NP-MRD: Showing NP-Card for Voachalotine (NP0077355)

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Record Information

Version

2.0

Created at

2022-04-28 22:30:56 UTC

Updated at

2022-04-28 22:30:56 UTC

NP-MRD ID

NP0077355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Voachalotine

Description

Voachalotine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Voachalotine is found in Ervatamia officinalis , Ochrosia acuminata, Tabernaemontana heyneana and Voacanga chalotiana Pierre et Stapf.. Voachalotine was first documented in 2011 (PMID: 21892126). Based on a literature review a small amount of articles have been published on voachalotine (PMID: 35075954) (PMID: 33321518) (PMID: 30599414) (PMID: 23983637).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200302D          

 27 31  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -2.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905   -1.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -2.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  2  0  0  0  0
  5 17  1  0  0  0  0
  1 17  1  1  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.5287   -2.8660   -0.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487   -2.6641    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750   -1.7008    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126   -1.4255    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -0.6045    1.3109 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620   -1.2984    0.2128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2278   -1.1775   -1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606   -0.8129   -0.6567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6576    0.6109   -0.1394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4910    1.6069   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    1.4468   -2.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    0.8846    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637   -0.0008    0.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354    2.1363    0.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    2.3864    1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5616    0.7191    0.8677 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6157    1.5347    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.7544    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -0.5933    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1319   -0.9877   -0.1816 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -2.3702   -0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    0.0863   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881    0.2201   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8218    1.4990   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0536    2.6175   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150    2.4520    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424    1.1834    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162   -3.6511   -0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0605   -1.9992   -1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -3.3244   -1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882   -3.3323    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042   -0.9921    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -2.3866    2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -2.3400    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -2.1723   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716   -0.4173   -1.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3074   -0.9789   -1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5221    1.4975   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589    2.6088   -0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    0.9074   -1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7875    1.8195    2.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264    2.2950    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5975    3.4717    1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    1.1263    1.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    2.2861   -0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031    2.1451    1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -3.0563    0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -2.7326   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6658   -2.4186   -0.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553   -0.5913   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8714    1.6590   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089    3.6180   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    3.3221    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
  9 12  1  0
  9 10  1  6
 10 11  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
  8  9  1  0
 27 22  1  0
  5 16  1  0
 27 18  1  0
  5  6  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  6
  4 32  1  0
  4 33  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
M  END


  Mrv1652304292200302D          

 27 31  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -2.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905   -1.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -2.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4456   -3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  2  0  0  0  0
  5 17  1  0  0  0  0
  1 17  1  1  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(CO)[C@@H]2CC3=C([C@@H]4C[C@H]1\C(CN24)=C/C)N(C)C1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18-,19-,22+/m0/s1

> <INCHI_KEY>
IWEYXWIPVZEVPT-VQVRLUHXSA-N

> <FORMULA>
C22H26N2O3

> <MOLECULAR_WEIGHT>
366.461

> <EXACT_MASS>
366.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.66655053240132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,12S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.2620616713333326

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.808028891587885

> <JCHEM_PKA_STRONGEST_BASIC>
6.14218520841752

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
105.04669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,12S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-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  C   UNK     0      -1.452  -1.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.518  -3.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.023  -2.850   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.243  -1.321   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.408  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.086  -0.555   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.639  -1.992   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.573  -3.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.177  -1.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.574  -0.422   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.282   0.416   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.200   1.953   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.061  -0.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.151  -1.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.754  -2.599   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.266  -2.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.357  -0.555   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.323   0.125   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.299  -0.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.450   0.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.912   0.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.722  -3.976   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.156  -3.412   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.494  -5.499   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.698  -6.458   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.400  -4.552   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.989  -5.217   0.000  0.00  0.00           O+0
CONECT    1    2   17   19                                                  
CONECT    2    1    3   22   26                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9                                                       
CONECT   17    5    1                                                       
CONECT   18    4   19                                                       
CONECT   19   18    1   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    2   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Voachalotin	ChEBI

Chemical Formula

C₂₂H₂₆N₂O₃

Average Mass

366.4610 Da

Monoisotopic Mass

366.19434 Da

IUPAC Name

methyl (1S,12S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

Traditional Name

methyl (1S,12S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(CO)[C@@H]2CC3=C([C@@H]4C[C@H]1\C(CN24)=C/C)N(C)C1=CC=CC=C31

InChI Identifier

InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18-,19-,22+/m0/s1

InChI Key

IWEYXWIPVZEVPT-VQVRLUHXSA-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
Ervatamia officinalis	Plant	KNApSAcK
Ochrosia acuminata	Plant	KNApSAcK
Tabernaemontana heyneana	Plant	KNApSAcK
Voacanga chalotiana Pierre et Stapf.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Corynanthean skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Quinuclidine
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
N-methylpyrrole
Piperidine
Benzenoid
Substituted pyrrole
Pyrrole
Methyl ester
Heteroaromatic compound
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
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	2.62	ALOGPS
logP	2.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.81	ChemAxon
pKa (Strongest Basic)	6.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.05 m³·mol⁻¹	ChemAxon
Polarizability	40.67 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

C00040643

Chemspider ID

62991357

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444908

PDB ID

Not Available

ChEBI ID

141967

Good Scents ID

Not Available

References

General References

Reis FL, Adolpho L, Ruiz ALTG, Simionatto E, Dalcol II, Mostardeiro MA, Morel AF: In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res. 2022 Jan 25:1-5. doi: 10.1080/14786419.2021.2017928. [PubMed:35075954 ]
Musquiari B, Crevelin EJ, Bertoni BW, Franca SC, Pereira AMS, Castello ACD, Castillo-Ordonez WO, Giuliatti S, Lopes AA: Precursor-directed Biosynthesis in Tabernaemontana catharinensis as a New Avenue for Alzheimer's Disease-modifying Agents. Planta Med. 2021 Feb;87(1-02):136-147. doi: 10.1055/a-1315-2282. Epub 2020 Dec 15. [PubMed:33321518 ]
Rosales PF, Marinho FF, Gower A, Chiarello M, Canci B, Roesch-Ely M, Paula FR, Moura S: Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem. 2019 Apr;85:66-74. doi: 10.1016/j.bioorg.2018.12.016. Epub 2018 Dec 15. [PubMed:30599414 ]
Nicola C, Salvador M, Gower AE, Moura S, Echeverrigaray S: Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal. 2013 Jul 28;2013:519858. doi: 10.1155/2013/519858. eCollection 2013. [PubMed:23983637 ]
Goncalves MS, Vieira IJ, Oliveira RR, Braz-Filho R: Application of preparative high-speed counter-current chromatography for the separation of two alkaloids from the roots of Tabernaemontana catharinensis (Apocynaceae). Molecules. 2011 Sep 2;16(9):7480-7. doi: 10.3390/molecules16097480. [PubMed:21892126 ]

Showing NP-Card for Voachalotine (NP0077355)

MOL for NP0077355 (Voachalotine)

3D MOL for NP0077355 (Voachalotine)

3D SDF for NP0077355 (Voachalotine)

3D-SDF for NP0077355 (Voachalotine)

PDB for NP0077355 (Voachalotine)

3D PDB for NP0077355 (Voachalotine)

SMILES for NP0077355 (Voachalotine)

INCHI for NP0077355 (Voachalotine)

Structure for NP0077355 (Voachalotine)

3D Structure for NP0077355 (Voachalotine)