NP-MRD: Showing NP-Card for (+)-Scandine (NP0066823)

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Record Information

Version

2.0

Created at

2022-04-28 11:03:27 UTC

Updated at

2022-04-28 11:03:27 UTC

NP-MRD ID

NP0066823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Scandine

Description

Scandine belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane. (+)-Scandine is found in Kopsia sp., Melodinus fusiformis, Melodinus hemsleyanus, Melodinus henryi, Melodinus scandens and Melodinus tenuicaudatus. (+)-Scandine was first documented in 2016 (PMID: 26727144). Based on a literature review a small amount of articles have been published on Scandine (PMID: 28948736) (PMID: 33556841) (PMID: 32955264) (PMID: 29933711).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213032D          

 26 30  0  0  1  0            999 V2000
   -0.0412   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -0.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842   -1.6041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9682   -1.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7555   -0.2242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9131   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -1.3967    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5730   -2.2114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7580   -2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -2.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -3.5459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -2.4364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1140   -1.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -1.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033   -0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144   -0.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586   -3.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324   -3.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -3.2207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -4.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357   -2.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504   -2.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 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
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  1  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    3.6493    0.7544    1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6348    0.0166    1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916    0.3363    0.1059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9058    0.6744   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1846   -0.1408   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -1.4203   -1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -1.3924   -1.4889 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771   -0.7434   -2.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.0987   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570   -0.2253   -0.2408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4099   -1.2122    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -2.1321   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -3.0453    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911   -3.1046    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -2.1865    2.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -1.2567    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -0.3466    2.6144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321    0.6297    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6117    1.1877    2.7946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    1.0010    0.6315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3361    2.0150    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0417    2.3309    1.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363    2.6881   -0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663    3.6537   -0.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    1.5975    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -0.7703   -0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9712    1.6087    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1736    0.5080    2.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -0.8306    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3958    1.6566   -0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    0.1209   -2.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895   -2.1945   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4465   -1.7159   -3.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -0.1460   -3.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840   -1.5608   -3.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    0.1126   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945    1.1688   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910   -2.1615   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3897   -3.7513   -0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -3.8362    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7741   -2.2271    3.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.3359    3.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561    4.6325   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9960    3.8570   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027    3.2730   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    2.2100   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452    2.1534    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9861   -1.5495    0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 20 21  1  1
 20 25  1  0
  3 25  1  1
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 26  1  0
 10 11  1  0
 11 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 10 20  1  0
 12 11  1  0
 18 20  1  0
 26  3  1  0
 26  7  1  0
 24 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
  2 29  1  0
  1 27  1  0
  1 28  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 26 48  1  1
 17 42  1  0
 15 41  1  0
 14 40  1  0
 13 39  1  0
 12 38  1  0
M  END


  Mrv1652304282213032D          

 26 30  0  0  1  0            999 V2000
   -0.0412   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -0.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842   -1.6041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9682   -1.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7555   -0.2242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9131   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -1.3967    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5730   -2.2114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7580   -2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -2.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836   -3.5459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -2.4364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1140   -1.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -1.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033   -0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144   -0.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586   -3.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324   -3.7435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -3.2207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -4.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357   -2.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504   -2.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 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
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  1  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0066823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12C[C@]3(C=C)C=CCN4CC[C@]1([C@H]34)C1=C(NC2=O)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c1-3-19-9-6-11-23-12-10-20(16(19)23)14-7-4-5-8-15(14)22-17(24)21(20,13-19)18(25)26-2/h3-9,16H,1,10-13H2,2H3,(H,22,24)/t16-,19-,20+,21+/m0/s1

> <INCHI_KEY>
JTSSMMKHJYRYEG-VRXWPRPYSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.620838162763775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,10R,12S,19S)-12-ethenyl-9-oxo-8,16-diazapentacyclo[10.6.1.0^{1,10}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.1740935906666654

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.056434787134986

> <JCHEM_PKA_STRONGEST_BASIC>
8.333006029955708

> <JCHEM_POLAR_SURFACE_AREA>
58.64

> <JCHEM_REFRACTIVITY>
100.42770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,10R,12S,19S)-12-ethenyl-9-oxo-8,16-diazapentacyclo[10.6.1.0^{1,10}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

> <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      -0.077  -0.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.167  -1.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -2.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.717  -2.994   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.807  -1.906   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.410  -0.419   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.571  -0.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.269  -1.519   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.179  -2.607   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.936  -4.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.415  -4.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.132  -5.098   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.889  -6.619   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.570  -4.548   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.813  -3.027   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.617  -2.057   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.860  -0.536   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.298   0.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494  -0.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.251  -2.477   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.536  -5.615   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.234  -6.988   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.048  -6.012   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.648  -7.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.253  -4.190   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.774  -3.948   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11   25                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10   16                                             
CONECT   10    9   11   12   21                                             
CONECT   11   10    4                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   10   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    4   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂N₂O₃

Average Mass

350.4180 Da

Monoisotopic Mass

350.16304 Da

IUPAC Name

methyl (1S,10R,12S,19S)-12-ethenyl-9-oxo-8,16-diazapentacyclo[10.6.1.0^{1,10}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

Traditional Name

methyl (1S,10R,12S,19S)-12-ethenyl-9-oxo-8,16-diazapentacyclo[10.6.1.0^{1,10}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12C[C@]3(C=C)C=CCN4CC[C@]1([C@H]34)C1=C(NC2=O)C=CC=C1

InChI Identifier

InChI=1S/C21H22N2O3/c1-3-19-9-6-11-23-12-10-20(16(19)23)14-7-4-5-8-15(14)22-17(24)21(20,13-19)18(25)26-2/h3-9,16H,1,10-13H2,2H3,(H,22,24)/t16-,19-,20+,21+/m0/s1

InChI Key

JTSSMMKHJYRYEG-VRXWPRPYSA-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
Kopsia sp.	Plant	KNApSAcK
Melodinus fusiformis	Plant	KNApSAcK
Melodinus hemsleyanus	Plant	KNApSAcK
Melodinus henryi	Plant	KNApSAcK
Melodinus scandens	Plant	KNApSAcK
Melodinus tenuicaudatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melodinus alkaloids. These are alkaloids with a structure that is based on the melodinus skeleton. This backbone is a pentacyclic structure that contains a tetrahydroquinoline and an indolizine joined to each other through a cyclopentane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Melodinus alkaloids

Sub Class

Not Available

Direct Parent

Melodinus alkaloids

Alternative Parents

Substituents

Melodinus skeleton
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Cyclic carboximidic acid
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxygen 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	2.63	ALOGPS
logP	2.17	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	8.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.43 m³·mol⁻¹	ChemAxon
Polarizability	36.62 Å³	ChemAxon
Number of Rings	5	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

C00024473

Chemspider ID

24736249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12082288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lu Y, Shen NT, Yu HY: [Studies on alkaloids from Melodinus moraei]. Zhongguo Zhong Yao Za Zhi. 2017 Jan;42(2):307-310. doi: 10.19540/j.cnki.cjcmm.20161222.006. [PubMed:28948736 ]
Li FR, Liu L, Liu YP, Wang JT, Yang ML, Khan A, Qin XJ, Wang YD, Cheng GG: HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities. Phytochemistry. 2021 Apr;184:112673. doi: 10.1016/j.phytochem.2021.112673. Epub 2021 Feb 5. [PubMed:33556841 ]
Wu J, Zhao SM, Shi BB, Bao MF, Schinnerl J, Cai XH: Cage-Monoterpenoid Quinoline Alkaloids with Neurite Growth Promoting Effects from the Fruits of Melodinus yunnanensis. Org Lett. 2020 Oct 2;22(19):7676-7680. doi: 10.1021/acs.orglett.0c02871. Epub 2020 Sep 21. [PubMed:32955264 ]
Yu JQ, Sun XW, Wang ZW, Fang L, Wang X: Alkaloids from Melodinus henryi with anti-inflammatory activity. J Asian Nat Prod Res. 2019 Aug;21(8):820-825. doi: 10.1080/10286020.2018.1482878. Epub 2018 Jun 22. [PubMed:29933711 ]
Xiao JA, Xia PJ, Zhang XY, Chen XQ, Ou GC, Yang H: Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (+/-)-scandine. Chem Commun (Camb). 2016 Feb 4;52(10):2177-80. doi: 10.1039/c5cc07485a. [PubMed:26727144 ]

Showing NP-Card for (+)-Scandine (NP0066823)

MOL for NP0066823 ((+)-Scandine)

3D MOL for NP0066823 ((+)-Scandine)

3D SDF for NP0066823 ((+)-Scandine)

3D-SDF for NP0066823 ((+)-Scandine)

PDB for NP0066823 ((+)-Scandine)

3D PDB for NP0066823 ((+)-Scandine)

SMILES for NP0066823 ((+)-Scandine)

INCHI for NP0066823 ((+)-Scandine)

Structure for NP0066823 ((+)-Scandine)

3D Structure for NP0066823 ((+)-Scandine)