NP-MRD: Showing NP-Card for Acanthothamine (NP0059550)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 04:46:46 UTC

Updated at

2022-04-28 04:46:46 UTC

NP-MRD ID

NP0059550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acanthothamine

Description

[(1S,3R,13S,14S,17S,18S,19R,20R,21S,22R,23R,24S,25S)-18,19,21-tris(acetyloxy)-22,24,25-trihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]Pentacosa-7(12),8,10-trien-20-yl]methyl acetate belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Acanthothamine is found in Acanthothamnus aphyllus. Based on a literature review very few articles have been published on [(1S,3R,13S,14S,17S,18S,19R,20R,21S,22R,23R,24S,25S)-18,19,21-tris(acetyloxy)-22,24,25-trihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]Pentacosa-7(12),8,10-trien-20-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206462D          

 51 55  0  0  1  0            999 V2000
   10.1710    0.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9887    1.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2007    1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5951    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7775    0.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.3055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9211   -0.9065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1302   -1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2276   -2.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3105   -1.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649   -0.7341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8125   -1.0950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1358   -0.6157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1473    0.2494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9252    0.6170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6176    1.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    1.9912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2643    2.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364    2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9705    1.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396    2.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3447    2.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4599    1.9986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6358    1.3297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8531    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    1.6604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4663    0.8052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6902    0.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598    1.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    0.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972    2.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830    0.0855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0909    0.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4074    0.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5440   -0.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -0.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1518   -0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -0.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568   -1.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485   -2.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430   -1.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -2.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1668   -2.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3505   -3.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3646   -1.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2315   -0.7239    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 23  1  1  0  0  0
 24 18  1  1  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 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
 27 33  1  6  0  0  0
 16 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 15 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 14 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 13 46  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
  8 50  1  6  0  0  0
  7 51  1  1  0  0  0
M  END

     RDKit          3D

 94 98  0  0  0  0  0  0  0  0999 V2000
    5.6267    1.4368   -2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376    0.8348   -2.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172    0.7179   -3.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    0.3883   -1.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1957   -0.2036   -1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.5376   -0.6531 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4260   -1.4712    0.0403 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5741   -1.8608   -0.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669   -1.6104   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0255   -2.0345   -1.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0200   -1.0165    0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -2.7650    0.5247 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5659   -3.8980    0.0212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435   -3.0270    0.2429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0386   -2.4794   -1.1262 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0122   -2.8703   -2.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043   -1.0141   -0.7778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4105   -0.9565    0.5441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640   -2.1343    1.1527 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3479   -1.9361    2.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850   -2.7775    1.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943   -2.4040    0.9493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0754   -2.3401    0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397   -3.3954    0.7487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8982   -1.1848    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6377   -1.4144   -0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4342   -0.4490   -1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4855    0.7692   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7882    0.9744    0.1819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9807    0.0368    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3601    0.5481    2.0212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9206   -0.4621    3.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3777    1.6639    1.8156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8738    2.6025    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9789    1.2313    1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979    1.1008    2.6638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435    0.9699    0.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    1.1945   -0.7613 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4970    1.7722   -0.6737 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3751    2.9198    0.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274    4.1575   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    5.4121    0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9600    4.2877   -1.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824    0.8149    0.0665 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6063    1.3401    0.4423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    1.5453    1.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4091    2.1160    1.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3477    1.2367    2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -0.1299   -1.5239 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6416    0.0184   -2.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208   -0.6587   -1.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4211    1.1500   -2.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5209    2.5352   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    1.0689   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560    0.5679   -2.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749   -1.0957   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8796   -0.9418    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1225   -1.4414   -2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -3.1011   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -1.9994   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0247   -2.8686    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623   -3.9661    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -4.0874    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -2.7992   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -3.0443   -2.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -1.4581    3.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -1.2304    2.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412   -2.9041    2.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610   -3.8968    1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -2.7481    2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6286   -2.3806   -1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9986   -0.6507   -2.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1061    1.5627   -1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2312    1.0752    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4502   -1.4041    2.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224   -0.6306    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611   -0.0852    4.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379    2.2869    2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8640    2.9793    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085    2.1839   -0.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2261    3.5313    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    1.8783   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7856    2.0620   -1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296    6.0150    0.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    5.9642    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172    5.1754    1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8259    0.5740    0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312    2.6078    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666    1.3544    2.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2658    2.9149    2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160   -0.6993   -3.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4312    1.0944   -3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -0.1266   -3.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7651   -0.0806   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 41 43  2  0
 39 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  1  0
 46 48  2  0
 44  6  1  0
  6  5  1  6
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 17 49  1  0
 49 50  1  0
 49 51  1  6
 30 31  1  0
 49 38  1  0
 17  6  1  0
 30 25  1  0
 19 14  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 31 74  1  1
 33 78  1  1
 34 79  1  0
 34 80  1  0
 34 81  1  0
 38 82  1  6
 39 83  1  6
 42 84  1  0
 42 85  1  0
 42 86  1  0
 44 87  1  1
 47 88  1  0
 47 89  1  0
 47 90  1  0
  5 55  1  0
  5 56  1  0
  1 52  1  0
  1 53  1  0
  1 54  1  0
  7 57  1  1
 10 58  1  0
 10 59  1  0
 10 60  1  0
 12 61  1  1
 13 62  1  0
 14 63  1  6
 15 64  1  6
 16 65  1  0
 20 66  1  0
 20 67  1  0
 20 68  1  0
 21 69  1  0
 21 70  1  0
 26 71  1  0
 27 72  1  0
 28 73  1  0
 50 91  1  0
 50 92  1  0
 50 93  1  0
 51 94  1  0
M  END


  Mrv1652304282206462D          

 51 55  0  0  1  0            999 V2000
   10.1710    0.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9887    1.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2007    1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5951    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7775    0.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.3055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9211   -0.9065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1302   -1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2276   -2.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3105   -1.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649   -0.7341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8125   -1.0950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1358   -0.6157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1473    0.2494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9252    0.6170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6176    1.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    1.9912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2643    2.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1364    2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9705    1.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396    2.6609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3447    2.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4599    1.9986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6358    1.3297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8531    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    1.6604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4663    0.8052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6902    0.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598    1.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    0.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    1.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972    2.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830    0.0855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0909    0.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4074    0.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5440   -0.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -0.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1518   -0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -0.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568   -1.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485   -2.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430   -1.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201   -2.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1668   -2.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3505   -3.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3646   -1.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2315   -0.7239    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 23  1  1  0  0  0
 24 18  1  1  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 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
 27 33  1  6  0  0  0
 16 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 15 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 14 42  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 13 46  1  1  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
  8 50  1  6  0  0  0
  7 51  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0059550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](C)C(=O)O[C@H]2[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]3(COC(C)=O)[C@H](OC(C)=O)[C@H](O)[C@@H]4[C@H](O)[C@]3(O[C@@]4(C)COC(=O)C3=CC=CN=C13)[C@@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C34H43NO16/c1-14-15(2)29(42)50-27-24(47-17(4)37)28(49-19(6)39)33(13-45-16(3)36)26(48-18(5)38)23(40)21-25(41)34(33,32(27,8)44)51-31(21,7)12-46-30(43)20-10-9-11-35-22(14)20/h9-11,14-15,21,23-28,40-41,44H,12-13H2,1-8H3/t14-,15-,21+,23+,24+,25-,26+,27-,28-,31-,32-,33+,34-/m0/s1

> <INCHI_KEY>
XXXXUOXJKJTNHS-RBLRWHHSSA-N

> <FORMULA>
C34H43NO16

> <MOLECULAR_WEIGHT>
721.709

> <EXACT_MASS>
721.258184309

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
69.26488277258889

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,3R,13S,14S,17S,18S,19R,20R,21S,22R,23R,24S,25S)-18,19,21-tris(acetyloxy)-22,24,25-trihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0^{1,20}.0^{3,23}.0^{7,12}]pentacosa-7,9,11-trien-20-yl]methyl acetate

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
-1.1252297256666686

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.423776038973969

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.627859043299974

> <JCHEM_PKA_STRONGEST_BASIC>
2.611835409196026

> <JCHEM_POLAR_SURFACE_AREA>
240.60999999999993

> <JCHEM_REFRACTIVITY>
164.49360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,3R,13S,14S,17S,18S,19R,20R,21S,22R,23R,24S,25S)-18,19,21-tris(acetyloxy)-22,24,25-trihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0^{1,20}.0^{3,23}.0^{7,12}]pentacosa-7,9,11-trien-20-yl]methyl acetate

> <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      18.986   1.616   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.646   3.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.175   3.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.044   2.528   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.385   1.026   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      17.855   0.570   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      15.909  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.786  -1.692   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.310  -2.226   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.491  -3.756   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      11.780  -2.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.388  -1.370   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.983  -2.044   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.720  -1.149   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.742   0.466   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.194   1.152   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.486   2.157   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.075   3.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.693   3.937   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.321   3.888   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.878   3.590   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.567   4.967   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.977   5.254   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.325   3.731   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.654   2.482   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.192   1.996   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.784   3.099   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.470   1.503   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.022   0.981   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.845   1.974   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.396   1.452   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.117   3.490   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.595   4.077   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.422   0.160   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.370   1.373   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.960   0.100   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.616  -0.585   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.143  -0.135   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.017  -1.185   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.363  -2.686   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.544  -0.735   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.348  -1.848   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.266  -3.386   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.557  -4.225   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.894  -4.084   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.854  -3.578   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      10.117  -4.458   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      11.511  -3.803   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.988  -5.993   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.614  -2.991   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      17.232  -1.351   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   51                                                  
CONECT    8    7    9   50                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14   46                                                  
CONECT   14   13   15   42                                                  
CONECT   15   14   16   28   37                                             
CONECT   16   15   17   25   34                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   23   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   18   25   27                                                  
CONECT   25   24   16   26                                                  
CONECT   26   25                                                            
CONECT   27   24   28   33                                                  
CONECT   28   27   15   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27                                                            
CONECT   34   16   12   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   15   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   14   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   13   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50    8                                                            
CONECT   51    7                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

View in JSmol

Synonyms

Value	Source
[(1S,3R,13S,14S,17S,18S,19R,20R,21S,22R,23R,24S,25S)-18,19,21-Tris(acetyloxy)-22,24,25-trihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0,.0,.0,]pentacosa-7(12),8,10-trien-20-yl]methyl acetic acid	Generator

Chemical Formula

C₃₄H₄₃NO₁₆

Average Mass

721.7090 Da

Monoisotopic Mass

721.25818 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](C)C(=O)O[C@H]2[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]3(COC(C)=O)[C@H](OC(C)=O)[C@H](O)[C@@H]4[C@H](O)[C@]3(O[C@@]4(C)COC(=O)C3=CC=CN=C13)[C@@]2(C)O

InChI Identifier

InChI=1S/C34H43NO16/c1-14-15(2)29(42)50-27-24(47-17(4)37)28(49-19(6)39)33(13-45-16(3)36)26(48-18(5)38)23(40)21-25(41)34(33,32(27,8)44)51-31(21,7)12-46-30(43)20-10-9-11-35-22(14)20/h9-11,14-15,21,23-28,40-41,44H,12-13H2,1-8H3/t14-,15-,21+,23+,24+,25-,26+,27-,28-,31-,32-,33+,34-/m0/s1

InChI Key

XXXXUOXJKJTNHS-RBLRWHHSSA-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
Acanthothamnus aphyllus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Evoninate alkaloid
Hexacarboxylic acid or derivatives
Terpene lactone
Sesquiterpenoid
Agarofuran
Pyridine carboxylic acid
Oxepane
Pyridine
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.34	ALOGPS
logP	-1.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	2.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	240.61 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	164.49 m³·mol⁻¹	ChemAxon
Polarizability	69.26 Å³	ChemAxon
Number of Rings	5	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

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

163079562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acanthothamine (NP0059550)

MOL for NP0059550 (Acanthothamine)

3D MOL for NP0059550 (Acanthothamine)

3D SDF for NP0059550 (Acanthothamine)

3D-SDF for NP0059550 (Acanthothamine)

PDB for NP0059550 (Acanthothamine)

3D PDB for NP0059550 (Acanthothamine)

SMILES for NP0059550 (Acanthothamine)

INCHI for NP0059550 (Acanthothamine)

Structure for NP0059550 (Acanthothamine)

3D Structure for NP0059550 (Acanthothamine)