692    2.7159    0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3962    0.7813   -0.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6210    0.1241    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267   -1.1822   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0171    1.5325   -0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3545    1.8578    1.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5711    2.5523   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    2.5104    0.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509   -1.8967   -0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -3.4178    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576   -3.3392   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160   -4.0607   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348   -1.9840   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -3.3587   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325   -3.4939   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    2.0549   -0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    3.1703    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    3.0834   -0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338    2.9915    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396    3.5617   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4926    0.6249   -0.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6504    0.1082    1.3145 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 10  1  0
  6 11  1  0
 11 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 25  1  0
 25 24  1  0
 24 23  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  8  3  1  0
 12 11  1  0
 22  5  1  0
 13 18  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 19 37  1  0
 24 42  1  0
 24 43  1  0
 15 36  1  0
 14 35  1  0
 12 34  1  0
M  CHG  1  20   1
M  END


  Mrv1533004231518492D          

 25 29  0  0  0  0            999 V2000
    1.5210   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9443   -3.5164    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  1  0  0  0  0
  6  7  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0068238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1=[N+](CC2)C=C2C3=C(OCO3)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

> <INCHI_KEY>
FPJQGFLUORYYPE-UHFFFAOYSA-N

> <FORMULA>
C20H18NO4

> <MOLECULAR_WEIGHT>
336.366

> <EXACT_MASS>
336.123034484

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.925209074651704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16,17-dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-1.2833122858050783

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.377300843281597

> <JCHEM_POLAR_SURFACE_AREA>
40.8

> <JCHEM_REFRACTIVITY>
93.5233

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.839  -5.242   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.589  -3.897   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.129  -3.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.878  -2.528   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.418  -2.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.168  -1.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.707  -1.136   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.498  -2.458   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      12.037  -2.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.828  -3.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.368  -3.733   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.380  -2.573   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.797  -3.178   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.659  -4.712   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.158  -5.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.408  -6.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.868  -6.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.078  -5.102   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.538  -5.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -3.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.208  -3.827   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.459  -5.172   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.919  -5.195   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.169  -6.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.629  -6.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    8   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈NO₄

Average Mass

336.3660 Da

Monoisotopic Mass

336.12303 Da

IUPAC Name

16,17-dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

Traditional Name

16,17-dimethoxy-5,7-dioxa-1λ⁵-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1=[N+](CC2)C=C2C3=C(OCO3)C=CC2=C1

InChI Identifier

InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

InChI Key

FPJQGFLUORYYPE-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, 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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cineraria deltoidea	Plant	KNApSAcK
Cineraria quinquefolia	Plant	KNApSAcK
Copis chinensis	-	KNApSAcK
Coptis chinensis	Plant	KNApSAcK
Coptis japonica	LOTUS Database	35616633
Coptis spp.	Plant	KNApSAcK
Coptis trifolia	LOTUS Database	35616633
Corydalis yanhusuo	LOTUS Database	35616633
Dioscorea floribunda	Plant	KNApSAcK
Nandina domestica	LOTUS Database	35616633
Sinomenium acutum	LOTUS Database	35616633
Sinomenium acutum Rehder & Wilson	Plant	KNApSAcK

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
Isoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic cation
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	-0.2	ALOGPS
logP	-1.3	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.52 m³·mol⁻¹	ChemAxon
Polarizability	36.93 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

160876

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epiberberine (NP0068238)

MOL for NP0068238 (Epiberberine)

3D MOL for NP0068238 (Epiberberine)

3D SDF for NP0068238 (Epiberberine)

3D-SDF for NP0068238 (Epiberberine)

PDB for NP0068238 (Epiberberine)

3D PDB for NP0068238 (Epiberberine)

SMILES for NP0068238 (Epiberberine)

INCHI for NP0068238 (Epiberberine)

Structure for NP0068238 (Epiberberine)

3D Structure for NP0068238 (Epiberberine)