NP-MRD: Showing NP-Card for [(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate (NP0210578)

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Record Information

Version

2.0

Created at

2022-09-05 08:27:43 UTC

Updated at

2022-09-05 08:27:43 UTC

NP-MRD ID

NP0210578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

Description

Ajacusine belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. [(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate is found in Consolida ambigua. Based on a literature review very few articles have been published on Ajacusine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210272D          

 56 64  0  0  1  0            999 V2000
   -0.7037    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436    0.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9545   -2.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -2.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634   -2.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9338   -2.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574   -3.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652   -4.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3924   -5.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119   -5.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -4.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -3.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692   -3.1268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6941   -3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3451   -3.6880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2957   -1.8619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3048   -1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -1.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3783   -2.9004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048   -3.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4369    0.8959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5575    0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4400    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052   -0.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7771   -2.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389   -2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3878   -2.0053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398   -3.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -3.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9490   -4.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4289   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6142   -4.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -3.8692    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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 36 33  1  1  0  0  0
  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  1  0  0  0
 45 44  1  1  0  0  0
 29 45  1  0  0  0  0
 46 45  1  1  0  0  0
 37 46  1  0  0  0  0
 46 47  1  0  0  0  0
 43 47  1  0  0  0  0
 47 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
M  END

     RDKit          3D

108116  0  0  0  0  0  0  0  0999 V2000
    0.8940   -2.9496   -3.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -3.1079   -2.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.9248   -1.2648 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4011   -0.8092    0.5582 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4882    0.2559    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7015   -0.4797    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9421    0.1742    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847    1.4329    0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695   -0.5495   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -1.9219   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3203   -2.6618   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5299   -2.0056   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5450   -0.6458   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3717    0.0990   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4172    1.5116   -0.0770 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095    2.2018    1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1573    1.7675    2.3177 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906    3.5492    0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0119    3.7591   -0.5140 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2052    4.9970   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3940    2.5244   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9202    2.3762   -2.2168 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7765   -2.4444    2.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211   -2.6535    1.4831 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9261   -1.3967    0.8713 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.2804    0.1567   -2.3753 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0515   -0.2401    0.9129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7857    0.3116   -0.5402 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.8733   -0.3532   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -1.2749   -0.5495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1168   -0.9291   -0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.9728   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -1.2953    0.9461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3096   -2.0353    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.0300    1.4951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8490    0.2426    0.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2635    0.1079    1.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1811    0.9621    0.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8966   -3.4446   -2.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0179   -1.0977   -1.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790    0.8145    1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2479   -2.4431   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2707   -3.7373   -0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4295   -2.6073   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4805   -0.1147   -0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6007    4.3246    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1816    3.4595    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0328    3.8177   -0.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8600    5.0371   -1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
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 30 84  1  1
M  END


  Mrv1652309052210272D          

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  8  9  2  0  0  0  0
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 10 11  2  0  0  0  0
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  3 30  1  0  0  0  0
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 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
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  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  6  0  0  0
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 29 45  1  0  0  0  0
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 37 46  1  0  0  0  0
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 43 47  1  0  0  0  0
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 49 50  2  0  0  0  0
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 51 52  2  0  0  0  0
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 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 51 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=CC=CC=C3N3C(=O)C[C@H](C)C3=O)CC[C@@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC(=O)C7=CC=CC=C7)[C@@H]5[C@](O)(CC6OC)[C@@](O)([C@@H](OC)[C@H]23)C14

> <INCHI_IDENTIFIER>
InChI=1S/C43H52N2O11/c1-6-44-21-40(22-55-38(49)25-14-10-11-15-28(25)45-31(46)18-23(2)36(45)47)17-16-30(53-4)42-27-19-26-29(52-3)20-41(50,43(51,39(42)44)35(54-5)34(40)42)32(27)33(26)56-37(48)24-12-8-7-9-13-24/h7-15,23,26-27,29-30,32-35,39,50-51H,6,16-22H2,1-5H3/t23-,26+,27+,29?,30+,32+,33-,34+,35-,39?,40-,41+,42-,43+/m0/s1

> <INCHI_KEY>
UTXPEZCSRQUREP-USXLYEPZSA-N

> <FORMULA>
C43H52N2O11

> <MOLECULAR_WEIGHT>
772.892

> <EXACT_MASS>
772.357110502

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
82.91733469178192

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3R,4S,5R,8R,9S,13S,16R,17R,18S)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_LOGP>
2.370366486333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.992996892798867

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.218982473008198

> <JCHEM_PKA_STRONGEST_BASIC>
9.658283160680039

> <JCHEM_POLAR_SURFACE_AREA>
161.37

> <JCHEM_REFRACTIVITY>
200.67999999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3R,4S,5R,8R,9S,13S,16R,17R,18S)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.314   3.116   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.015   1.527   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.182  -0.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.230  -1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.555  -2.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.782  -3.993   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.871  -5.103   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.412  -5.393   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.476  -4.246   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.774  -6.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.855  -8.130   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.466  -9.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.996  -9.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.914  -8.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.304  -7.073   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -7.222  -5.837   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -8.762  -5.854   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.977  -6.884   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.254  -4.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.019  -3.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.036  -1.936   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.763  -4.367   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.555  -3.090   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.573  -5.414   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.809  -7.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.970  -2.125   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.390  -0.301   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.467   0.070   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.682   1.672   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.584  -0.564   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.041   0.344   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.678   0.617   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.751  -2.251   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.160  -0.366   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.555   1.246   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.680   0.015   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.834  -1.081   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.223  -0.236   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.315   0.925   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.318  -2.659   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.787  -3.979   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.431  -2.924   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.314  -1.920   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.516  -3.304   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.051  -3.971   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.659  -4.410   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      10.057  -3.743   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.034  -6.027   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.555  -6.270   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.105  -7.709   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.134  -8.904   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.613  -8.661   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.063  -7.223   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22                                                            
CONECT   24    5   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   36   45                                             
CONECT   30   29    3   31                                                  
CONECT   31   30   32   33   37                                             
CONECT   32   31                                                            
CONECT   33   31   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33    5   29                                                  
CONECT   37   31   38   39   46                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44   47                                                  
CONECT   44   43   45                                                       
CONECT   45   44   29   46                                                  
CONECT   46   45   37   47                                                  
CONECT   47   46   43   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   51                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₅₂N₂O₁₁

Average Mass

772.8920 Da

Monoisotopic Mass

772.35711 Da

IUPAC Name

[(1S,2R,3R,4S,5R,8R,9S,13S,16R,17R,18S)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=CC=CC=C3N3C(=O)C[C@H](C)C3=O)CC[C@@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC(=O)C7=CC=CC=C7)[C@@H]5[C@](O)(CC6OC)[C@@](O)([C@@H](OC)[C@H]23)C14

InChI Identifier

InChI=1S/C43H52N2O11/c1-6-44-21-40(22-55-38(49)25-14-10-11-15-28(25)45-31(46)18-23(2)36(45)47)17-16-30(53-4)42-27-19-26-29(52-3)20-41(50,43(51,39(42)44)35(54-5)34(40)42)32(27)33(26)56-37(48)24-12-8-7-9-13-24/h7-15,23,26-27,29-30,32-35,39,50-51H,6,16-22H2,1-5H3/t23-,26+,27+,29?,30+,32+,33-,34+,35-,39?,40-,41+,42-,43+/m0/s1

InChI Key

UTXPEZCSRQUREP-USXLYEPZSA-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
Consolida ambigua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Acylaminobenzoic acid or derivatives
1-phenylpyrrolidine
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid imide, n-substituted
Piperidine
Pyrrolidone
2-pyrrolidone
Dicarboximide
Carboxylic acid imide
Cyclic alcohol
Pyrrole
Pyrrolidine
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
1,2-diol
Tertiary amine
Carboxylic acid ester
Lactam
Tertiary aliphatic amine
Dialkyl ether
Ether
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Alcohol
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	2.37	ChemAxon
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	161.37 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	200.68 m³·mol⁻¹	ChemAxon
Polarizability	82.92 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	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

88296998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124201531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate (NP0210578)

MOL for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D MOL for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D SDF for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D-SDF for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

PDB for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D PDB for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

SMILES for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

INCHI for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

Structure for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)

3D Structure for NP0210578 ([(1s,2r,3r,4s,5r,8r,9s,13s,16r,17r,18s)-4-(benzoyloxy)-11-ethyl-8,9-dihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]methyl 2-[(3s)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate)