NP-MRD: Showing NP-Card for methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0230992)

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Record Information

Version

2.0

Created at

2022-09-06 11:38:05 UTC

Updated at

2022-09-06 11:38:05 UTC

NP-MRD ID

NP0230992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate

Description

Methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2(7),3,5,9-tetraene-10-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. Based on a literature review very few articles have been published on methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2(7),3,5,9-tetraene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213382D          

 31 35  0  0  1  0            999 V2000
    2.0785    5.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    4.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    4.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    3.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    3.1826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946    1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3073    0.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.2397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4885    1.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.1301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    2.4647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9183    2.9846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4929    3.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634    2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    4.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.9448    0.0000 C   0  0  1  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  2  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  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 16 15  1  6  0  0  0
  6 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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 23 30  1  0  0  0  0
  5 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 19  1  1  0  0  0
 16 31  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -0.1687    4.0727    3.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837    3.1505    2.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    2.7295    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168    3.1971    2.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813    1.7876    0.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    1.3314    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    1.5263    1.0129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    0.5909    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663    0.2580    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741   -0.8047    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1057   -1.1205    0.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853   -2.2215   -0.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198   -1.5498   -0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7038   -1.2354   -1.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -0.1645   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834    0.4033   -0.6315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8993    1.1591   -1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    0.1034   -2.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -0.9480   -2.2015 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -1.3981   -2.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.4006   -2.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -0.4013   -1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464   -0.1849   -0.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347   -0.9134    0.9190 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0468   -0.8542    2.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -0.5902    1.3342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4014   -1.4659    1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -1.0611    1.8625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -2.6465    1.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    1.3174   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3103   -0.5886   -0.8424 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8900    4.4193    3.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    3.4971    4.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8839    4.9045    3.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1925    2.2629    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7699    0.8316    1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7431   -1.9707   -1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -3.1487   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6964   -2.4472   -0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4947   -2.4005   -1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742   -1.8528   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.0989   -1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678    1.4107   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3623   -0.3620   -3.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1581    0.5687   -3.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -1.3846   -4.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -2.4355   -2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2453   -0.7321   -3.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898    0.5771   -3.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2927   -1.4029   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.3363   -1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -2.0204    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    0.0381    2.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -1.6892    2.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0410   -1.1725    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5611   -1.4928    1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8670    0.0416    1.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019   -1.4309    2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    1.8617   -0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    1.5170    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -1.5010   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 23 22  1  6
 23 30  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 23 31  1  0
 30  5  1  0
 16  6  1  0
 31 16  1  0
 15  8  1  0
 31 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  7 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 30 59  1  0
 30 60  1  0
 24 52  1  6
 25 53  1  0
 25 54  1  0
 25 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 31 61  1  1
M  END


  Mrv1652309062213382D          

 31 35  0  0  1  0            999 V2000
    2.0785    5.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486    4.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597    4.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    3.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    3.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    3.1826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    2.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980    1.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946    1.2213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3073    0.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    2.2397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4885    1.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384    0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    1.1301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    2.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    2.4647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9183    2.9846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0482    3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    2.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4929    3.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634    2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3629    4.0243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.9448    0.0000 C   0  0  1  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  2  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  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 16 15  1  6  0  0  0
  6 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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 23 30  1  0  0  0  0
  5 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 19  1  1  0  0  0
 16 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC(OC)=CC=C3[C@@]22CCN3CCC[C@](C1)([C@H](C)OC(C)=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N2O5/c1-14(31-15(2)27)23-8-5-10-26-11-9-24(22(23)26)18-7-6-16(29-3)12-19(18)25-20(24)17(13-23)21(28)30-4/h6-7,12,14,22,25H,5,8-11,13H2,1-4H3/t14-,22-,23-,24-/m0/s1

> <INCHI_KEY>
WQLDCBFCPROBTH-PFPQXOPDSA-N

> <FORMULA>
C24H30N2O5

> <MOLECULAR_WEIGHT>
426.513

> <EXACT_MASS>
426.215472074

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.978982389814036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_LOGP>
1.7685210203333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.596830123812953

> <JCHEM_PKA_STRONGEST_BASIC>
9.823799537231801

> <JCHEM_POLAR_SURFACE_AREA>
77.1

> <JCHEM_REFRACTIVITY>
117.4924

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.880  10.684   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.637   9.163   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.833   8.193   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.271   8.743   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.591   6.672   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.786   5.702   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.308   5.941   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.005   4.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.493   4.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.890   2.680   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.377   2.280   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.774   0.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.799   1.592   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.312   1.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.915   3.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.544   4.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.512   2.983   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.672   1.692   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.863   2.110   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.425   1.559   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.229   2.530   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.472   4.050   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.910   4.601   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.714   5.571   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.957   7.092   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.276   5.021   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.920   5.991   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.358   5.441   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.677   7.512   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.152   6.122   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.106   3.630   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   30                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15    6   17   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30   31                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23    5                                                       
CONECT   31   23   19   16                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₄H₃₀N₂O₅

Average Mass

426.5130 Da

Monoisotopic Mass

426.21547 Da

IUPAC Name

methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl (1R,12R,19R)-12-[(1S)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=CC(OC)=CC=C3[C@@]22CCN3CCC[C@](C1)([C@H](C)OC(C)=O)[C@@H]23

InChI Identifier

InChI=1S/C24H30N2O5/c1-14(31-15(2)27)23-8-5-10-26-11-9-24(22(23)26)18-7-6-16(29-3)12-19(18)25-20(24)17(13-23)21(28)30-4/h6-7,12,14,22,25H,5,8-11,13H2,1-4H3/t14-,22-,23-,24-/m0/s1

InChI Key

WQLDCBFCPROBTH-PFPQXOPDSA-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 aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Carbazole
Indolizidine
Dihydroindole
Indole or derivatives
Anisole
Aralkylamine
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Dicarboxylic acid or derivatives
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Ether
Enamine
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
logP	1.77	ChemAxon
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.49 m³·mol⁻¹	ChemAxon
Polarizability	45.98 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163185837

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,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate (NP0230992)

MOL for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D MOL for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D SDF for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D-SDF for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

PDB for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D PDB for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

SMILES for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

INCHI for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

Structure for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)

3D Structure for NP0230992 (methyl (1r,12r,19r)-12-[(1s)-1-(acetyloxy)ethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate)