NP-MRD: Showing NP-Card for Berberine hydrochloride (NP0138601)

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Record Information

Version

2.0

Created at

2022-06-29 17:37:07 UTC

Updated at

2022-06-29 17:37:07 UTC

NP-MRD ID

NP0138601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Berberine hydrochloride

Description

16,17-Dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride 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-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride is a drug. 16,17-Dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09131211412D          

 26 29  0  0  0  0            999 V2000
   -3.7676    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3443    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -1.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    1.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096   -0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    0.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818    0.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411   -0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316    0.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    0.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447    0.8149    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -3.3661   -0.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194    0.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359   -0.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -1.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 20 17  2  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 19  1  0  0  0  0
M  CHG  2  21   1  26  -1
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -6.2568    1.0894    1.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3203    0.9685    0.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719    0.7426    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922    0.6279    1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1264    0.4002    1.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902    0.2962    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0843    0.0685    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099   -0.0333   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391    0.0794   -1.5386 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8988    0.3009   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    0.4081   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187    0.6349   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661    0.7459   -2.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9724   -0.4627   -2.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2502   -0.0172   -2.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -0.2569   -2.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -0.3769   -1.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355   -0.6059   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016   -0.7186    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.6149    1.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -0.3904    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438   -0.2743   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -0.7752    2.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -0.7175    2.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2902   -0.9420    0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
   -6.3495    0.1402    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2328    1.4436    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8477    1.8938    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.7120    2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    0.3057    2.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089   -0.0137    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3104    0.3968   -2.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756   -1.2659   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9080   -0.2793   -3.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232   -0.8266   -3.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526    0.9462   -3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313   -0.7797   -3.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.2076   -3.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424    0.5204   -2.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1783   -0.6861   -1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.3084    2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231    0.3054    2.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185   -1.4733    2.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  8 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 25  1  0
 25 24  1  0
 24 23  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
  4  3  1  0
 17 22  1  0
  6 11  1  0
 23 20  1  0
 15  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 10 33  1  0
  7 32  1  0
  5 31  1  0
  4 30  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
 18 41  1  0
 16 39  1  0
 16 40  1  0
 15 37  1  0
 15 38  1  0
M  CHG  2   9   1  26  -1
M  END


  Mrv0541 09131211412D          

 26 29  0  0  0  0            999 V2000
   -3.7676    0.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3443    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -1.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    1.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096   -0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    0.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818    0.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411   -0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316    0.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    0.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447    0.8149    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -3.3661   -0.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194    0.8525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359   -0.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -1.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 20 17  2  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 19  1  0  0  0  0
M  CHG  2  21   1  26  -1
M  END
> <DATABASE_ID>
NP0138601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Cl-].COC1=C(OC)C2=C[N+]3=C(C=C2C=C1)C1=CC2=C(OCO2)C=C1CC3

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

> <INCHI_KEY>
VKJGBAJNNALVAV-UHFFFAOYSA-M

> <FORMULA>
C20H18ClNO4

> <MOLECULAR_WEIGHT>
371.814

> <EXACT_MASS>
371.092435776

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.89390818726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16,17-dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-1.2833122858050783

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3828748310453145

> <JCHEM_POLAR_SURFACE_AREA>
40.8

> <JCHEM_REFRACTIVITY>
93.52329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
berberine chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -7.033   0.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.243   1.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.454  -2.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.994  -2.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.247   2.820   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.707   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.124  -1.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.536   1.451   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.956  -1.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.623   1.544   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.925  -1.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.664  -1.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.996   1.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.206   0.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.413   0.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.666   0.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.743  -1.076   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.286   0.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.495  -1.216   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.953   0.246   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.083   1.521   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0      -6.283  -1.052   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.703   1.591   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.787  -0.237   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.508  -2.376   0.000  0.00  0.00           O+0
HETATM   26 Cl   UNK     0      11.105   0.000   0.000  0.00  0.00          Cl-1
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4   12                                                       
CONECT    4    3   17                                                       
CONECT    5    6   13                                                       
CONECT    6    5   21                                                       
CONECT    7   12   16                                                       
CONECT    8   13   18                                                       
CONECT    9   14   19                                                       
CONECT   10   15   21                                                       
CONECT   11   24   25                                                       
CONECT   12    3    7   15                                                  
CONECT   13    5    8   14                                                  
CONECT   14    9   13   16                                                  
CONECT   15   10   12   20                                                  
CONECT   16    7   14   21                                                  
CONECT   17    4   20   22                                                  
CONECT   18    8   19   24                                                  
CONECT   19    9   18   25                                                  
CONECT   20   15   17   23                                                  
CONECT   21    6   10   16                                                  
CONECT   22    1   17                                                       
CONECT   23    2   20                                                       
CONECT   24   11   18                                                       
CONECT   25   11   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Berberine chloride hydrate	HMDB

Chemical Formula

C₂₀H₁₈ClNO₄

Average Mass

371.8140 Da

Monoisotopic Mass

371.09244 Da

IUPAC Name

16,17-dimethoxy-5,7-dioxa-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium chloride

Traditional Name

berberine chloride

CAS Registry Number

633-65-8

SMILES

[Cl-].COC1=C(OC)C2=C[N+]3=C(C=C2C=C1)C1=CC2=C(OCO2)C=C1CC3

InChI Identifier

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

InChI Key

VKJGBAJNNALVAV-UHFFFAOYSA-M

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

Not Available

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
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organic chloride salt
Organopnictogen compound
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:31271 )

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	-0.41	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	36.89 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

HMDB0041837

DrugBank ID

DBSALT002313

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C12679

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12456

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Berberine hydrochloride (NP0138601)

MOL for NP0138601 (Berberine hydrochloride)

3D MOL for NP0138601 (Berberine hydrochloride)

3D SDF for NP0138601 (Berberine hydrochloride)

3D-SDF for NP0138601 (Berberine hydrochloride)

PDB for NP0138601 (Berberine hydrochloride)

3D PDB for NP0138601 (Berberine hydrochloride)

SMILES for NP0138601 (Berberine hydrochloride)

INCHI for NP0138601 (Berberine hydrochloride)

Structure for NP0138601 (Berberine hydrochloride)

3D Structure for NP0138601 (Berberine hydrochloride)