NP-MRD: Showing NP-Card for (+)-Dehydrovoachalotine (NP0068674)

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Record Information

Version

2.0

Created at

2022-04-28 13:56:20 UTC

Updated at

2022-04-28 13:56:21 UTC

NP-MRD ID

NP0068674

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dehydrovoachalotine

Description

Dehydrovoachalotine 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. (+)-Dehydrovoachalotine is found in Alstonia undulata, Voacanda chalotiana and Voacanga chalotiana Pierre et Stapf.. Based on a literature review very few articles have been published on Dehydrovoachalotine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215562D          

 27 32  0  0  1  0            999 V2000
    4.1394   -0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    0.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863    0.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -0.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392   -0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996    1.0532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    1.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    0.7438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8090   -0.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -0.7213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3441   -0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9446   -1.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -1.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2212   -0.8271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799   -0.7566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -1.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    0.1178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0829    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814    0.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 27  1  0  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
   -4.0726    2.8875   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3433    2.2087   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998    1.4507   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201    1.1816   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    0.5261   -1.2899 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602    1.3199   -0.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2690    1.4858    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373    0.8154    0.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4654   -0.6450    0.5647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7831   -1.3079    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7942   -0.6734    0.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8997   -2.6206    0.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839   -3.2571    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -1.4144    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -2.2975    0.7025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963   -1.5680   -0.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6869   -0.7380   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    0.6292   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092    1.0798    0.0350 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2555    2.4841    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.0470    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1181    0.0166    0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237   -1.2179    0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -2.3851    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -2.2945    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901   -1.0886    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7337   -0.7694   -0.7376 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8093    2.4359   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1552    2.7938   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    3.9532   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    2.3819    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229    0.4837   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    2.0895   -2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5079    2.3171   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4429    2.5846    1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566    1.1353    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    0.9739    1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7906   -2.8803   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7321   -3.0347    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863   -4.3491    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920   -0.8463    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -2.0342    2.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651   -2.2734   -1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340    3.0730    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    2.8963   -0.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2130    2.6016    0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    0.9470    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -1.2308    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4891   -3.3702    0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0605   -3.1998   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3751   -1.3028   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
  9 10  1  6
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 27  1  0
 27  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  3  8  1  0
  8  7  1  0
  7  6  1  0
  6 18  1  0
 18 17  2  0
 17 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 19  1  0
 19 20  1  0
 27  9  1  0
  6  5  1  0
 19 18  1  0
  8  9  1  0
 21 26  1  0
 17 16  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  6
 27 51  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
  8 37  1  1
  7 35  1  0
  7 36  1  0
  6 34  1  6
 25 50  1  0
 24 49  1  0
 23 48  1  0
 22 47  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv1652304282215562D          

 27 32  0  0  1  0            999 V2000
    4.1394   -0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    0.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863    0.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -0.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392   -0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996    1.0532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    1.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    0.7438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8090   -0.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -0.7213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3441   -0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9446   -1.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -1.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2212   -0.8271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8799   -0.7566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -1.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    0.1178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0829    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814    0.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 12 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068674

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12CO[C@H]3[C@@H]1N1CC(=CC)[C@@H]2C[C@H]1C1=C3C2=CC=CC=C2N1C

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O3/c1-4-12-10-24-16-9-14(12)22(21(25)26-3)11-27-19(20(22)24)17-13-7-5-6-8-15(13)23(2)18(16)17/h4-8,14,16,19-20H,9-11H2,1-3H3/b12-4-/t14-,16?,19+,20-,22+/m0/s1

> <INCHI_KEY>
NYKBMPZVJCLGAM-PRPXRCPYSA-N

> <FORMULA>
C22H24N2O3

> <MOLECULAR_WEIGHT>
364.445

> <EXACT_MASS>
364.178692641

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.02901044600273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,4S,5E,8R,9R,12R)-5-ethylidene-20-methyl-11-oxa-7,20-diazahexacyclo[11.7.0.0^{2,7}.0^{4,9}.0^{8,12}.0^{14,19}]icosa-1(13),14,16,18-tetraene-9-carboxylate

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.5047690966666654

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.417166791841888

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
102.7441

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4S,5E,8R,9R,12R)-5-ethylidene-20-methyl-11-oxa-7,20-diazahexacyclo[11.7.0.0^{2,7}.0^{4,9}.0^{8,12}.0^{14,19}]icosa-1(13),14,16,18-tetraene-9-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       7.727  -1.091   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.143   0.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.066   1.494   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.574   1.112   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.159  -0.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.235  -1.472   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.620  -0.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.085   1.011   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.293   1.966   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.671   3.536   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.533   1.388   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.510  -0.312   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.076  -1.346   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.509  -1.758   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.763  -3.201   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.133  -3.093   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.413  -1.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.029  -2.146   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.509  -1.412   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.808  -3.528   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.348  -3.544   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.853   0.220   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.155   1.659   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.085   0.549   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.399   1.967   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.079   3.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.010  -0.633   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   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   23                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18   22                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22   11                                                       
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   12                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄N₂O₃

Average Mass

364.4450 Da

Monoisotopic Mass

364.17869 Da

IUPAC Name

methyl (2S,4S,5E,8R,9R,12R)-5-ethylidene-20-methyl-11-oxa-7,20-diazahexacyclo[11.7.0.0^{2,7}.0^{4,9}.0^{8,12}.0^{14,19}]icosa-1(13),14,16,18-tetraene-9-carboxylate

Traditional Name

methyl (2S,4S,5E,8R,9R,12R)-5-ethylidene-20-methyl-11-oxa-7,20-diazahexacyclo[11.7.0.0^{2,7}.0^{4,9}.0^{8,12}.0^{14,19}]icosa-1(13),14,16,18-tetraene-9-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12CO[C@H]3[C@@H]1N1CC(=CC)[C@@H]2C[C@H]1C1=C3C2=CC=CC=C2N1C

InChI Identifier

InChI=1S/C22H24N2O3/c1-4-12-10-24-16-9-14(12)22(21(25)26-3)11-27-19(20(22)24)17-13-7-5-6-8-15(13)23(2)18(16)17/h4-8,14,16,19-20H,9-11H2,1-3H3/b12-4-/t14-,16?,19+,20-,22+/m0/s1

InChI Key

NYKBMPZVJCLGAM-PRPXRCPYSA-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 undulata	Plant	KNApSAcK
Voacanda chalotiana	-	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
Aralkylamine
N-methylpyrrole
Piperidine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Oxolane
Pyrrole
Methyl ester
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic nitrogen compound
Organonitrogen 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	3.27	ALOGPS
logP	2.5	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	5.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.74 m³·mol⁻¹	ChemAxon
Polarizability	40.03 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

C00026687

Chemspider ID

68024175

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101289798

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Dehydrovoachalotine (NP0068674)

MOL for NP0068674 ((+)-Dehydrovoachalotine)

3D MOL for NP0068674 ((+)-Dehydrovoachalotine)

3D SDF for NP0068674 ((+)-Dehydrovoachalotine)

3D-SDF for NP0068674 ((+)-Dehydrovoachalotine)

PDB for NP0068674 ((+)-Dehydrovoachalotine)

3D PDB for NP0068674 ((+)-Dehydrovoachalotine)

SMILES for NP0068674 ((+)-Dehydrovoachalotine)

INCHI for NP0068674 ((+)-Dehydrovoachalotine)

Structure for NP0068674 ((+)-Dehydrovoachalotine)

3D Structure for NP0068674 ((+)-Dehydrovoachalotine)