NP-MRD: Showing NP-Card for methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate (NP0186647)

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Record Information

Version

2.0

Created at

2022-09-04 02:34:41 UTC

Updated at

2022-09-04 02:34:41 UTC

NP-MRD ID

NP0186647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Description

Dregamine belongs to the class of organic compounds known as vobasan alkaloids. These are alkaloids containing the vobasan skeleton. Dregamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate is found in Tabernaemontana calcarea. methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate was first documented in 2019 (PMID: 30987224). Based on a literature review a small amount of articles have been published on dregamine (PMID: 33189435) (PMID: 30048730) (PMID: 34577562) (PMID: 33899955).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204342D          

 26 29  0  0  1  0            999 V2000
   -1.5116    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749    0.1425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0276   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.1439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -1.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151   -0.7825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3878   -0.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    0.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192    1.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601    0.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1571   -1.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848   -0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099    1.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4318    2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4549    1.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515    0.5620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2296   -0.0875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7865    0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266   -0.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333    1.5726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    1.7773    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  0  0  0  0
  5  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 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
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -4.5478   -2.6389    0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -2.1980   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -0.9142    0.2898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1594   -1.0363    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834   -0.6671    1.4813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124   -0.7662    2.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    0.7213    1.0138 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7742    1.1507    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    0.3518    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.5840   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209   -0.9549   -1.3801 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427   -0.2736   -0.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297   -0.2486   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7065    0.5761    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    1.3962    1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827    1.3856    1.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049    0.5463    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -1.1969   -1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118   -1.5085   -2.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0229   -1.4960   -1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.4180   -0.7964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4399    0.8771   -0.2367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8635    1.7670   -1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    1.3081   -2.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501    3.1014   -1.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    3.9150   -2.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -3.7346    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422   -2.1912    0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178   -2.1864    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8710   -3.0246   -0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380   -2.0692   -1.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7180   -0.1332    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -0.5177    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822   -2.1257    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -1.3435    2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   -1.3444    3.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    0.2080    3.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    1.3095    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350    1.1471    1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934    2.2084    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9275   -1.6390   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377   -0.8864   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7913    0.6210    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165    2.0531    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1425    2.0253    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -2.2571   -0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -2.1134   -1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -0.1635   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939    1.4219    0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    4.9583   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008    3.6461   -3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973    3.9354   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 21  3  1  0
 22  7  1  0
 17  9  1  0
 17 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  1
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  1
  8 39  1  0
  8 40  1  0
 11 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  1
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END


  Mrv1652309042204342D          

 26 29  0  0  1  0            999 V2000
   -1.5116    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749    0.1425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0276   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098   -1.1439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -1.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151   -0.7825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3878   -0.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    0.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192    1.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601    0.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1571   -1.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848   -0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099    1.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4318    2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4549    1.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515    0.5620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2296   -0.0875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7865    0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266   -0.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333    1.5726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    1.7773    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  0  0  0  0
  5  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 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
M  END
> <DATABASE_ID>
NP0186647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN(C)[C@H]2CC3=C(NC4=CC=CC=C34)C(=O)C[C@@H]1[C@@H]2C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14-,17-,19-/m0/s1

> <INCHI_KEY>
FFVRRQMGGGTQRH-YWKPPDPDSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.84682764273424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,14S,15R,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraene-18-carboxylate

> <JCHEM_LOGP>
2.658626856333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.464581735602962

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.335590731920991

> <JCHEM_PKA_STRONGEST_BASIC>
7.6545488673946105

> <JCHEM_POLAR_SURFACE_AREA>
62.4

> <JCHEM_REFRACTIVITY>
100.63359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,14S,15R,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.822   0.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.291   1.045   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.140   0.266   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.051  -1.321   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.325  -2.135   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.213  -3.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.828  -1.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.457  -1.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.579  -0.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.503   1.399   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.943   1.947   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.908   0.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.446   0.661   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.140  -0.713   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.297  -2.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.760  -1.916   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.065  -0.542   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.312   2.428   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.539   4.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.716   2.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.590   1.049   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.295  -0.163   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.335   1.125   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.343  -0.146   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.422   2.936   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.714   3.318   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21    7   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(-)-Dregamine	ChEBI
20-Epitabernemontanine	ChEBI

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (1S,14S,15R,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Traditional Name

methyl (1S,14S,15R,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraene-18-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN(C)[C@H]2CC3=C(NC4=CC=CC=C34)C(=O)C[C@@H]1[C@@H]2C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14-,17-,19-/m0/s1

InChI Key

FFVRRQMGGGTQRH-YWKPPDPDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Tabernaemontana calcarea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vobasan alkaloids. These are alkaloids containing the vobasan skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Vobasan alkaloids

Sub Class

Not Available

Direct Parent

Vobasan alkaloids

Alternative Parents

Substituents

Vobasan skeleton
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Pyrrole
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	2.66	ChemAxon
pKa (Strongest Acidic)	12.34	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.63 m³·mol⁻¹	ChemAxon
Polarizability	38.85 Å³	ChemAxon
Number of Rings	4	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

C00025859

Chemspider ID

19974575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dregamine

METLIN ID

Not Available

PubChem Compound

12309361

PDB ID

Not Available

ChEBI ID

141897

Good Scents ID

Not Available

References

General References

Zhou J, Du SY, Dong HJ, Fang L, Feng JH: Preparative Separation of Monoterpenoid Indole Alkaloid Epimers from Ervatamia yunnanensis Tsiang by pH-Zone-Refining Counter-Current Chromatography Combined with Preparative High-Performance Liquid Chromatography. Molecules. 2019 Apr 3;24(7). pii: molecules24071316. doi: 10.3390/molecules24071316. [PubMed:30987224 ]
Cardoso DSP, Kincses A, Nove M, Spengler G, Mulhovo S, Aires-de-Sousa J, Dos Santos DJVA, Ferreira MU: Alkylated monoterpene indole alkaloid derivatives as potent P-glycoprotein inhibitors in resistant cancer cells. Eur J Med Chem. 2021 Jan 15;210:112985. doi: 10.1016/j.ejmech.2020.112985. Epub 2020 Nov 4. [PubMed:33189435 ]
Bapela MJ, Heyman H, Senejoux F, Meyer JJM: (1)H NMR-based metabolomics of antimalarial plant species traditionally used by Vha-Venda people in Limpopo Province, South Africa and isolation of antiplasmodial compounds. J Ethnopharmacol. 2019 Jan 10;228:148-155. doi: 10.1016/j.jep.2018.07.022. Epub 2018 Jul 23. [PubMed:30048730 ]
Cardoso DSP, Szemeredi N, Spengler G, Mulhovo S, Dos Santos DJVA, Ferreira MU: Exploring the Monoterpene Indole Alkaloid Scaffold for Reversing P-Glycoprotein-Mediated Multidrug Resistance in Cancer. Pharmaceuticals (Basel). 2021 Aug 28;14(9):862. doi: 10.3390/ph14090862. [PubMed:34577562 ]
Raimundo L, Paterna A, Calheiros J, Ribeiro J, Cardoso DSP, Piga I, Neto SJ, Hegan D, Glazer PM, Indraccolo S, Mulhovo S, Costa JL, Ferreira MU, Saraiva L: BBIT20 inhibits homologous DNA repair with disruption of the BRCA1-BARD1 interaction in breast and ovarian cancer. Br J Pharmacol. 2021 Sep;178(18):3627-3647. doi: 10.1111/bph.15506. Epub 2021 Jun 11. [PubMed:33899955 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate (NP0186647)

MOL for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D MOL for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D SDF for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D-SDF for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

PDB for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D PDB for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

SMILES for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

INCHI for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

Structure for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D Structure for NP0186647 (methyl (1s,14s,15r,18s)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)