NP-MRD: Showing NP-Card for (-)-Capaurine (NP0050955)

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Record Information

Version

2.0

Created at

2022-04-27 22:25:29 UTC

Updated at

2022-04-27 22:25:29 UTC

NP-MRD ID

NP0050955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Capaurine

Description

Capaurine 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. (-)-Capaurine is found in Anomianthus dulcis , Corydalis aurea, Corydalis incisa, Corydalis micrantha, Corydalis montana, Corydalis pallida, Fibraurea recisa, Stephania lincangensis, Stephania pierrei and Uvaria dulcis. (-)-Capaurine was first documented in 2013 (PMID: 23713286). Based on a literature review very few articles have been published on Capaurine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200252D          

 27 30  0  0  1  0            999 V2000
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  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  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    6.4041    0.2588    1.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -0.0376    0.5567 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363   -0.0885    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456    0.1437    1.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861    0.0751    1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -0.2153    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5111   -0.4450   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.7355   -2.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -0.3855   -0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446   -0.6104   -1.8653 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1891    0.4033   -2.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528   -0.2556    0.1677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3870   -0.7085   -1.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8365   -0.8044   -0.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6085   -1.8443   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9793   -1.8954   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5099   -0.8504   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8727   -0.8173    0.0873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6754   -1.8787   -0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622    0.2101    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3150    1.2473    0.9556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    2.3676    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4037    0.2093   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5408    1.3272    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157    0.9749    0.7129 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    1.1273    2.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    0.3165    2.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9431   -0.4237    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3117    1.3218    2.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4871   -0.0557    1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    0.3721    2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5887   -0.8996   -2.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    1.1097   -3.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9805    1.0147   -2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6410   -0.1125   -3.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -1.0446    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447   -1.6953   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817    0.0307   -1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160   -2.6672   -1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6080   -2.6960   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1949   -2.8372   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7149   -1.8009   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7159   -1.9418   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485    2.2411   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    3.2915    0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8812    2.5021    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4751    2.0694   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    1.8920    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.7922    2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2569    2.2201    2.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -0.6565    3.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501    0.8848    3.3337 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 12  1  0
 12 13  1  0
 13 14  1  0
 14 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20 17  2  0
 17 18  1  0
 18 19  1  0
 17 16  1  0
 16 15  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9  3  1  0
 27  5  1  0
 25 12  1  0
 15 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 24 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 16 40  1  0
 15 39  1  0
  8 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
M  END


  Mrv1652304282200252D          

 27 30  0  0  1  0            999 V2000
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6555    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9058    0.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  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  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C([C@@H]3CC4=C(CN3CC2)C(OC)=C(OC)C=C4)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO5/c1-24-16-6-5-12-9-15-18-13(10-17(25-2)21(27-4)19(18)23)7-8-22(15)11-14(12)20(16)26-3/h5-6,10,15,23H,7-9,11H2,1-4H3/t15-/m0/s1

> <INCHI_KEY>
GSPIMPLJQOCBFY-HNNXBMFYSA-N

> <FORMULA>
C21H25NO5

> <MOLECULAR_WEIGHT>
371.433

> <EXACT_MASS>
371.173272909

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.026545307943266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-12-ol

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.844409398666667

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.254781089786762

> <JCHEM_PKA_STRONGEST_BASIC>
5.88579990530572

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
103.3364

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
capaurine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.862   2.807   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.870   3.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.415   0.188   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.424   1.352   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.399  -2.140   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.911  -2.431   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.375  -1.558   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.691   1.352   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.699   0.188   0.000  0.00  0.00           C+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    1                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Capaurine, (+-)-isomer	MeSH

Chemical Formula

C₂₁H₂₅NO₅

Average Mass

371.4330 Da

Monoisotopic Mass

371.17327 Da

IUPAC Name

(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-12-ol

Traditional Name

capaurine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C([C@@H]3CC4=C(CN3CC2)C(OC)=C(OC)C=C4)C(O)=C1OC

InChI Identifier

InChI=1S/C21H25NO5/c1-24-16-6-5-12-9-15-18-13(10-17(25-2)21(27-4)19(18)23)7-8-22(15)11-14(12)20(16)26-3/h5-6,10,15,23H,7-9,11H2,1-4H3/t15-/m0/s1

InChI Key

GSPIMPLJQOCBFY-HNNXBMFYSA-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
Anomianthus dulcis	Plant	KNApSAcK
Corydalis aurea	Plant	KNApSAcK
Corydalis incisa	LOTUS Database	35616633
Corydalis micrantha	Plant	KNApSAcK
Corydalis montana	Plant	KNApSAcK
Corydalis pallida	Plant	KNApSAcK
Fibraurea recisa	LOTUS Database	35616633
Stephania lincangensis	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Uvaria dulcis	LOTUS Database	35616633

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
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:3366 )
Isoquinoline alkaloids (C09371 )

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	2.67	ALOGPS
logP	2.84	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	5.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.34 m³·mol⁻¹	ChemAxon
Polarizability	41.03 Å³	ChemAxon
Number of Rings	4	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

C00001829

Chemspider ID

84966

KEGG Compound ID

C09371

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94149

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zuo AX, Li L, Ma YS, Rao GX: [Akaloids from roots of Stephania dentifolia]. Zhongguo Zhong Yao Za Zhi. 2013 Feb;38(4):574-7. [PubMed:23713286 ]

Showing NP-Card for (-)-Capaurine (NP0050955)

MOL for NP0050955 ((-)-Capaurine)

3D MOL for NP0050955 ((-)-Capaurine)

3D SDF for NP0050955 ((-)-Capaurine)

3D-SDF for NP0050955 ((-)-Capaurine)

PDB for NP0050955 ((-)-Capaurine)

3D PDB for NP0050955 ((-)-Capaurine)

SMILES for NP0050955 ((-)-Capaurine)

INCHI for NP0050955 ((-)-Capaurine)

Structure for NP0050955 ((-)-Capaurine)

3D Structure for NP0050955 ((-)-Capaurine)