NP-MRD: Showing NP-Card for Jatrorrhizine (NP0050992)

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Record Information

Version

2.0

Created at

2022-04-27 22:27:02 UTC

Updated at

2022-04-27 22:27:02 UTC

NP-MRD ID

NP0050992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jatrorrhizine

Description

3,4,11-Trimethoxy-10-oxo-6,7,8,10-tetrahydro-6-azatetraphen-6-ium 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. Jatrorrhizine is found in Acangelisia gusanlung, Archangelicia flava, Berberis aemulans, Berberis amurensis , Berberis cratagina, Berberis diaphana, Berberis dubia, Berberis heterobotrys, Berberis julianae, Berberis poiretii, Berberis poirettii, Berberis potaninii, Berberis pruinosa, Berberis spp., Berberis thunbergii , Berberis turcomanica, Berberis vulgaris , Chelidonum majus, Cineraria deltoidea, Coptis chinensis , Coptis chinensis var.brevisepala , Coptis deltoidea , Coptis gulinensis, Coptis japonica , Coptis linearisepala, Coptis omeiensis, Coptis quinquefolia, Coptis teeta , Coptis teetoides, Corydalis lutea, Enantia chlorantha , Fibraurea chloroleuca, Fibraurea recisa, Fibraurea tinctoria, Glaucium arabicum, Jateorhiza palmata , Magnolia biondii , Mahonia aquifolium, Mahonia bealei, Mahonia bodinieri, Mahonia confusa, Mahonia eurybracteata, Mahonia fortunei, Mahonia gracilipes, Mahonia japonica, Mahonia nepalensis , Mahonia shenii, Mahonia spp., Mahonia veitchiorum, Michelia spp., Nandina domestica , Papaver bracteatum , Phellodendron amurense , Stephania tetrandra , Stephania viridiflavens, Thalictrum atriplex, Thalictrum faberi, Thalictrum foliolosum , Thalictrum glandulosissimum, Thalictrum honanenae, Thalictrum honanense, Thalictrum lucidum, Thalictrum microgynum, Thalictrum minus, Thalictrum thunbergii, Thalictrum petaloideum, Thalictrum simplex, Thalictrum spp., Tinospora hainanensis , Xylopia parviflora and Zanthoxylum chaylbeum. 3,4,11-Trimethoxy-10-oxo-6,7,8,10-tetrahydro-6-azatetraphen-6-ium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502292D          

 25 28  0  0  0  0            999 V2000
    2.2221   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
  9 22  2  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
M  CHG  1   9   1
M  END

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    4.7682    2.5114    1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691    1.2870    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4437    0.2759    0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500    0.4469    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297   -0.5386   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -1.7068   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1860   -1.8916   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0052   -0.8898   -0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4001   -1.0895   -0.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830   -2.8048   -1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5257   -2.6100   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -1.3688   -0.7004 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3598   -1.2134   -0.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9892   -0.0709   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591    0.0723   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1366   -0.9482   -0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952   -1.9180    0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9313    1.2474    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077    1.3694    0.0422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8790    2.5794    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    2.2664    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331    2.1177    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859    0.9404    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    0.7968    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945   -0.3745   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976    3.0628    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906    2.3501    1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6190    3.1256    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    1.3789    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408   -2.8269   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9636   -0.3329    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2811   -3.7925   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -2.9576   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -3.4091   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -2.8938   -2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9918   -2.0179   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5957   -2.2946   -0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -2.7837    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6358   -1.5164    1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4834    2.8883    1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9787    2.5044    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6470    3.3553   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5530    3.1873    0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816    2.8875    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    1.5991    0.5645 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 10  1  0
 10 11  1  0
 11 12  1  0
 12 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 25  5  1  0
 14 23  1  0
 13 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 24 45  1  0
 22 44  1  0
 21 43  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 13 36  1  0
  7 30  1  0
  9 31  1  0
M  CHG  1  12   1
M  END


  Mrv1533004241502292D          

 25 28  0  0  0  0            999 V2000
    2.2221   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
  9 22  2  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
M  CHG  1   9   1
M  END
> <DATABASE_ID>
NP0050992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(CC[N+]3=C2C=C2C=CC(OC)=C(OC)C2=C3)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

> <INCHI_KEY>
MXTLAHSTUOXGQF-UHFFFAOYSA-O

> <FORMULA>
C20H20NO4

> <MOLECULAR_WEIGHT>
338.382

> <EXACT_MASS>
338.138684548

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.32944554827526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-hydroxy-3,4,11-trimethoxy-7,8-dihydro-6λ⁵-azatetraphen-6-ylium

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-1.367782340805079

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.227658179815505

> <JCHEM_PKA_STRONGEST_BASIC>
-4.440584572473525

> <JCHEM_POLAR_SURFACE_AREA>
51.8

> <JCHEM_REFRACTIVITY>
96.20050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
jatrorrhizine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.148  -7.051   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.660  -6.760   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.197  -1.813   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.734  -0.940   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.246  -0.649   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.254  -1.813   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.644  -4.432   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5    9                                                  
CONECT   23    6   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
Jatrorrhizine chloride	MeSH

Chemical Formula

C₂₀H₂₀NO₄

Average Mass

338.3820 Da

Monoisotopic Mass

338.13868 Da

IUPAC Name

10-hydroxy-3,4,11-trimethoxy-7,8-dihydro-6λ⁵-azatetraphen-6-ylium

Traditional Name

jatrorrhizine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CC[N+]3=C2C=C2C=CC(OC)=C(OC)C2=C3)C=C1O

InChI Identifier

InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

InChI Key

MXTLAHSTUOXGQF-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
Acangelisia gusanlung	Plant	KNApSAcK
Archangelicia flava	-	KNApSAcK
Berberis aemulans	Plant	KNApSAcK
Berberis amurensis	Plant	KNApSAcK
Berberis cratagina	Plant	KNApSAcK
Berberis diaphana	Plant	KNApSAcK
Berberis dubia	Plant	KNApSAcK
Berberis heterobotrys	Plant	KNApSAcK
Berberis julianae	Plant	KNApSAcK
Berberis poiretii	Plant	KNApSAcK
Berberis poirettii	Plant	KNApSAcK
Berberis potaninii	Plant	KNApSAcK
Berberis pruinosa	Plant	KNApSAcK
Berberis spp.	Plant	KNApSAcK
Berberis thunbergii	Plant	KNApSAcK
Berberis turcomanica	Plant	KNApSAcK
Berberis vulgaris	Plant	KNApSAcK
Chelidonum majus	-	KNApSAcK
Cineraria deltoidea	Plant	KNApSAcK
Coptis chinensis	Plant	KNApSAcK
Coptis chinensis var.brevisepala	Plant	KNApSAcK
Coptis deltoidea	Plant	KNApSAcK
Coptis gulinensis	Plant	KNApSAcK
Coptis japonica	Plant	KNApSAcK
Coptis linearisepala	Plant	KNApSAcK
Coptis omeiensis	Plant	KNApSAcK
Coptis quinquefolia	Plant	KNApSAcK
Coptis teeta	Plant	KNApSAcK
Coptis teetoides	Plant	KNApSAcK
Corydalis lutea	Plant	KNApSAcK
Enantia chlorantha	Plant	KNApSAcK
Fibraurea chloroleuca	Plant	KNApSAcK
Fibraurea recisa	Plant	KNApSAcK
Fibraurea tinctoria	Plant	KNApSAcK
Glaucium arabicum	Plant	KNApSAcK
Jateorhiza palmata	Plant	KNApSAcK
Magnolia biondii	Plant	KNApSAcK
Mahonia aquifolium	Plant	KNApSAcK
Mahonia bealei	Plant	KNApSAcK
Mahonia bodinieri	Plant	KNApSAcK
Mahonia confusa	Plant	KNApSAcK
Mahonia eurybracteata	Plant	KNApSAcK
Mahonia fortunei	Plant	KNApSAcK
Mahonia gracilipes	Plant	KNApSAcK
Mahonia japonica	Plant	KNApSAcK
Mahonia nepalensis	Plant	KNApSAcK
Mahonia shenii	Plant	KNApSAcK
Mahonia spp.	Plant	KNApSAcK
Mahonia veitchiorum	Plant	KNApSAcK
Michelia spp.	Plant	KNApSAcK
Nandina domestica	Plant	KNApSAcK
Papaver bracteatum	Plant	KNApSAcK
Phellodendron amurense	Plant	KNApSAcK
Stephania tetrandra	Plant	KNApSAcK
Stephania viridiflavens	Plant	KNApSAcK
Thalictrum atriplex	Plant	KNApSAcK
Thalictrum faberi	Plant	KNApSAcK
Thalictrum foliolosum	Plant	KNApSAcK
Thalictrum glandulosissimum	Plant	KNApSAcK
Thalictrum honanenae	Plant	KNApSAcK
Thalictrum honanense	Plant	KNApSAcK
Thalictrum lucidum	Plant	KNApSAcK
Thalictrum microgynum	Plant	KNApSAcK
Thalictrum minus	Plant	KNApSAcK
Thalictrum minus var. hypoleucum	Plant	KNApSAcK
Thalictrum petaloideum	Plant	KNApSAcK
Thalictrum simplex	Plant	KNApSAcK
Thalictrum spp.	Plant	KNApSAcK
Tinospora hainanensis	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK
Zanthoxylum chaylbeum	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
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyridinium
Pyridine
Heteroaromatic compound
Ether
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:6087 )
Isoquinoline alkaloids (C09553 )

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	0.02	ALOGPS
logP	-1.4	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	-4.4	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	3	ChemAxon
Refractivity	96.2 m³·mol⁻¹	ChemAxon
Polarizability	37.33 Å³	ChemAxon
Number of Rings	4	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

C00001874

Chemspider ID

Not Available

KEGG Compound ID

C09553

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72323

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Jatrorrhizine (NP0050992)

MOL for NP0050992 (Jatrorrhizine)

3D MOL for NP0050992 (Jatrorrhizine)

3D SDF for NP0050992 (Jatrorrhizine)

3D-SDF for NP0050992 (Jatrorrhizine)

PDB for NP0050992 (Jatrorrhizine)

3D PDB for NP0050992 (Jatrorrhizine)

SMILES for NP0050992 (Jatrorrhizine)

INCHI for NP0050992 (Jatrorrhizine)

Structure for NP0050992 (Jatrorrhizine)

3D Structure for NP0050992 (Jatrorrhizine)