NP-MRD: Showing NP-Card for (+)-Xanthoplanine (NP0069030)

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Record Information

Version

2.0

Created at

2022-04-28 14:17:51 UTC

Updated at

2022-04-28 14:17:51 UTC

NP-MRD ID

NP0069030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Xanthoplanine

Description

Xanthoplanine 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. (+)-Xanthoplanine is found in Dehaasia incrassata, Dehaasia triandra, Litsea cubeba , Thalictrum foliolosum , Xylopia parviflora and Zanthoxylum planispinum. (+)-Xanthoplanine was first documented in 2004 (PMID: 15081299). Based on a literature review a small amount of articles have been published on Xanthoplanine (PMID: 32142888) (PMID: 17391965).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216172D          

 26 29  0  0  1  0            999 V2000
    4.2868    0.8250    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
    3.5724   -0.4125    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
    2.8579    0.8250    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
    2.1434    1.2375    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 22  1  0  0  0  0
 11 23  1  0  0  0  0
  2 24  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  1  11   1
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.2452    0.7208   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027   -0.6197   -0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6148   -1.0666   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6574   -0.1437   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3649   -0.5470   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9776   -1.8609   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480   -2.7646   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -2.3826   -0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2209   -3.2847   -1.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -2.4262   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3688   -1.5127    0.4326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9066   -0.1312    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8524    0.7393    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5978    2.0502    1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371    2.5272    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    3.8818    1.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574    4.7365    1.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636    1.6814    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625    2.3119    0.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    3.0308   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    0.3691    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2042    0.1171    1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.5228    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599   -1.6047   -0.2404 N   0  0  1  0  0  4  0  0  0  0  0  0
   -2.5091   -1.7269   -1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366   -2.8359    0.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9868    1.0647    0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3267    0.9181   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085    1.4174   -1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0180    0.8230   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7195   -3.8065   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819   -3.0166   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -3.3699    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -2.8334   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5920   -1.8937    1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    2.7099    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525    5.7229    2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736    4.7453    1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    4.2885    2.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829    3.0774   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385    4.0574   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    2.4943   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    0.8830    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039   -0.6953    2.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487    0.2515   -0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -0.8880    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139   -1.2917   -2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.1962   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230   -2.8127   -1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -3.6670   -0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967   -3.0143    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -2.7040    0.1477 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
  8  7  1  0
  7  6  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 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
 13 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 21  5  1  0
  5  4  2  0
  4  3  1  0
  5  6  1  0
 24 11  1  0
 13 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 32  1  0
  7 31  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  1
 20 40  1  0
 20 41  1  0
 20 42  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 14 36  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
  4 30  1  0
M  CHG  1  24   1
M  END


  Mrv1652304282216172D          

 26 29  0  0  1  0            999 V2000
    4.2868    0.8250    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
    3.5724   -0.4125    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
    2.8579    0.8250    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
    2.1434    1.2375    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 22  1  0  0  0  0
 11 23  1  0  0  0  0
  2 24  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  CHG  1  11   1
M  END
> <DATABASE_ID>
NP0069030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C[C@H]3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO4/c1-22(2)7-6-12-10-18(25-4)21(26-5)20-14-11-17(24-3)16(23)9-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/p+1/t15-/m0/s1

> <INCHI_KEY>
FGUCOPALAZXICJ-HNNXBMFYSA-O

> <FORMULA>
C21H26NO4

> <MOLECULAR_WEIGHT>
356.441

> <EXACT_MASS>
356.185634741

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.81571511244185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
-1.237503707471745

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.597711922587397

> <JCHEM_PKA_STRONGEST_BASIC>
-4.423959165772149

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
113.31039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-03 g/l

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

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.057  -2.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.611  -2.130   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   22   23                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   11                                                            
CONECT   23   11                                                            
CONECT   24    2                                                            
CONECT   25    1   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(6AS)-1,2,10-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinolin-6-ium-9-ol	MeSH

Chemical Formula

C₂₁H₂₆NO₄

Average Mass

356.4410 Da

Monoisotopic Mass

356.18563 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C[C@H]3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C1

InChI Identifier

InChI=1S/C21H25NO4/c1-22(2)7-6-12-10-18(25-4)21(26-5)20-14-11-17(24-3)16(23)9-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/p+1/t15-/m0/s1

InChI Key

FGUCOPALAZXICJ-HNNXBMFYSA-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
Dehaasia incrassata	LOTUS Database	35616633
Dehaasia triandra	Plant	KNApSAcK
Litsea cubeba	Plant	KNApSAcK
Thalictrum foliolosum	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK
Zanthoxylum planispinum	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
Naphthalene
Tetrahydroisoquinoline
Quinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Amine
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	0.8	ALOGPS
logP	-1.2	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.31 m³·mol⁻¹	ChemAxon
Polarizability	39.82 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

C00027170

Chemspider ID

25042175

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14262868

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nishiyama Y, Moriyasu M, Ichimaru M, Iwasa K, Kato A, Mathenge SG, Chalo Mutiso PB, Juma FD: Quaternary isoquinoline alkaloids from Xylopia parviflora. Phytochemistry. 2004 Apr;65(7):939-44. doi: 10.1016/j.phytochem.2003.12.010. [PubMed:15081299 ]
Shi X, Pan S, Li Y, Ma W, Wang H, Xu C, Li L: Xanthoplanine attenuates macrophage polarization towards M1 and inflammation response via disruption of CrkL-STAT5 complex. Arch Biochem Biophys. 2020 Apr 15;683:108325. doi: 10.1016/j.abb.2020.108325. Epub 2020 Mar 3. [PubMed:32142888 ]
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 ]

Showing NP-Card for (+)-Xanthoplanine (NP0069030)

MOL for NP0069030 ((+)-Xanthoplanine)

3D MOL for NP0069030 ((+)-Xanthoplanine)

3D SDF for NP0069030 ((+)-Xanthoplanine)

3D-SDF for NP0069030 ((+)-Xanthoplanine)

PDB for NP0069030 ((+)-Xanthoplanine)

3D PDB for NP0069030 ((+)-Xanthoplanine)

SMILES for NP0069030 ((+)-Xanthoplanine)

INCHI for NP0069030 ((+)-Xanthoplanine)

Structure for NP0069030 ((+)-Xanthoplanine)

3D Structure for NP0069030 ((+)-Xanthoplanine)