NP-MRD: Showing NP-Card for 9-Berberoline (NP0068223)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 13:20:43 UTC

Updated at

2022-04-28 13:20:44 UTC

NP-MRD ID

NP0068223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Berberoline

Description

Berberrubine, also known as 6847-93-4 or 9-berberoline, 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. Berberrubine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Berberrubine has been detected, but not quantified in, fruits and tea. 9-Berberoline is found in Berberis actinacantha, Berberis amurensis , Berberis darwinii , Berberis iliensis, Berberis turcomanica, Berberis valdiviana, Berberis vulgaris , Coscinium fenestratum (Gaertn.)Colebr. , Fibraurea chloroleuca Miers, Fibraurea chloroleuca Miore., Thalictrum glandulosissimum, Thalictrum polygamum Muhl and Thalictrum polyganum. 9-Berberoline was first documented in 2006 (PMID: 16730982). This could make berberrubine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
    6.6246    0.8320    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -0.0136   -0.3376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3597    0.1672   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    1.1237    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210    1.2975    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5949    0.4895    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459    0.6583    0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268   -0.1837   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710   -1.1311   -0.9041 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.1599   -1.2614   -1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -0.4679   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161   -0.6298   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8302   -1.6003   -1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146   -2.0276   -1.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -1.8950   -1.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325   -0.8659   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3173   -0.7345   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8292    0.2068    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    1.0390    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860    0.9015    1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573   -0.0415    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.8772    2.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0981    1.8541    1.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1367    0.5477    0.9574 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6638    0.6787    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6315    0.6604   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    1.8818    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    1.7472    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    2.0721    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    1.4248    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496   -2.0254   -1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -1.7597   -1.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -2.0060   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6995   -3.0730   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9287   -1.6342   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233   -2.8705   -1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0048   -1.3864   -0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344    1.5526    1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1746    2.6423    0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8232    1.9534    2.3661 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
 12 11  1  0
 11  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 24  1  0
 24 23  1  0
 23 22  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14  9  1  0
  9 10  2  0
  4  3  1  0
  9  8  1  0
 10 11  1  0
 16 21  1  0
 22 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 13 32  1  0
  5 29  1  0
  4 28  1  0
  7 30  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 17 37  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  0
 14 34  1  0
 10 31  1  0
M  CHG  1   9   1
M  END


  Mrv1652305171805372D          

 24 28  0  0  0  0            999 V2000
    1.9804   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804   -0.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6908   -0.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6908   -1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242   -1.2448    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.4075   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4138   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -1.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8472   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305   -2.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -3.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534   -4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639   -3.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5576   -2.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699   -1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637   -0.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -0.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904   -1.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2680   -2.4707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806   -4.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2869   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1  4  2  0  0  0  0
  2  3  2  0  0  0  0
  2 18  1  0  0  0  0
  3  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 23  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  2  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0068223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(C=C1)C=C1C3=CC4=C(OCO4)C=C3CC[N+]1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1

> <INCHI_KEY>
GLYPKDKODVRYGP-UHFFFAOYSA-O

> <FORMULA>
C19H16NO4

> <MOLECULAR_WEIGHT>
322.3346

> <EXACT_MASS>
322.107933005

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.89521097604788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-hydroxy-17-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15(20),16,18-octaen-13-ylium

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-1.4292063418050789

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.271586535140377

> <JCHEM_PKA_STRONGEST_BASIC>
-4.519862373583301

> <JCHEM_POLAR_SURFACE_AREA>
51.8

> <JCHEM_REFRACTIVITY>
89.04100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-17-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15(20),16,18-octaen-13-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       3.697  -3.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.697  -0.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.023  -0.786   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.023  -2.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.698  -0.775   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.349   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.698  -2.324   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0       6.361  -3.098   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.372  -4.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.036  -3.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.048  -4.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.710  -5.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.722  -6.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.060  -7.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.386  -6.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.374  -5.387   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.371  -2.324   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.359  -0.786   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.904  -0.317   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -1.573   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.915  -2.805   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.700  -4.612   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.724  -7.687   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.736  -9.212   0.000  0.00  0.00           C+0
CONECT    1   17    4                                                       
CONECT    2    3   18                                                       
CONECT    3    2    6    4                                                  
CONECT    4    1    3    8                                                  
CONECT    5    7    6                                                       
CONECT    6    3    5                                                       
CONECT    7    5    8   10                                                  
CONECT    8    4    7    9                                                  
CONECT    9    8   12                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12    9   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   11   15   22                                                  
CONECT   17    1   18   21                                                  
CONECT   18    2   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   17   20                                                       
CONECT   22   16                                                            
CONECT   23   15   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
6847-93-4	HMDB
9-Berberoline	HMDB
9-Berberoline chloride	MeSH
Berberrubine chloride	MeSH
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride	MeSH
Berberrubine	MeSH

Chemical Formula

C₁₉H₁₆NO₄

Average Mass

322.3346 Da

Monoisotopic Mass

322.10793 Da

IUPAC Name

16-hydroxy-17-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15(20),16,18-octaen-13-ylium

Traditional Name

16-hydroxy-17-methoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15(20),16,18-octaen-13-ylium

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(C=C1)C=C1C3=CC4=C(OCO4)C=C3CC[N+]1=C2

InChI Identifier

InChI=1S/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1

InChI Key

GLYPKDKODVRYGP-UHFFFAOYSA-O

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
Berberis actinacantha	Plant	KNApSAcK
Berberis amurensis	Plant	KNApSAcK
Berberis darwinii	Plant	KNApSAcK
Berberis iliensis	Plant	KNApSAcK
Berberis turcomanica	Plant	KNApSAcK
Berberis valdiviana	Plant	KNApSAcK
Berberis vulgaris	Plant	KNApSAcK
Coscinium fenestratum	Plant	KNApSAcK
Fibraurea chloroleuca	Plant	KNApSAcK
Fibraurea chloroleuca Miore.	Plant	KNApSAcK
Thalictrum glandulosissimum	Plant	KNApSAcK
Thalictrum polygamum Muhl	Plant	KNApSAcK
Thalictrum polyganum	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
1-hydroxy-4-unsubstituted benzenoid
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	-0.31	ALOGPS
logP	-1.4	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.04 m³·mol⁻¹	ChemAxon
Polarizability	34.9 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

HMDB0030266

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002095

KNApSAcK ID

C00026111

Chemspider ID

65548

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72704

PDB ID

Not Available

ChEBI ID

441632

Good Scents ID

Not Available

References

General References

Park KD, Lee JH, Kim SH, Kang TH, Moon JS, Kim SU: Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents. Bioorg Med Chem Lett. 2006 Aug 1;16(15):3913-6. doi: 10.1016/j.bmcl.2006.05.033. Epub 2006 May 30. [PubMed:16730982 ]

Showing NP-Card for 9-Berberoline (NP0068223)

MOL for NP0068223 (9-Berberoline)

3D MOL for NP0068223 (9-Berberoline)

3D SDF for NP0068223 (9-Berberoline)

3D-SDF for NP0068223 (9-Berberoline)

PDB for NP0068223 (9-Berberoline)

3D PDB for NP0068223 (9-Berberoline)

SMILES for NP0068223 (9-Berberoline)

INCHI for NP0068223 (9-Berberoline)

Structure for NP0068223 (9-Berberoline)

3D Structure for NP0068223 (9-Berberoline)