NP-MRD: Showing NP-Card for methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate (NP0154148)

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Record Information

Version

2.0

Created at

2022-09-02 10:55:08 UTC

Updated at

2022-09-02 10:55:08 UTC

NP-MRD ID

NP0154148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

Description

Vincamedine 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. methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate is found in Alstonia constricta, Alstonia macrophylla and Vinca major. Based on a literature review very few articles have been published on Vincamedine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212552D          

 30 35  0  0  1  0            999 V2000
   -0.4574   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032    0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7195    0.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -0.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316   -0.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    1.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238    2.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    3.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0788    1.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.5104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4921    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0451    0.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054    0.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7457   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -0.8415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1798   -1.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739   -0.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  1  0  0  0
  5 21  1  0  0  0  0
  9 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 19 30  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
    4.6811   -0.5503    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -1.4670   -0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7215   -1.5752   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9453   -2.4819   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -2.0539   -1.1714 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0092   -2.3026    0.1352 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0125   -1.8995    1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8837   -0.8053    0.5931 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0472    0.1425   -0.2331 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8813    1.2821   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574    1.4880   -1.8083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    2.1561    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996    3.2591   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -0.6104   -1.4563 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8360   -0.1847   -1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703   -0.1592   -0.1758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6591    0.2077   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025    1.4223    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6823    1.4815    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3808    0.3117    0.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7517   -0.9170    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.9796    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -2.0799    0.0371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034   -3.4188   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187   -1.5541    0.4348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2097    0.6175    0.4865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3351    1.9857    0.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780    2.9875    1.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    4.3921    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106    2.6520    2.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736    0.5150    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7892   -0.7485    0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955   -0.7765    1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849   -2.0575   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -3.5370   -1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2699   -2.2177   -2.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -3.4040    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5073   -1.5373    2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6022   -2.7946    1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370   -0.3117    1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788    4.1718    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738    3.0259    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    3.4477   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -0.4331   -2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.8554   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.9064   -2.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    2.3733   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1448    2.4528    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4472    0.3712    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3409   -1.8312    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1383   -3.7955   -1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6652   -4.1038    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8535   -3.5129   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038   -1.3586    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1013    0.4653    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9251    4.4332   -0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726    4.9059    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695    4.9623    1.3925 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 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 16 25  1  0
 25  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
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 26  9  1  0
  5  6  1  0
 17 22  1  0
  8  9  1  0
  5 14  1  0
 16 17  1  6
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  6
 15 45  1  0
 15 46  1  0
 26 55  1  1
 29 56  1  0
 29 57  1  0
 29 58  1  0
 25 54  1  1
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  1
  4 35  1  0
  4 36  1  0
  2 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 21 50  1  0
 20 49  1  0
 19 48  1  0
 18 47  1  0
M  END


  Mrv1652309022212552D          

 30 35  0  0  1  0            999 V2000
   -0.4574   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032    0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7195    0.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -0.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316   -0.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    1.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238    2.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    3.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0788    1.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.5104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4921    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0451    0.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054    0.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7457   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -0.8415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1798   -1.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739   -0.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  1  0  0  0
  5 21  1  0  0  0  0
  9 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 19 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12[C@@H]3C[C@]4(C1OC(C)=O)C(C1CC2\C(CN31)=C/C)N(C)C1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O4/c1-5-14-12-26-18-10-16(14)24(22(28)29-4)19(26)11-23(21(24)30-13(2)27)15-8-6-7-9-17(15)25(3)20(18)23/h5-9,16,18-21H,10-12H2,1-4H3/b14-5-/t16?,18?,19-,20?,21?,23+,24?/m0/s1

> <INCHI_KEY>
UBTOXVLVFCOIGT-QVCYJDDGSA-N

> <FORMULA>
C24H28N2O4

> <MOLECULAR_WEIGHT>
408.498

> <EXACT_MASS>
408.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.780576087340435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,13E,16S)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-triene-17-carboxylate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.2728203586666664

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.317083834712216

> <JCHEM_POLAR_SURFACE_AREA>
59.080000000000005

> <JCHEM_REFRACTIVITY>
112.2344

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,13E,16S)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-triene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.854  -2.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.990  -0.919   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.193   0.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.241   1.747   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.802   1.401   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.913  -0.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.058  -1.333   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.792   0.229   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.210   1.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.026   0.182   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.729  -0.127   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.792  -1.612   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.015  -2.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.837   2.358   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.458   3.994   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.171   5.607   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.724   6.132   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.350   6.599   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.937   0.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.881   2.391   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.432   2.819   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.519   0.694   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.551   1.837   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.057   1.515   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.530   0.049   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.498  -1.094   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.992  -0.771   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       5.637  -1.571   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       5.936  -3.168   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.431  -0.552   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   14   21                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   22   30                                             
CONECT   20   19   21                                                       
CONECT   21   20    5    9                                                  
CONECT   22   19   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    6   19                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈N₂O₄

Average Mass

408.4980 Da

Monoisotopic Mass

408.20491 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C12[C@@H]3C[C@]4(C1OC(C)=O)C(C1CC2\C(CN31)=C/C)N(C)C1=CC=CC=C41

InChI Identifier

InChI=1S/C24H28N2O4/c1-5-14-12-26-18-10-16(14)24(22(28)29-4)19(26)11-23(21(24)30-13(2)27)15-8-6-7-9-17(15)25(3)20(18)23/h5-9,16,18-21H,10-12H2,1-4H3/b14-5-/t16?,18?,19-,20?,21?,23+,24?/m0/s1

InChI Key

UBTOXVLVFCOIGT-QVCYJDDGSA-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
Alstonia constricta	LOTUS Database	35616633
Alstonia macrophylla	LOTUS Database	35616633
Vinca major	LOTUS Database	35616633

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
Pyridoindole
Beta-carboline
Quinolizidine
Piperidinecarboxylic acid
Indole or derivatives
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Quinuclidine
Aralkylamine
Azepane
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Methyl ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024296

Chemspider ID

10143016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11969611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate (NP0154148)

MOL for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

3D MOL for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

3D SDF for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

3D-SDF for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

PDB for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

3D PDB for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

SMILES for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

INCHI for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

Structure for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)

3D Structure for NP0154148 (methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate)