NP-MRD: Showing NP-Card for Preakuammicine (NP0083366)

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Record Information

Version

2.0

Created at

2022-04-29 04:24:48 UTC

Updated at

2022-04-29 04:24:48 UTC

NP-MRD ID

NP0083366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Preakuammicine

Description

Preakuammicine belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. Preakuammicine is found in Alstonia scholaris , Alstonia angustiloba, Catharanthus roseus , Strempeliopsis strempelioides and Strychnos nux-vomica . Preakuammicine was first documented in 2006 (PMID: 16597153). Based on a literature review very few articles have been published on Preakuammicine (PMID: 28827772).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206242D          

 26 30  0  0  1  0            999 V2000
    1.8969   -1.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -0.8766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2419   -0.4570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1531    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.6300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2451    1.3078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541    1.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374    1.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4427    0.4245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3663   -0.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262   -0.8166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5754    1.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9687    0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329    0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6379    0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405   -1.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3327   -2.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738   -1.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -2.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 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
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    3.2743   -2.9772    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -3.2462   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256   -2.3926    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -2.7598   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -2.2052    0.0284 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -1.7327   -1.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7176   -0.4037   -1.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    0.1733   -0.0744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0701    0.8795    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    2.1317    0.0644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    2.4138    0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714    3.5965    0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    3.6476    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900    2.4327    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    1.2351    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660    1.2276    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2293    0.1045   -0.0746 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7210   -0.0639   -1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381    1.1695   -2.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    0.9655    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554    0.4588    1.6088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5711    2.2324    0.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    2.9661    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837   -1.1388    0.7586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1456   -1.0445    1.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -1.0152    0.8045 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7966   -2.2192   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937   -3.9119    0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -2.7588    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669   -4.1753   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5064   -3.8851   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -2.5683   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3023   -2.4400   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993   -1.6122   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452   -0.4496   -2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519    0.2074   -1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357    4.5548    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2853    4.5929    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4839    2.4339    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113    0.2921    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2206   -0.7631   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -0.4670   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938    1.1400   -2.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    4.0363    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5557    2.8897    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.6811    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368   -1.2286    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -1.9561    2.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104   -0.1056    2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643   -0.9420    1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 17 20  1  0
 17 18  1  6
 18 19  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8 16  1  0
 16 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11 10  1  0
 10  9  2  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  9 17  1  0
  3 24  1  0
  8 26  1  0
  9  8  1  0
 15 16  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 24 47  1  1
 25 48  1  0
 25 49  1  0
 26 50  1  1
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
  4 31  1  0
  4 32  1  0
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652304292206242D          

 26 30  0  0  1  0            999 V2000
    1.8969   -1.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -0.8766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2419   -0.4570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1531    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.6300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2451    1.3078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541    1.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374    1.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4427    0.4245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3663   -0.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262   -0.8166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507    1.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5754    1.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9687    0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373   -0.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329    0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6379    0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405   -1.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3327   -2.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738   -1.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958   -2.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 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
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(CO)[C@H]2C[C@@H]3N(CC[C@@]33C4=C(C=CC=C4)N=C13)C\C2=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-20-14-6-4-5-7-16(14)22-18(20)21(12-24,19(25)26-2)15(13)10-17(20)23/h3-7,15,17,24H,8-12H2,1-2H3/b13-3-/t15-,17-,20+,21-/m0/s1

> <INCHI_KEY>
DSOCELULQRKOMA-OQTQPSEISA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.30182514315652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,10S,11S,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,8-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.3651321859999994

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.754267571516625

> <JCHEM_PKA_STRONGEST_BASIC>
9.304437160748032

> <JCHEM_POLAR_SURFACE_AREA>
62.129999999999995

> <JCHEM_REFRACTIVITY>
101.61529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,10S,11S,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,8-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       3.541  -2.591   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.020  -2.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.050  -1.636   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.452  -0.853   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.286   0.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.233   1.176   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.458   2.441   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.781   3.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.057   2.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.693   0.792   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.551  -0.861   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.969  -1.524   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.064  -0.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.329   0.919   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.135   2.232   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.674   2.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.408   0.837   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.603  -0.476   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.118   2.040   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.555   0.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.057   0.099   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.516  -1.371   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.076  -2.829   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.621  -4.269   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.444  -2.581   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.419  -3.774   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11   23                                             
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   14                                             
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    7   20                                                       
CONECT   20   19    4   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    3   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   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

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

methyl (1R,10S,11S,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,8-tetraene-10-carboxylate

Traditional Name

methyl (1R,10S,11S,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,8-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(CO)[C@H]2C[C@@H]3N(CC[C@@]33C4=C(C=CC=C4)N=C13)C\C2=C\C

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-20-14-6-4-5-7-16(14)22-18(20)21(12-24,19(25)26-2)15(13)10-17(20)23/h3-7,15,17,24H,8-12H2,1-2H3/b13-3-/t15-,17-,20+,21-/m0/s1

InChI Key

DSOCELULQRKOMA-OQTQPSEISA-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
Alstonia Alstonia scholaris	Plant	KNApSAcK
Alstonia angustiloba	Plant	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Strempeliopsis strempelioides	Plant	KNApSAcK
Strychnos nux-vomica L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Stemmadenine-skeleton
3-alkylindole
Indole or derivatives
Indolizidine
Beta-hydroxy acid
Aralkylamine
N-alkylpyrrolidine
Hydroxy acid
Benzenoid
Piperidine
Pyrrolidine
Methyl ester
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Ketimine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Amine
Imine
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary alcohol
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	2.32	ALOGPS
logP	2.37	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	9.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	38.3 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

C00051792

Chemspider ID

29763444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Preakuammicine

METLIN ID

Not Available

PubChem Compound

71768191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tatsis EC, Carqueijeiro I, Duge de Bernonville T, Franke J, Dang TT, Oudin A, Lanoue A, Lafontaine F, Stavrinides AK, Clastre M, Courdavault V, O'Connor SE: A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate. Nat Commun. 2017 Aug 22;8(1):316. doi: 10.1038/s41467-017-00154-x. [PubMed:28827772 ]
Lim KH, Kam TS: Arboflorine, an unusual pentacyclic monoterpenoid indole alkaloid incorporating a third nitrogen atom. Org Lett. 2006 Apr 13;8(8):1733-5. doi: 10.1021/ol060348k. [PubMed:16597153 ]

Showing NP-Card for Preakuammicine (NP0083366)

MOL for NP0083366 (Preakuammicine)

3D MOL for NP0083366 (Preakuammicine)

3D SDF for NP0083366 (Preakuammicine)

3D-SDF for NP0083366 (Preakuammicine)

PDB for NP0083366 (Preakuammicine)

3D PDB for NP0083366 (Preakuammicine)

SMILES for NP0083366 (Preakuammicine)

INCHI for NP0083366 (Preakuammicine)

Structure for NP0083366 (Preakuammicine)

3D Structure for NP0083366 (Preakuammicine)