NP-MRD: Showing NP-Card for (1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate (NP0145725)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 00:58:42 UTC

Updated at

2022-09-02 00:58:43 UTC

NP-MRD ID

NP0145725

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate

Description

ANOPTERINE belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate is found in Anopterus glandulosus and Anopterus macleayanus. Based on a literature review very few articles have been published on ANOPTERINE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202582D          

 39 44  0  0  1  0            999 V2000
    5.7550    0.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7880    0.9592    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6271    1.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515    2.0511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3688    2.7820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.2683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6565    1.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    0.5585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3218    0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    1.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    0.3641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4962   -0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.8088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1515    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    0.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7896   -0.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103    0.5889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2250    0.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5198   -0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998   -0.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3345   -0.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8544    0.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439   -1.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    1.4049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3941    2.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2190    2.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    1.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6427    2.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2414    3.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4676    2.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8912    3.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9227    1.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5296   -0.5405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7111   -1.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 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
 16 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36  4  1  1  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 10 39  1  0  0  0  0
M  END

     RDKit          3D

 82 87  0  0  0  0  0  0  0  0999 V2000
    1.3741   -1.8479    4.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819   -1.1839    3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -0.0441    3.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318   -0.1335    2.5346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5635   -0.0719    2.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5220   -0.0083    1.8118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2316   -1.2337    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9926    0.3516    0.4823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2597    1.6932    0.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167   -0.4728   -0.5602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2228   -0.4636   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    0.2118   -1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335    0.2634   -2.1877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5798   -0.9263   -2.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    0.6736   -1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5155    0.1564    0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1287   -1.2827    0.3899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7852   -1.4559    1.8342 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7106   -1.4620    2.1131 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4523   -0.3273    1.4844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0485   -0.8021    0.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.9482    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194   -0.6206    1.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945   -1.4404   -1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719   -1.8271   -2.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3056   -1.5489   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9481   -2.0504   -2.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695    0.9321    1.3045 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1186    1.6099    0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    2.8390    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265    3.3781    1.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028    3.5222   -1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484    2.9857   -2.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    4.6979   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2904    5.4600   -2.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.8050    1.4079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0124   -2.2127   -0.1537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171   -3.3818   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2734   -1.8841   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257   -1.6141    5.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166   -2.6566    4.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329    0.9156    3.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -0.2568    4.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677    0.8169    3.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475   -0.9506    3.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3149    0.7520    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4910   -1.3681    2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289    2.2203    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6015   -1.4971   -0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    0.2492    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7852   -0.1393   -1.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0122   -0.3441   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598    1.2634   -1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    1.0403   -3.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -1.0237   -3.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1115    0.3518   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926    1.7960   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1541   -1.3789   -0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -2.3145    2.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1710   -2.4249    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297   -0.1224    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3287   -1.1900   -3.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267   -2.8817   -2.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -1.7782   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9276   -1.2673   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2961   -1.7158   -3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9190   -1.5586   -2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1052   -3.1393   -2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611    1.6436    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0426    2.6685   -2.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3218    2.1775   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063    3.8129   -3.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    5.1433    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    6.2281   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2396    5.9713   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140    4.7947   -2.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    1.7776    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -3.4701   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -3.4236   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8913   -4.2834   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3297   -2.1875   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0250   -2.5859   -0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 24  2  0
 24 25  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 37  1  0
 37 38  1  0
 37 39  1  0
 39 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 16 15  1  6
 16 36  1  0
 36 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 36  4  1  0
  4  3  1  1
  3  2  1  0
  2  1  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
 28 20  1  0
  2 19  1  0
  4 18  1  0
 16 17  1  0
  8 16  1  0
  8 10  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 26 65  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 20 61  1  1
 19 60  1  1
 18 59  1  1
 17 58  1  6
 38 78  1  0
 38 79  1  0
 38 80  1  0
 39 81  1  0
 39 82  1  0
 11 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  6
 14 55  1  0
 15 56  1  0
 15 57  1  0
 36 77  1  1
 28 69  1  1
 33 70  1  0
 33 71  1  0
 33 72  1  0
 34 73  1  0
 35 74  1  0
 35 75  1  0
 35 76  1  0
  3 42  1  0
  3 43  1  0
  1 40  1  0
  1 41  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  1
  7 47  1  0
  9 48  1  0
M  END


  Mrv1652309022202582D          

 39 44  0  0  1  0            999 V2000
    5.7550    0.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7880    0.9592    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6271    1.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515    2.0511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3688    2.7820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    1.2683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6565    1.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485    0.5585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3218    0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    1.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295    0.3641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4962   -0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.8088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1515    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    0.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7896   -0.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103    0.5889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2250    0.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5198   -0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998   -0.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3345   -0.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8544    0.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4439   -1.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705    1.4049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3941    2.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2190    2.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    1.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6427    2.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2414    3.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4676    2.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8912    3.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9227    1.4071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5296   -0.5405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7111   -1.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 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
 16 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36  4  1  1  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 10 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145725

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@@H]1C2C3C4N(C)C[C@]5(C)C[C@H](O)C[C@]44[C@H]([C@@H]1OC(=O)C(\C)=C\C)[C@@]3(CC2=C)C[C@H](O)[C@]54O

> <INCHI_IDENTIFIER>
InChI=1S/C31H43NO7/c1-8-15(3)26(35)38-22-20-17(5)10-29-13-19(34)31(37)28(6)11-18(33)12-30(31,25(21(20)29)32(7)14-28)24(29)23(22)39-27(36)16(4)9-2/h8-9,18-25,33-34,37H,5,10-14H2,1-4,6-7H3/b15-8+,16-9+/t18-,19-,20?,21?,22+,23+,24+,25?,28-,29-,30-,31-/m0/s1

> <INCHI_KEY>
PISLVTVZMHAKFK-AXLYXMLPSA-N

> <FORMULA>
C31H43NO7

> <MOLECULAR_WEIGHT>
541.685

> <EXACT_MASS>
541.303952729

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.85474536355139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,5S,7S,9S,15R,16S,17R)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2E)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0^{1,13}.0^{4,9}.0^{5,12}.0^{5,17}]nonadecan-15-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.4437031596666667

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.653874402010715

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.032478571121548

> <JCHEM_PKA_STRONGEST_BASIC>
9.721173978336788

> <JCHEM_POLAR_SURFACE_AREA>
116.53000000000002

> <JCHEM_REFRACTIVITY>
145.41219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5S,7S,9S,15R,16S,17R)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2E)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0^{1,13}.0^{4,9}.0^{5,12}.0^{5,17}]nonadecan-15-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.743   1.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245   1.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.319   2.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.071   1.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.771   3.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.136   3.829   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.422   5.193   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.301   2.368   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.092   3.321   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.891   1.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.334   1.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.170   2.327   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.108   0.680   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.926  -0.307   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.055   0.401   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.429   1.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.883   0.042   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.398   0.190   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.941  -0.002   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.099   1.099   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.620   0.857   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.170  -0.582   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.200  -1.777   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.691  -0.824   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.662   0.371   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.241  -2.263   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.762  -2.505   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.278   2.622   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.069   3.944   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.609   3.920   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.358   2.574   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.400   5.241   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.651   6.587   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.939   5.217   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.730   6.539   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.322   2.627   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       4.722  -1.009   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       5.061  -2.511   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.216  -0.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18   36                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   39                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17   36                                             
CONECT   17   16   18   37                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18    2   20                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   20   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   28    4   16                                                  
CONECT   37   17   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   10                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₃NO₇

Average Mass

541.6850 Da

Monoisotopic Mass

541.30395 Da

IUPAC Name

(1S,3S,4S,5S,7S,9S,15R,16S,17R)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2E)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0^{1,13}.0^{4,9}.0^{5,12}.0^{5,17}]nonadecan-15-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@@H]1C2C3C4N(C)C[C@]5(C)C[C@H](O)C[C@]44[C@H]([C@@H]1OC(=O)C(\C)=C\C)[C@@]3(CC2=C)C[C@H](O)[C@]54O

InChI Identifier

InChI=1S/C31H43NO7/c1-8-15(3)26(35)38-22-20-17(5)10-29-13-19(34)31(37)28(6)11-18(33)12-30(31,25(21(20)29)32(7)14-28)24(29)23(22)39-27(36)16(4)9-2/h8-9,18-25,33-34,37H,5,10-14H2,1-4,6-7H3/b15-8+,16-9+/t18-,19-,20?,21?,22+,23+,24+,25?,28-,29-,30-,31-/m0/s1

InChI Key

PISLVTVZMHAKFK-AXLYXMLPSA-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
Anopterus glandulosus	LOTUS Database	35616633
Anopterus macleayanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Piperidine
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Polyol
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

fatty acid ester (CHEBI:2746 )

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	2.04	ALOGPS
logP	2.44	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.41 m³·mol⁻¹	ChemAxon
Polarizability	58.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001614

Chemspider ID

30791215

KEGG Compound ID

C08658

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139031163

PDB ID

Not Available

ChEBI ID

2746

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate (NP0145725)

MOL for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

PDB for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

Structure for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0145725 ((1s,3s,4s,5s,7s,9s,15r,16s,17r)-3,4,7-trihydroxy-9,11-dimethyl-16-{[(2e)-2-methylbut-2-enoyl]oxy}-19-methylidene-11-azahexacyclo[12.3.2.0¹,¹³.0⁴,⁹.0⁵,¹².0⁵,¹⁷]nonadecan-15-yl (2e)-2-methylbut-2-enoate)