NP-MRD: Showing NP-Card for (1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate (NP0216774)

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Record Information

Version

2.0

Created at

2022-09-05 16:52:20 UTC

Updated at

2022-09-05 16:52:20 UTC

NP-MRD ID

NP0216774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate

Description

Asebotoxin I, also known as acebotoxin III, belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton. (1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate is found in Pieris japonica. (1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate was first documented in 1984 (PMID: 6513201). Based on a literature review very few articles have been published on Asebotoxin I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218522D          

 30 33  0  0  1  0            999 V2000
    1.5967    2.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    1.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    1.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2879    1.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -0.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7462    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6008    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0162    0.1423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6097   -0.6419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0605   -1.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -1.5264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7331   -2.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5017   -0.9780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6431   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772   -0.1534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2539    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584   -0.5279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6429   -0.4359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9951   -1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6115   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8199    0.3457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4586    0.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    1.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -1.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.7582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3413   -1.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299   -0.5387    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  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 11 27  1  6  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    3.7475    3.3160    0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833    2.0672    1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254    0.9699    1.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0095    0.6113    2.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572    0.2942    0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -0.7989    0.7088 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7273   -1.8535   -0.1405 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8152   -2.9997   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515   -2.8080    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496   -1.4399   -0.1180 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8556   -0.3840   -0.1616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5426    1.0063    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8108    1.4248    0.5583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0075    1.2378    1.9286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8398    0.8208   -0.3010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3593    0.5230   -1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -0.3729    0.4722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5088   -0.8099   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.4715   -0.9951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9553    0.4296   -2.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1142    1.5929   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366    2.1087    0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270    2.6879   -1.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3244   -1.3695    0.7750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0288   -2.7429    0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -1.3771    2.1168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -0.4591   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -1.0938   -1.4432 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0619   -1.9812   -2.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801   -0.1888   -1.3720 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    3.7849    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2998    3.0418   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036    4.0043    0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8759    2.3823    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1693    1.7414    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -1.1147    1.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163   -2.0872    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414   -3.3709   -1.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2632   -3.8779    0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -3.6332   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4669   -2.9928    1.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648   -1.6218   -1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    1.4513    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    1.6785   -0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753    2.5461    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    1.9546    2.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6037    1.1605   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    0.0383    1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3339   -1.2092    0.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.4957   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754    0.6878   -0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8364    0.5472   -2.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570    1.4435    1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631    2.2859    1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    3.0720    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    3.1345   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662    2.3230   -2.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    3.5262   -1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -2.6162    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -3.4967    1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -3.0385   -0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5137   -1.8600    2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    0.5594   -2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278   -0.9925   -2.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -1.3796   -3.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6874   -2.8569   -2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -2.2247   -3.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.3776   -2.0375 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 27  1  6
 27 28  1  0
 28 29  1  0
 28 30  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 17 24  1  0
 24 25  1  0
 24 26  1  1
 11  6  1  0
 21 15  1  0
 28  7  1  0
 24 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  6 36  1  1
  7 37  1  1
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  6
 27 63  1  0
 27 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  1
 14 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 18 50  1  0
 19 51  1  6
 20 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
M  END


  Mrv1652309052218522D          

 30 33  0  0  1  0            999 V2000
    1.5967    2.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    1.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    1.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2879    1.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -0.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7462    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6008    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0162    0.1423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6097   -0.6419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0605   -1.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -1.5264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7331   -2.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5017   -0.9780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6431   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772   -0.1534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2539    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584   -0.5279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6429   -0.4359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936   -1.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9951   -1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6115   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8199    0.3457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4586    0.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    1.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -1.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.7582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3413   -1.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299   -0.5387    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  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 11 27  1  6  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0216774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1[C@H]2CC[C@@H]3[C@@]1(C[C@@]2(C)O)C[C@H](O)[C@@]1(O)[C@@H](C[C@H](O)C1(C)C)[C@]3(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O7/c1-6-17(26)30-18-12-7-8-13-21(5,28)14-9-15(24)19(2,3)23(14,29)16(25)10-22(13,18)11-20(12,4)27/h12-16,18,24-25,27-29H,6-11H2,1-5H3/t12-,13+,14+,15+,16+,18?,20-,21-,22+,23+/m1/s1

> <INCHI_KEY>
UVIOAKNWFGGRCJ-FWACMMOASA-N

> <FORMULA>
C23H38O7

> <MOLECULAR_WEIGHT>
426.55

> <EXACT_MASS>
426.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.15136954171999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4R,6S,8S,9R,10R,13R,14R)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl propanoate

> <JCHEM_LOGP>
-0.07275556199999908

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.090123920644512

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.059166212811132

> <JCHEM_PKA_STRONGEST_BASIC>
-2.937297272051553

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
108.73099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4R,6S,8S,9R,10R,13R,14R)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl propanoate

> <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       2.981   5.146   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.182   3.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.960   2.681   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.537   3.270   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.179   1.023   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.874  -0.458   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.649   0.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.393   1.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.988   1.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.764   0.266   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.005  -1.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.846  -2.546   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.374  -2.849   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.102  -4.501   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.537  -1.826   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.800  -3.440   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.491  -0.286   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.941   0.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.882  -0.986   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.533  -0.814   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.015  -2.258   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.324  -3.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.608  -3.829   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.264   0.645   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.456   1.835   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.156   2.338   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.682  -2.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.275  -1.415   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.637  -2.818   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.363  -1.005   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10    6   12   27                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   10   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   11   28                                                       
CONECT   28   27    7   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Acebotoxin III	MeSH
Asebotoxin III	MeSH

Chemical Formula

C₂₃H₃₈O₇

Average Mass

426.5500 Da

Monoisotopic Mass

426.26175 Da

IUPAC Name

(1S,3S,4R,6S,8S,9R,10R,13R,14R)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl propanoate

Traditional Name

(1S,3S,4R,6S,8S,9R,10R,13R,14R)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1[C@H]2CC[C@@H]3[C@@]1(C[C@@]2(C)O)C[C@H](O)[C@@]1(O)[C@@H](C[C@H](O)C1(C)C)[C@]3(C)O

InChI Identifier

InChI=1S/C23H38O7/c1-6-17(26)30-18-12-7-8-13-21(5,28)14-9-15(24)19(2,3)23(14,29)16(25)10-22(13,18)11-20(12,4)27/h12-16,18,24-25,27-29H,6-11H2,1-5H3/t12-,13+,14+,15+,16+,18?,20-,21-,22+,23+/m1/s1

InChI Key

UVIOAKNWFGGRCJ-FWACMMOASA-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
Pieris japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Leucothol and grayanotoxane diterpenoids

Alternative Parents

Substituents

Grayanotoxane diterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	-0.073	ChemAxon
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.73 m³·mol⁻¹	ChemAxon
Polarizability	46.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003404

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

135929163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hotta Y, Ando H, Shirai N, Sakakibara J, Takeya K: Relationship between the inotropy speeds in guinea-pig myocardium and lipophilic character of cardenolides and ericaceous toxins. Jpn J Pharmacol. 1984 Oct;36(2):205-15. doi: 10.1254/jjp.36.205. [PubMed:6513201 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate (NP0216774)

MOL for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

3D MOL for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

3D SDF for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

3D-SDF for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

PDB for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

3D PDB for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

SMILES for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

INCHI for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

Structure for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)

3D Structure for NP0216774 ((1s,3s,4r,6s,8s,9r,10r,13r,14r)-3,4,6,9,14-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl propanoate)