NP-MRD: Showing NP-Card for methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate (NP0292000)

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Record Information

Version

2.0

Created at

2022-09-09 23:19:07 UTC

Updated at

2022-09-09 23:19:07 UTC

NP-MRD ID

NP0292000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Description

Methyl 14-[4-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-5-ethyl-12-hydroxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11(16),12,14-tetraen-13-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8-tetraene-19-carboxylate belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. Methyl 14-[4-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-5-ethyl-12-hydroxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),11(16),12,14-tetraen-13-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8-tetraene-19-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161504542D          

 54 62  0  0  0  0            999 V2000
    5.9508   -0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3218   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1454   -0.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981   -0.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4217   -0.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8744   -1.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6980   -1.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0690   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6164   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1325    0.6263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9041    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6373    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3314    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2922   -0.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9863   -1.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7195   -0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7587    0.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4920    0.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1861    0.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9193    0.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1468   -0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4136   -1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3744   -1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6411   -2.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9470   -1.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2138   -2.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1746   -3.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8686   -3.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6019   -3.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1881   -3.6783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8171   -4.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1164   -5.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6003   -5.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7849   -5.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4855   -4.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0016   -4.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8409   -1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8017   -1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5742   -0.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2682   -1.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589   -0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5197   -1.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8649   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7927   -0.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3401    0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5164    0.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0637    1.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347    2.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9821    2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3531    3.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2401    1.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8691    0.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7874    1.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1584    2.6473    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  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
 21 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
  8 43  1  0  0  0  0
 11 43  1  0  0  0  0
  9 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  4  0  0  0
 49 50  1  0  0  0  0
 47 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

     RDKit          3D

106114  0  0  0  0  0  0  0  0999 V2000
    7.7309   -3.0185    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7437   -1.9076   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5256   -1.0767   -0.9081 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2940   -1.8586   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0738   -1.1841   -1.1406 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -1.6029   -2.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -0.6407   -2.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374    0.0258   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071    0.4702   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    1.0247    0.8448 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713    0.9912    0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618    1.4760    1.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    1.3091    1.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.7049    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.4841   -0.0395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1265    1.6866    0.1426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4864    2.9821    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321    3.5868    1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4798    3.8679    1.5543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5535    4.9329    0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2650    2.7200    0.9673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9948    3.2052   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2425    3.1615   -0.3862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2866    3.7090   -1.3462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8553    4.1788   -2.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5074    1.4858    0.6880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5402    0.5227    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -0.7478    1.4835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6691   -1.7201    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8649   -1.8165    0.1746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0186   -3.0525   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0233   -3.6877   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9035   -4.9744   -1.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7310   -5.6959   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -5.0793   -0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8530   -3.7898   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328   -2.9348    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414   -3.0120    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -1.7757    0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871   -0.5652    0.9177 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387    0.2164   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405   -0.3969   -1.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118    0.3692   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0466    0.2102   -0.9021 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0968    0.7176    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475   -0.0474    0.1340 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5371    0.7380    0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7482    1.9361    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8689    2.6856    0.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.7584   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4691    0.2866    1.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4656    1.0213    1.8598 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3938   -0.8995    2.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3163   -1.2874    3.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0318   -2.9271    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6046   -4.0118   -0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7647   -3.1000    0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6653   -1.2798   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9159   -2.3644   -1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384   -0.4294   -1.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2624   -2.6782   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063   -2.4672   -2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -2.6178   -2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.6148   -3.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1213   -1.1719   -2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    0.1783   -3.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205    1.4330    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    1.9529    2.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    1.6488    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3539    0.0042   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3998    1.9194   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191    3.8080   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    3.0784    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5294    4.5972    1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901    3.0781    2.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8922    4.2100    2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726    5.6937    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0781    2.5042    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3502    5.1808   -2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5629    3.4588   -2.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0082    4.2736   -3.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1157    0.9497   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6258    0.2432    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    0.9047    2.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6538   -1.2446    2.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5788   -1.0642    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9310   -3.1423   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7141   -5.4499   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6377   -6.6948   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8070   -5.6189   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -2.9747    2.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1387   -3.8851    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685   -1.8272    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180   -1.9480   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0028   -0.5833   -2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
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 50101  1  0
 50102  1  0
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 54104  1  0
 54105  1  0
 54106  1  0
M  END


  Mrv1533004161504542D          

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    8.3401    0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2401    1.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1584    2.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
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 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 25  1  0  0  0  0
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 26 27  1  0  0  0  0
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 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
 21 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
  8 43  1  0  0  0  0
 11 43  1  0  0  0  0
  9 44  1  0  0  0  0
  5 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  4  0  0  0
 49 50  1  0  0  0  0
 47 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC3=C(NC4=CC=C(C5C6CCC(O)C(C6CC6N5CCC5=C6NC6=CC=CC=C56)C(=O)OC)C(O)=C34)C2CC1C(=COC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C43H52N4O7/c1-5-22-20-46-16-14-26-36-32(45-39(26)33(46)18-28(22)30(21-52-2)42(50)53-3)12-10-27(41(36)49)40-25-11-13-35(48)37(43(51)54-4)29(25)19-34-38-24(15-17-47(34)40)23-8-6-7-9-31(23)44-38/h6-10,12,21-22,25,28-29,33-35,37,40,44-45,48-49H,5,11,13-20H2,1-4H3

> <INCHI_KEY>
VCDQJQMZNBIPGU-UHFFFAOYSA-N

> <FORMULA>
C43H52N4O7

> <MOLECULAR_WEIGHT>
736.91

> <EXACT_MASS>
736.38360003

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
85.21853100107417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
3.8061147313220545

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.676736532159218

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.582311952402529

> <JCHEM_PKA_STRONGEST_BASIC>
9.280127854929518

> <JCHEM_POLAR_SURFACE_AREA>
140.35000000000002

> <JCHEM_REFRACTIVITY>
206.2867

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      11.108  -1.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.801  -0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.338  -0.296   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.183  -1.584   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      15.721  -1.496   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      16.565  -2.783   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.103  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.795  -1.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.951  -0.032   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      18.914   1.169   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      20.354   0.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.723   1.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.019   0.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.945  -1.041   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.241  -1.873   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.610  -1.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.683   0.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.052   1.076   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.347   0.244   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      29.716   0.950   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.274  -1.294   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.905  -2.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.832  -3.538   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.463  -4.244   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      24.168  -3.412   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      22.799  -4.117   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.726  -5.656   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.021  -6.488   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.390  -5.782   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      26.484  -6.866   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      25.792  -8.242   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.351  -9.677   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.387 -10.878   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.865 -10.645   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.306  -9.210   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      24.270  -8.008   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      29.570  -2.127   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      29.497  -3.665   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      30.938  -1.421   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      32.234  -2.254   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.577  -1.747   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      21.503  -3.285   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      20.281  -0.914   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      16.413  -0.120   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.568   1.167   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.031   1.079   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.186   2.367   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.878   3.742   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      13.033   5.030   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      13.726   6.405   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.648   2.279   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      10.956   0.903   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      10.803   3.566   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      11.496   4.942   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   46                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   44                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   43                                                  
CONECT    9    8   10   44                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   43                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   37                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   15   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   28   31                                                  
CONECT   37   21   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39                                                            
CONECT   41   14   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    8   11                                                  
CONECT   44    9    5   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45    3   47                                                  
CONECT   47   46   48   51                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   47   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  124    0
END

View in JSmol

Synonyms

Value	Source
Methyl 14-[4-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-5-ethyl-12-hydroxy-7,17-diazatetracyclo[8.7.0.0,.0,]heptadeca-1(10),11(16),12,14-tetraen-13-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8-tetraene-19-carboxylic acid	Generator
Methyl 14-[4-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-5-ethyl-12-hydroxy-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),11(16),12,14-tetraen-13-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylic acid	Generator

Chemical Formula

C₄₃H₅₂N₄O₇

Average Mass

736.9100 Da

Monoisotopic Mass

736.38360 Da

IUPAC Name

methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC3=C(NC4=CC=C(C5C6CCC(O)C(C6CC6N5CCC5=C6NC6=CC=CC=C56)C(=O)OC)C(O)=C34)C2CC1C(=COC)C(=O)OC

InChI Identifier

InChI=1S/C43H52N4O7/c1-5-22-20-46-16-14-26-36-32(45-39(26)33(46)18-28(22)30(21-52-2)42(50)53-3)12-10-27(41(36)49)40-25-11-13-35(48)37(43(51)54-4)29(25)19-34-38-24(15-17-47(34)40)23-8-6-7-9-31(23)44-38/h6-10,12,21-22,25,28-29,33-35,37,40,44-45,48-49H,5,11,13-20H2,1-4H3

InChI Key

VCDQJQMZNBIPGU-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
Hydroxyindole
3-alkylindole
Quinolizine
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Aralkylamine
Benzenoid
Piperidine
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Vinylogous ester
Pyrrole
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carbonyl group
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	4.83	ALOGPS
logP	3.81	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.58	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.35 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	206.29 m³·mol⁻¹	ChemAxon
Polarizability	85.22 Å³	ChemAxon
Number of Rings	9	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 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate (NP0292000)

MOL for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D MOL for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D SDF for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D-SDF for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

PDB for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D PDB for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

SMILES for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

INCHI for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

Structure for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D Structure for NP0292000 (methyl 14-[2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-9-yl]-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)