NP-MRD: Showing NP-Card for methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate (NP0229566)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 09:41:22 UTC

Updated at

2022-09-06 09:41:22 UTC

NP-MRD ID

NP0229566

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Description

Methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]Octadeca-3(11),4,6,8-tetraene-18-carboxylate belongs to the class of organic compounds known as vobasan alkaloids. These are alkaloids containing the vobasan skeleton. methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate is found in Hunteria zeylanica. Methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]Octadeca-3(11),4,6,8-tetraene-18-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508552D          

 39 44  0  0  0  0            999 V2000
    8.1926   -0.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6827   -0.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5533   -1.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8385   -2.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2740   -2.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3537   -1.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2465   -1.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0242   -1.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1296   -1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6607   -0.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8485   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7348    0.6253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4768    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7053    1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5061    1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0784    1.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8498    0.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0491    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1609   -0.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0677   -1.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5549   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7948   -3.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3577   -3.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5139   -4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5961   -3.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1880   -2.7696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8983   -3.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4464   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4464    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0175    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328    0.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111    1.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935    1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    2.5843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -0.5385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0175   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -0.6960    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  4  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  2  0  0  0  0
 28 39  1  0  0  0  0
M  END

     RDKit          3D

 77 82  0  0  0  0  0  0  0  0999 V2000
   -2.3397   -3.7229    2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -2.8967    1.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -1.7576    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -1.1712    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0948   -0.2691    0.6421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735    0.5745    1.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858    0.3989   -0.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5922    1.5427    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439    1.9548   -0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    1.3412   -0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    2.3297   -1.3656 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882    3.5177   -1.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5525    4.8063   -1.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    5.9010   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    5.7021   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    4.4337   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540    3.3104   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245    0.0265   -1.1554 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8166    0.0695   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.2179   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090    0.2668   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    0.1636    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5572    0.1802    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9421    0.3216    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4291   -0.9767    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4297   -2.0533    1.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404    0.0372    2.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.0590    2.5496 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976    0.0130    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -0.0343    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.1926   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141   -0.9018   -0.1063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6066   -0.6792   -1.0993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3056   -0.5646   -2.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761   -0.4196   -3.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -1.9250   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -1.7977   -0.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -3.1683   -1.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371   -4.2874   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813   -4.4352    1.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5826   -4.3035    2.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992   -3.0761    3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -3.2667    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0690   -1.9820    1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018   -0.6221    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5705    0.9481    2.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8827   -0.0305    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3697    1.3821    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839    0.7129   -1.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407    1.4717    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349    2.4032    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    2.2293   -1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5380    4.9436   -1.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651    6.8864   -1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725    6.5433   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996    4.3606    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512   -0.0757   -2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254    0.3013   -2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707    0.3841   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6309    0.5709    1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0159    1.0958   -0.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8014   -1.3023   -0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4517   -0.8235   -0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493   -2.3129    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -1.6925    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897    0.0074    3.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426   -0.1745    3.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -0.1518    1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -1.9863   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -1.6536    0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930   -0.0158    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574    0.2649   -2.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -1.5661   -2.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026   -0.4739   -4.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6859   -4.9130   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6991   -4.8853   -2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9159   -3.9944   -1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 36  1  0
 36 37  2  0
 33 36  1  6
 33 34  1  0
 34 35  1  0
 33  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 31  1  0
 31 32  1  0
 32  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  2  2  0
  2  1  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 32 33  1  0
 30 19  1  0
  5  7  1  0
 29 22  1  0
 17  9  1  0
 17 12  1  0
 39 75  1  0
 39 76  1  0
 39 77  1  0
 34 72  1  0
 34 73  1  0
 35 74  1  0
  7 49  1  6
  8 50  1  0
  8 51  1  0
 11 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  6
 31 69  1  0
 31 70  1  0
 32 71  1  1
  4 44  1  0
  4 45  1  0
  6 46  1  0
  6 47  1  0
  6 48  1  0
  2 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 20 58  1  0
 21 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
 28 67  1  0
 30 68  1  0
M  END


  Mrv1533004241508552D          

 39 44  0  0  0  0            999 V2000
    8.1926   -0.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6827   -0.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5533   -1.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8385   -2.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2740   -2.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3537   -1.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2465   -1.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0242   -1.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1296   -1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6607   -0.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8485   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7348    0.6253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4768    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7053    1.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5061    1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0784    1.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8498    0.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0491    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1609   -0.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0677   -1.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5549   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7948   -3.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3577   -3.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5139   -4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5961   -3.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1880   -2.7696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8983   -3.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4464   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4464    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0175    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328    0.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111    1.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935    1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    2.5843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -0.5385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0175   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7319   -0.6960    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  4  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  2  0  0  0  0
 28 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229566

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(CO)C2CC3=C(NC4=CC=CC=C34)C(CC1C(CN2C)=CC)C1=CC=C2C(CCN)=CNC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H38N4O3/c1-4-19-17-36(2)29-15-25-23-7-5-6-8-27(23)35-30(25)24(14-26(19)32(29,18-37)31(38)39-3)20-9-10-22-21(11-12-33)16-34-28(22)13-20/h4-10,13,16,24,26,29,34-35,37H,11-12,14-15,17-18,33H2,1-3H3

> <INCHI_KEY>
QKLBOXIFIITUPD-UHFFFAOYSA-N

> <FORMULA>
C32H38N4O3

> <MOLECULAR_WEIGHT>
526.681

> <EXACT_MASS>
526.2943911

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.26717462351104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
3.6066805769999997

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
15.704617682329015

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.749424405234251

> <JCHEM_PKA_STRONGEST_BASIC>
9.73839196096795

> <JCHEM_POLAR_SURFACE_AREA>
107.37

> <JCHEM_REFRACTIVITY>
155.93129999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      15.293  -0.166   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.208  -1.628   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.966  -3.202   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.632  -4.361   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      17.311  -3.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.327  -3.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      20.993  -3.289   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.712  -3.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.909  -1.964   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.033  -0.628   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.517  -0.358   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      16.305   1.167   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      17.690   1.840   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.117   3.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.611   3.691   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.680   2.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.253   1.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.758   0.731   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.234  -1.299   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.060  -2.887   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.969  -4.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.417  -5.794   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.601  -7.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.893  -8.791   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.913  -6.297   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      19.018  -5.170   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      20.344  -6.086   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.900  -0.529   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.900   1.011   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.566   1.781   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.233   1.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.768   1.487   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.167   2.981   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.641   3.347   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       7.204   4.824   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       8.863   0.241   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       9.768  -1.005   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0      11.233  -0.529   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.566  -1.299   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8   21                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13                                                  
CONECT   19   11   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25    8   27                                                  
CONECT   27   26                                                            
CONECT   28   19   29   39                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   32   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   31   39                                                  
CONECT   39   38   28                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0,.0,]octadeca-3(11),4,6,8-tetraene-18-carboxylic acid	Generator
Methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₈N₄O₃

Average Mass

526.6810 Da

Monoisotopic Mass

526.29439 Da

IUPAC Name

methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Traditional Name

methyl 12-[3-(2-aminoethyl)-1H-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(CO)C2CC3=C(NC4=CC=CC=C34)C(CC1C(CN2C)=CC)C1=CC=C2C(CCN)=CNC2=C1

InChI Identifier

InChI=1S/C32H38N4O3/c1-4-19-17-36(2)29-15-25-23-7-5-6-8-27(23)35-30(25)24(14-26(19)32(29,18-37)31(38)39-3)20-9-10-22-21(11-12-33)16-34-28(22)13-20/h4-10,13,16,24,26,29,34-35,37H,11-12,14-15,17-18,33H2,1-3H3

InChI Key

QKLBOXIFIITUPD-UHFFFAOYSA-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
Hunteria zeylanica	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
Tryptamine
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
2-arylethylamine
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Piperidine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
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
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic nitrogen compound
Primary alcohol
Primary amine
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	3.97	ALOGPS
logP	3.61	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.93 m³·mol⁻¹	ChemAxon
Polarizability	60.27 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate (NP0229566)

MOL for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D MOL for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D SDF for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D-SDF for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

PDB for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D PDB for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

SMILES for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

INCHI for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

Structure for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)

3D Structure for NP0229566 (methyl 12-[3-(2-aminoethyl)-1h-indol-6-yl]-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate)