NP-MRD: Showing NP-Card for (+)-Predicentrine (NP0068148)

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Record Information

Version

2.0

Created at

2022-04-28 13:09:02 UTC

Updated at

2022-04-28 13:09:02 UTC

NP-MRD ID

NP0068148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Predicentrine

Description

Predicentrine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. (+)-Predicentrine is found in Annona purpurea , Cassytha filiformis , Corydalis cava , Corydalis solida, Desmos rostrata, Dicentra peregrina, Glaucium corniculatum, Glaucium leiocarpum, Liriodendron tulipifera, Magnolia elegans, Ocotea brachybotra, Ocotea macropoda, Ocotea vellosiana, Ocotea velloziana, Platycapnos spicata and Strychnopsis thouarsii Baill.. (+)-Predicentrine was first documented in 2006 (PMID: 16924583). Based on a literature review a small amount of articles have been published on Predicentrine (PMID: 34684698) (PMID: 19053513) (PMID: 17391965) (PMID: 33635585).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215092D          

 25 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    4.1471    3.5557   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    2.1643   -0.4616 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    1.3769   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8858    2.0071   -0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    1.2671    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150   -0.1085    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0076   -0.7643   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1605    0.0077   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3979   -0.5959   -0.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -2.0058   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141   -0.8949    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780   -2.2267    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -3.0090    0.4718 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204   -3.7387   -0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5773   -2.8647    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195   -4.2247    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.1593    1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7903   -0.8154    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -0.1776    0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028    1.1982   -0.0924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5477    2.0068    0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327    1.8865   -0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321    2.6136   -1.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479    1.3854    0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609   -0.0983    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    3.9955    0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    3.8718   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958    3.9562   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    3.0934   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914   -1.8039    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8478   -2.4065   -1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138   -2.4048    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5240   -2.3644   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -4.5965   -0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890   -4.1255   -1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134   -3.0585   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -4.7709    1.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6307   -2.7274    1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5155    1.0995   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    3.0060   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808    2.1263    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0419    3.4427   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288    3.1560   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430    2.0207   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7912    1.7513    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9310    1.8002    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5136   -0.3845    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7998   -0.4622    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 21  1  0
 21 20  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 18  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
 11 19  1  0
  5  4  2  0
  4  3  1  0
 11  6  1  0
 19 20  1  0
 19 18  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
  7 30  1  0
 21 40  1  0
 21 41  1  0
 20 39  1  6
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 17 38  1  0
 16 37  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
  4 29  1  0
M  END


  Mrv1652304282215092D          

 25 28  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  1  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(C[C@@H]3N(C)CCC4=CC(O)=C(OC)C2=C34)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-21-6-5-11-8-15(22)20(25-4)19-13-10-17(24-3)16(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1

> <INCHI_KEY>
OUTYMWDDJORZOH-AWEZNQCLSA-N

> <FORMULA>
C20H23NO4

> <MOLECULAR_WEIGHT>
341.407

> <EXACT_MASS>
341.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.76656755207104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-4,5,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.924832909

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.87326381322618

> <JCHEM_PKA_STRONGEST_BASIC>
7.022007286105548

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
97.39679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-4,5,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

> <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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17                                                            
CONECT   19   12                                                            
CONECT   20   11   21                                                       
CONECT   21   20                                                            
CONECT   22    2   23                                                       
CONECT   23   22                                                            
CONECT   24    1   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₄

Average Mass

341.4070 Da

Monoisotopic Mass

341.16271 Da

IUPAC Name

(9S)-4,5,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

Traditional Name

(9S)-4,5,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(C[C@@H]3N(C)CCC4=CC(O)=C(OC)C2=C34)=C1

InChI Identifier

InChI=1S/C20H23NO4/c1-21-6-5-11-8-15(22)20(25-4)19-13-10-17(24-3)16(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1

InChI Key

OUTYMWDDJORZOH-AWEZNQCLSA-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
Annona purpurea	Plant	KNApSAcK
Cassytha filiformis	Plant	KNApSAcK
Corydalis cava	Plant	KNApSAcK
Corydalis solida	LOTUS Database	35616633
Desmos rostrata	Plant	KNApSAcK
Dicentra peregrina	LOTUS Database	35616633
Glaucium corniculatum	LOTUS Database	35616633
Glaucium leiocarpum	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Magnolia elegans	LOTUS Database	35616633
Ocotea brachybotra	Plant	KNApSAcK
Ocotea macropoda	Plant	KNApSAcK
Ocotea vellosiana	Plant	KNApSAcK
Ocotea velloziana	LOTUS Database	35616633
Platycapnos spicata	Plant	KNApSAcK
Strychnopsis thouarsii Baill.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
2-naphthol
Naphthalene
Tetrahydroisoquinoline
Quinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Organoheterocyclic compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
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	2.88	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	7.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	37.77 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

C00026016

Chemspider ID

8218506

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10042942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang FX, Zhu N, Zhou F, Lin DX: Natural Aporphine Alkaloids with Potential to Impact Metabolic Syndrome. Molecules. 2021 Oct 10;26(20). pii: molecules26206117. doi: 10.3390/molecules26206117. [PubMed:34684698 ]
Nguyen NT, Pham VC, Litaudon M, Gueritte F, Grellier P, Nguyen VT, Nguyen VH: Antiplasmodial alkaloids from Desmos rostrata. J Nat Prod. 2008 Dec;71(12):2057-9. doi: 10.1021/np8004437. [PubMed:19053513 ]
Iturriaga-Vasquez P, Perez EG, Slater EY, Bermudez I, Cassels BK: Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. Bioorg Med Chem. 2007 May 15;15(10):3368-72. doi: 10.1016/j.bmc.2007.03.023. Epub 2007 Mar 13. [PubMed:17391965 ]
Barbosa H, Costa-Silva TA, Alves Conserva GA, Araujo AJ, Lordello ALL, Antar GM, Amaral M, Soares MG, Tempone AG, Lago JHG: Aporphine Alkaloids from Ocotea puberula with Anti-Trypanosoma Cruzi Potential - Activity of Dicentrine-beta-N-Oxide in the Plasma Membrane Electric Potentials. Chem Biodivers. 2021 Apr;18(4):e2001022. doi: 10.1002/cbdv.202001022. Epub 2021 Mar 1. [PubMed:33635585 ]
Chi TC, Lee SS, Su MJ: Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats. Planta Med. 2006 Oct;72(13):1175-80. doi: 10.1055/s-2006-947199. Epub 2006 Aug 21. [PubMed:16924583 ]

Showing NP-Card for (+)-Predicentrine (NP0068148)

MOL for NP0068148 ((+)-Predicentrine)

3D MOL for NP0068148 ((+)-Predicentrine)

3D SDF for NP0068148 ((+)-Predicentrine)

3D-SDF for NP0068148 ((+)-Predicentrine)

PDB for NP0068148 ((+)-Predicentrine)

3D PDB for NP0068148 ((+)-Predicentrine)

SMILES for NP0068148 ((+)-Predicentrine)

INCHI for NP0068148 ((+)-Predicentrine)

Structure for NP0068148 ((+)-Predicentrine)

3D Structure for NP0068148 ((+)-Predicentrine)