NP-MRD: Showing NP-Card for Deoxyakuammine (NP0067448)

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Record Information

Version

2.0

Created at

2022-04-28 12:18:13 UTC

Updated at

2022-04-28 12:18:13 UTC

NP-MRD ID

NP0067448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxyakuammine

Description

Methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0¹,⁹.0³,⁸.0⁹,¹⁶.0¹²,¹⁹]Icosa-3,5,7-triene-16-carboxylate belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. Deoxyakuammine is found in Alstonia scholaris, Alstonia scholaris R.Br. and Alstonia yunnanensis. Based on a literature review very few articles have been published on methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0¹,⁹.0³,⁸.0⁹,¹⁶.0¹²,¹⁹]Icosa-3,5,7-triene-16-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214182D          

 27 32  0  0  1  0            999 V2000
   -2.5962    0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -0.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0491   -1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2870   -0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -0.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0255   -0.7244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5423   -1.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1370   -1.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.4307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -0.8481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2538   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    0.2875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8344    0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    0.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419   -0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -0.0179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9318    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556   -0.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218    0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    1.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    1.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0878    1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621    0.7255    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  4  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 12 19  1  0  0  0  0
 15 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 20 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
    4.1596   -0.9783   -1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -0.6451   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168   -1.1802   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6098   -2.2234   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899   -2.2993   -0.8690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3589   -1.4279   -1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -0.0143   -1.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893    0.1895    0.0307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6684    1.1778    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616    2.5584    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322    3.2644    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180    2.5879    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0261    1.2075    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    0.4724    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -0.9442    0.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -1.8763   -0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2437   -1.0340    0.6823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2552   -0.7153    2.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985    0.2318    2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    0.3451    0.9979 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2428    1.6198    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651    2.4352    1.9245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116    1.9811   -0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6284    3.1667   -0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622   -0.8176    1.1047 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7093   -2.1195    1.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -2.1963    0.4002 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0372   -0.1531   -2.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9113   -1.9768   -2.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278   -1.0145   -1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8113    0.1055    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -3.2081   -0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749   -1.9378   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3152   -1.5543   -2.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578   -1.6877   -2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606    0.6201   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386    0.3061   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7404    3.1174    0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783    4.3562    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9268    3.1618    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9689    0.7009    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5135   -1.8144    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687   -2.9034   -0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -1.7554   -1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222    1.2425    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.0301    3.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760    3.1794    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177    3.2124   -1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0031    4.0491   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125   -0.6399    1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431   -2.0589    2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104   -2.9503    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9764   -3.1325    0.6745 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  6
 20 19  1  0
 19 18  1  0
 17 18  1  1
 17 27  1  0
 27 26  1  0
 26 25  1  0
 25  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
  3  2  2  0
  2  1  1  0
 25 20  1  0
 14  9  1  0
  8 20  1  0
  8 17  1  0
 15 17  1  0
  5 27  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 19 45  1  0
 19 46  1  0
 27 53  1  1
 26 51  1  0
 26 52  1  0
 25 50  1  1
  4 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652304282214182D          

 27 32  0  0  1  0            999 V2000
   -2.5962    0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -0.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0491   -1.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2870   -0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -0.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0255   -0.7244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5423   -1.3230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1370   -1.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -2.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.4307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -0.8481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2538   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    0.2875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8344    0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    0.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0419   -0.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -0.0179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9318    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556   -0.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218    0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    1.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    1.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0878    1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621    0.7255    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  4  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 12 19  1  0  0  0  0
 15 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 20 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12CO[C@]34[C@@H]5C[C@H]1\C(CN5CC[C@]23C1=CC=CC=C1N4C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-21-15-7-5-6-8-17(15)23(2)22(21)18(24)11-16(14)20(21,13-27-22)19(25)26-3/h4-8,16,18H,9-13H2,1-3H3/b14-4+/t16-,18-,20-,21-,22+/m0/s1

> <INCHI_KEY>
HAGBWVNSVWLTKY-BYNNPYNYSA-N

> <FORMULA>
C22H26N2O3

> <MOLECULAR_WEIGHT>
366.461

> <EXACT_MASS>
366.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.48726689112056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0^{1,9}.0^{3,8}.0^{9,16}.0^{12,19}]icosa-3,5,7-triene-16-carboxylate

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.8557052823333327

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.077168192633142

> <JCHEM_POLAR_SURFACE_AREA>
42.010000000000005

> <JCHEM_REFRACTIVITY>
103.66869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0^{1,9}.0^{3,8}.0^{9,16}.0^{12,19}]icosa-3,5,7-triene-16-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      -4.846   0.068   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.047  -1.459   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.825  -2.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.402  -1.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.202  -0.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.424   0.657   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.870  -0.117   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.048  -1.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.012  -2.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.256  -3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.352  -3.909   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.504  -2.671   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.659  -1.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.340  -0.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.470   0.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.424   0.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.510   1.195   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.999   0.800   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.812  -1.602   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.218  -0.033   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.739   0.074   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.784  -1.486   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.414   1.494   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.811   2.427   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.835   2.088   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.031   3.616   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.423   1.354   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   27                                                  
CONECT    8    7    9   13   22                                             
CONECT    9    8    4   10   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   12                                                       
CONECT   20   15    9   21   23                                             
CONECT   21   20   22                                                       
CONECT   22   21    8                                                       
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0,.0,.0,.0,]icosa-3,5,7-triene-16-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₆N₂O₃

Average Mass

366.4610 Da

Monoisotopic Mass

366.19434 Da

IUPAC Name

methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0^{1,9}.0^{3,8}.0^{9,16}.0^{12,19}]icosa-3,5,7-triene-16-carboxylate

Traditional Name

methyl (1S,9S,14Z,15S,16R,19S)-14-ethylidene-2-methyl-18-oxa-2,12-diazahexacyclo[13.3.2.0^{1,9}.0^{3,8}.0^{9,16}.0^{12,19}]icosa-3,5,7-triene-16-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12CO[C@]34[C@@H]5C[C@H]1\C(CN5CC[C@]23C1=CC=CC=C1N4C)=C\C

InChI Identifier

InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-21-15-7-5-6-8-17(15)23(2)22(21)18(24)11-16(14)20(21,13-27-22)19(25)26-3/h4-8,16,18H,9-13H2,1-3H3/b14-4+/t16-,18-,20-,21-,22+/m0/s1

InChI Key

HAGBWVNSVWLTKY-BYNNPYNYSA-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 scholaris	LOTUS Database	35616633
Alstonia scholaris R.Br.	Plant	KNApSAcK
Alstonia yunnanensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Carbazole
Pyridoindole
Quinolizidine
Indole or derivatives
Dialkylarylamine
Oxepane
Aralkylamine
Piperidine
Benzenoid
Methyl ester
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen 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	3.05	ALOGPS
logP	2.86	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.01 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.67 m³·mol⁻¹	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162996738

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Deoxyakuammine (NP0067448)

MOL for NP0067448 (Deoxyakuammine)

3D MOL for NP0067448 (Deoxyakuammine)

3D SDF for NP0067448 (Deoxyakuammine)

3D-SDF for NP0067448 (Deoxyakuammine)

PDB for NP0067448 (Deoxyakuammine)

3D PDB for NP0067448 (Deoxyakuammine)

SMILES for NP0067448 (Deoxyakuammine)

INCHI for NP0067448 (Deoxyakuammine)

Structure for NP0067448 (Deoxyakuammine)

3D Structure for NP0067448 (Deoxyakuammine)