NP-MRD: Showing NP-Card for Linearilin (NP0074147)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 19:18:53 UTC

Updated at

2022-04-28 19:18:53 UTC

NP-MRD ID

NP0074147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linearilin

Description

(1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecane-8,13-diol belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position. Linearilin is found in Delphinium linearilobum. Based on a literature review very few articles have been published on (1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecane-8,13-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221182D          

 33 38  0  0  1  0            999 V2000
    0.6564   -1.0270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083   -1.1495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0200    1.7195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    2.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091   -0.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704   -1.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2284   -1.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864   -2.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -3.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197   -2.6869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  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  1  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 13 18  1  1  0  0  0
 11 19  1  1  0  0  0
 19 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 21 24  1  6  0  0  0
 24 25  1  0  0  0  0
  6 26  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
  5 29  1  6  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
  1 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
   -2.4921   -1.1298    3.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9981   -1.4973    1.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -0.8885    0.7363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -1.2287   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216   -0.3946   -1.6567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4800   -1.0927   -2.8548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    0.8356   -1.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2932    1.4368   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820    1.8142    0.0264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9511    2.3590    1.2747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146    3.7398    1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8642    0.7524   -0.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9726    0.0367   -1.4622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2056   -1.2339   -1.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8851   -2.3195   -1.8562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -2.9073   -2.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.4183    0.2273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3556   -2.7141    0.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851   -3.1424    1.6784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615   -0.4548    0.7907 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3323   -1.0032    0.7156 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4885   -1.7246    1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729   -1.3717   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -0.2737   -0.9190 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5435   -0.4776   -0.9480 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828   -0.5834   -2.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139    1.1184   -0.4325 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4369    1.5427   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709    1.2966    0.1814 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2771    0.4191    1.1496 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6420    1.1176    1.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4980    2.4012    1.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954    2.6403    2.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7861   -0.0721    3.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -1.3309    3.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0897   -1.7337    3.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0825   -2.6253    1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0895   -1.1869    1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.0373   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8793   -2.3230   -0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -0.6782   -3.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.5275   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683    1.5925   -2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572    0.9013    0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8436    2.4215   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6269    2.6494   -0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    4.1577    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9165    4.1350    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9759    4.1826    2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6938    0.6198   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -1.1796   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -2.1423   -3.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133   -3.2547   -2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -3.7437   -3.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -4.1233    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439   -0.1636    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359   -1.9442    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1932   -2.1884   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.8675    0.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.2602   -2.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1779   -0.7423   -2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    0.2137   -2.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648   -1.5344   -2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089    1.7919   -0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476    2.6590   -1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    1.1320   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016    2.2550    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910    0.5864    2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3380    0.4983    1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362    1.9552    3.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253    3.6653    3.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648    2.5335    2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12  9  1  6
 12 29  1  0
 29 28  1  0
 28 27  1  0
 27 31  1  0
 31 32  1  0
 32 33  1  0
 31 30  1  0
 30 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 17  1  0
 17 18  1  6
 18 19  1  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  1  0
 17 20  1  0
 20  3  1  0
 13  5  1  0
 13 12  1  0
 20 12  1  0
 30 29  1  0
 24 27  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  4 39  1  0
  4 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 11 47  1  0
 11 48  1  0
 11 49  1  0
 29 67  1  1
 28 65  1  0
 28 66  1  0
 27 64  1  1
 31 69  1  1
 33 70  1  0
 33 71  1  0
 33 72  1  0
 30 68  1  1
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
 26 61  1  0
 26 62  1  0
 26 63  1  0
 19 55  1  0
 14 51  1  6
 16 52  1  0
 16 53  1  0
 16 54  1  0
 13 50  1  6
 20 56  1  1
M  END


  Mrv1652304282221182D          

 33 38  0  0  1  0            999 V2000
    0.6564   -1.0270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083   -1.1495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0200    1.7195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055    2.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091   -0.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704   -1.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2284   -1.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864   -2.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -3.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197   -2.6869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  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  1  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 13 18  1  1  0  0  0
 11 19  1  1  0  0  0
 19 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 21 24  1  6  0  0  0
 24 25  1  0  0  0  0
  6 26  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
  5 29  1  6  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
  1 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(O)CC[C@@H](OC)[C@]34[C@@H]5C[C@H]6[C@@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC)[C@](OO)([C@@H](OC)[C@@H]23)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO8/c1-6-25-11-21(26)8-7-15(30-3)23-13-9-12-14(29-2)10-22(27,16(13)17(12)31-4)24(33-28,20(23)25)19(32-5)18(21)23/h12-20,26-28H,6-11H2,1-5H3/t12-,13-,14+,15-,16-,17-,18+,19+,20-,21+,22-,23-,24+/m1/s1

> <INCHI_KEY>
OJTGVRVXRXFTNU-OYROXQJZSA-N

> <FORMULA>
C24H39NO8

> <MOLECULAR_WEIGHT>
469.575

> <EXACT_MASS>
469.26756722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.9107506161143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-8,13-diol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-1.1226937470000002

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.41766945328025

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66858487635984

> <JCHEM_PKA_STRONGEST_BASIC>
9.098960714092215

> <JCHEM_POLAR_SURFACE_AREA>
110.08000000000003

> <JCHEM_REFRACTIVITY>
116.84469999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-8,13-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.225  -1.917   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.020  -1.916   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.136  -2.146   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.510  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.359   0.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.721   0.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.176  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659   0.968   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.967   2.178   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.730   1.187   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.493  -0.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.500  -1.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.890  -1.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.767   0.123   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.798   1.598   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.771   3.210   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.864   4.395   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.505  -2.905   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.110  -0.409   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.960  -1.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.464  -0.914   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.119   0.216   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.467  -0.851   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.998  -2.865   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.486  -3.725   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.538  -1.173   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.293  -2.014   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.003  -1.970   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.028   2.264   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.841  -4.163   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.360  -5.769   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.727  -3.624   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.650  -5.016   0.000  0.00  0.00           O+0
CONECT    1    2   13   26   32                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23   29                                             
CONECT    6    5    7   26                                                  
CONECT    7    6    2    8   21                                             
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12    1   14   18                                             
CONECT   14   13    8   15                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   11   20                                                       
CONECT   20   19                                                            
CONECT   21    7   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5                                                       
CONECT   24   21   25                                                       
CONECT   25   24                                                            
CONECT   26    6    1   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    5                                                            
CONECT   30    3   31                                                       
CONECT   31   30                                                            
CONECT   32    1   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉NO₈

Average Mass

469.5750 Da

Monoisotopic Mass

469.26757 Da

IUPAC Name

(1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-8,13-diol

Traditional Name

(1R,2R,3R,4R,5R,6S,8R,9R,10R,13R,16R,17S,18S)-11-ethyl-9-hydroperoxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-8,13-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(O)CC[C@@H](OC)[C@]34[C@@H]5C[C@H]6[C@@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC)[C@](OO)([C@@H](OC)[C@@H]23)[C@H]14

InChI Identifier

InChI=1S/C24H39NO8/c1-6-25-11-21(26)8-7-15(30-3)23-13-9-12-14(29-2)10-22(27,16(13)17(12)31-4)24(33-28,20(23)25)19(32-5)18(21)23/h12-20,26-28H,6-11H2,1-5H3/t12-,13-,14+,15-,16-,17-,18+,19+,20-,21+,22-,23-,24+/m1/s1

InChI Key

OJTGVRVXRXFTNU-OYROXQJZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Delphinium linearilobum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Lappaconitine-type diterpenoid alkaloids

Alternative Parents

Substituents

Lappaconitine-type diterpenoid alkaloid
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Hydroperoxide
1,2-aminoalcohol
Alkyl hydroperoxide
Azacycle
Organoheterocyclic compound
Peroxol
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.4	ALOGPS
logP	-1.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.08 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.84 m³·mol⁻¹	ChemAxon
Polarizability	49.91 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162955234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Linearilin (NP0074147)

MOL for NP0074147 (Linearilin)

3D MOL for NP0074147 (Linearilin)

3D SDF for NP0074147 (Linearilin)

3D-SDF for NP0074147 (Linearilin)

PDB for NP0074147 (Linearilin)

3D PDB for NP0074147 (Linearilin)

SMILES for NP0074147 (Linearilin)

INCHI for NP0074147 (Linearilin)

Structure for NP0074147 (Linearilin)

3D Structure for NP0074147 (Linearilin)