NP-MRD: Showing NP-Card for (+)-Annonacin (NP0078915)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 00:00:23 UTC

Updated at

2022-04-29 00:00:23 UTC

NP-MRD ID

NP0078915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Annonacin

Description

Annonacin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. (+)-Annonacin is found in Annona atemoya, Annona cherimola, Annona densicoma, Annona glabra , Annona montana , Annona muricata , Annona reticulata, Annona salzmanii, Annona senegalensis, Annona spp., Annona squamosa, Asimina longifolia, Asimina parviflora, Asimina triloba, Goniothalamus amuyon, Goniothalamus gardneri, Goniothalamus giganteus, Goniothalamus undulatus and Xylopia aromatica . (+)-Annonacin was first documented in 2019 (PMID: 31695932). Annonacin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32761515) (PMID: 31481122) (PMID: 31357557) (PMID: 30362086).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006262D          

 42 43  0  0  0  0            999 V2000
 9999.789710000.4469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.074310000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.358610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.643110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.927710000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.212210000.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.496610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.781110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.065610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.348110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.632610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.917010000.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.201510000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9170 9999.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2122 9999.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.789710001.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.559310000.4469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.275610000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.989810000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422410000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136610000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852910000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.567110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.283410000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.001810000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.716010000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.432310000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.148510000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.559310001.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.832110001.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9014 9998.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.814410000.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.147010000.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.4018 9999.2598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9990.2269 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.481810000.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.171310000.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.503910000.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7588 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5838 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.838710000.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 17 18  1  0  0  0  0
 17 30  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 33 37  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 32  1  6  0  0  0
 33 31  2  0  0  0  0
 13 37  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  1 39  1  0  0  0  0
 42 17  1  0  0  0  0
 39 38  1  6  0  0  0
 42 38  1  1  0  0  0
M  END

     RDKit          3D

106107  0  0  0  0  0  0  0  0999 V2000
  -13.7304    2.9264   -0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3472    2.5941   -1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1303    1.1302   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8215    0.6067   -1.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6390    1.2628   -0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3304    0.7046   -1.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1782    1.3837   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1476    1.2494    0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1321   -0.0063    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1193   -1.0483    1.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7745   -1.8767    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2211   -1.3586   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201   -0.5990   -0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0319    0.5105    0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072   -1.5219   -0.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6388   -2.6382   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -2.8821   -1.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.6808   -0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0862   -2.1477    0.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9979   -2.7966    1.5938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -1.0807    1.7875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -0.0573    1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567   -0.3951    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -1.2349   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -1.4045   -0.5278 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6039   -2.2120   -1.7046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619   -2.0996    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7404   -2.2589    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4093   -0.8941    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3232   -0.0460    1.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8565    1.3189    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2797    1.4712    0.7467 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1171    0.7779    1.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420    1.3255   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1129    1.5240   -0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0332    1.8174   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3661    1.9277   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8585    3.3468   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1150    1.6615   -2.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7822    1.4169   -2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1436    1.1366   -3.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -0.8275   -0.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1377    2.0710    0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4350    3.2156   -1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6929    3.7792    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6275    3.2184   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3716    2.8559   -2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9331    0.5904   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3101    0.8807    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7740   -0.4717   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7282    0.6881   -2.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7252    1.1423    0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6938    2.3497   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2935   -0.3864   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2574    1.0147   -2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4371    2.5162   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2724    1.2858   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9334    1.9652    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1949    1.8208    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1843   -0.5118    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.3009    2.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1593   -0.6253    2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4199   -1.7992    2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7467   -2.4248    0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1441   -2.7820    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -0.8698   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8819   -2.3141   -1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6337   -0.2269   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    0.7287    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0495   -1.9967    0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648   -3.5596   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736   -2.2714   -2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266   -3.8173   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106   -2.9627   -2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -1.2329   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -2.9782    0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -2.7779    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113   -0.5748    2.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9330   -1.5732    2.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    0.6751    0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208    0.6299    2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4119    0.5798    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4651   -0.8195    1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -0.6823   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6674   -2.2707   -0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634   -0.4126   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -1.6249   -2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650   -3.1383    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730   -1.6480    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360   -2.7353    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8531   -2.8273   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1171   -0.4025   -0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5031   -1.1994   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484    0.0603    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8077   -0.5919    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7480    1.8388    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2035    1.9722    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5441    2.5991    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9835   -0.1871    1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1347    2.1958   -1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3185    0.4469   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9042    1.9808    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0840    1.2024   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3609    3.7560    0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9523    3.3707   -0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5550    3.9391   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 42  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  0
 42 15  1  0
 40 35  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  2 47  1  0
  3 48  1  0
  3 49  1  0
  4 50  1  0
  4 51  1  0
  5 52  1  0
  5 53  1  0
  6 54  1  0
  6 55  1  0
  7 56  1  0
  7 57  1  0
  8 58  1  0
  8 59  1  0
  9 60  1  0
  9 61  1  0
 10 62  1  0
 10 63  1  0
 11 64  1  0
 11 65  1  0
 12 66  1  0
 12 67  1  0
 13 68  1  6
 14 69  1  0
 15 70  1  1
 16 71  1  0
 16 72  1  0
 17 73  1  0
 17 74  1  0
 18 75  1  6
 19 76  1  6
 20 77  1  0
 21 78  1  0
 21 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  0
 24 85  1  0
 25 86  1  6
 26 87  1  0
 27 88  1  0
 27 89  1  0
 28 90  1  0
 28 91  1  0
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  1
 33 99  1  0
 34100  1  0
 34101  1  0
 36102  1  0
 37103  1  1
 38104  1  0
 38105  1  0
 38106  1  0
M  END


  Mrv1652309272006262D          

 42 43  0  0  0  0            999 V2000
 9999.789710000.4469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.074310000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.358610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.643110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.927710000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.212210000.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.496610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.781110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.065610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.348110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.632610000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.917010000.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.201510000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9170 9999.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2122 9999.2096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.789710001.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.559310000.4469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.275610000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.989810000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422410000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136610000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852910000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.567110000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.283410000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.001810000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.716010000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.432310000.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.148510000.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.559310001.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.832110001.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9014 9998.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.814410000.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.147010000.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.4018 9999.2598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9990.2269 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.481810000.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.171310000.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.503910000.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7588 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5838 9999.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.838710000.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 17 18  1  0  0  0  0
 17 30  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 33 37  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 32  1  6  0  0  0
 33 31  2  0  0  0  0
 13 37  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  1 39  1  0  0  0  0
 42 17  1  0  0  0  0
 39 38  1  6  0  0  0
 42 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCC[C@H](O)CCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1

> <INCHI_KEY>
XNODZYPOIPVPRF-CGWDHHCXSA-N

> <FORMULA>
C35H64O7

> <MOLECULAR_WEIGHT>
596.89

> <EXACT_MASS>
596.465204401

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
74.57332773949682

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
6.33

> <JCHEM_LOGP>
7.706254638000002

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.972783524605791

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.312196879753916

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2743091039170382

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
169.3432

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
annonacin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.2748667.501   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.9398666.734   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.6038667.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.2678666.734   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8660.9328667.501   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8659.5968666.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8658.2608667.501   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8656.9258666.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8655.5898667.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8654.2508666.734   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8652.9148667.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8651.5788666.734   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8650.2438667.501   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8651.5788665.191   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8659.5968665.191   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8666.2748669.046   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8671.4448667.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.7818666.734   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8674.1148667.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.4518666.734   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8676.7888667.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8678.1228666.734   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8679.4598667.501   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8680.7928666.734   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8682.1298667.501   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8683.4708666.734   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8684.8038667.501   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8686.1408666.734   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8687.4778667.501   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8671.4448669.046   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8647.6878669.216   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8645.9498664.043   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8647.6548667.655   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0    8646.4088666.750   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0    8646.8838665.285   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8648.4248665.285   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8648.8998666.750   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0    8668.8538667.655   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0    8667.6078666.750   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8668.0838665.285   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8669.6238665.285   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8670.0998666.750   0.000  0.00  0.00           C+0
CONECT    1    2   16   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   37                                                       
CONECT   14   12                                                            
CONECT   15    6                                                            
CONECT   16    1                                                            
CONECT   17   18   30   42                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   17                                                            
CONECT   31   33                                                            
CONECT   32   35                                                            
CONECT   33   37   34   31                                                  
CONECT   34   33   35                                                       
CONECT   35   36   34   32                                                  
CONECT   36   35   37                                                       
CONECT   37   33   36   13                                                  
CONECT   38   39   42                                                       
CONECT   39   40    1   38                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   17   38                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Value	Source
(+)-Annonacin	PhytoBank
Annonacine	PhytoBank

Chemical Formula

C₃₅H₆₄O₇

Average Mass

596.8900 Da

Monoisotopic Mass

596.46520 Da

IUPAC Name

(5S)-5-methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2,5-dihydrofuran-2-one

Traditional Name

annonacin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCC[C@H](O)CCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1

InChI Key

XNODZYPOIPVPRF-CGWDHHCXSA-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
Annona atemoya	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Annona densicoma	Plant	KNApSAcK
Annona glabra	Plant	KNApSAcK
Annona montana	Plant	KNApSAcK
Annona muricata	Plant	KNApSAcK
Annona reticulata	LOTUS Database	35616633
Annona salzmanii	Plant	KNApSAcK
Annona senegalensis	LOTUS Database	35616633
Annona spp.	Plant	KNApSAcK
Annona squamosa	LOTUS Database	35616633
Asimina longifolia	LOTUS Database	35616633
Asimina parviflora	LOTUS Database	35616633
Asimina triloba	LOTUS Database	35616633
Goniothalamus amuyon	LOTUS Database	35616633
Goniothalamus gardneri	LOTUS Database	35616633
Goniothalamus giganteus	LOTUS Database	35616633
Goniothalamus undulatus	LOTUS Database	35616633
Xylopia aromatica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	6.33	ALOGPS
logP	7.71	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	169.34 m³·mol⁻¹	ChemAxon
Polarizability	74.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00043268

Chemspider ID

314587

KEGG Compound ID

C20213

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Annonacin

METLIN ID

Not Available

PubChem Compound

354398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tran K, Ryan S, McDonald M, Thomas AL, Maia JGS, Smith RE: Annonacin and Squamocin Contents of Pawpaw (Asimina triloba) and Marolo (Annona crassiflora) Fruits and Atemoya (A. squamosa x A. cherimola) Seeds. Biol Trace Elem Res. 2021 Jun;199(6):2320-2329. doi: 10.1007/s12011-020-02320-7. Epub 2020 Aug 6. [PubMed:32761515 ]
Virgen-Cecena LJ, Anaya-Esparza LM, Coria-Tellez AV, Garcia-Magana ML, Garcia-Galindo HS, Yahia E, Montalvo-Gonzalez E: Evaluation of nutritional characteristics and bioactive compounds of soursop-yoghurt and soursop-frozen dessert. Food Sci Biotechnol. 2019 Mar 4;28(5):1337-1347. doi: 10.1007/s10068-019-00584-x. eCollection 2019 Oct. [PubMed:31695932 ]
Md Roduan MR, Abd Hamid R, Mohtarrudin N: Modulation of cancer signalling pathway(s) in two -stage mouse skin tumorigenesis by annonacin. BMC Complement Altern Med. 2019 Sep 3;19(1):238. doi: 10.1186/s12906-019-2650-1. [PubMed:31481122 ]
Rodrigues AM, Silva AAS, Pinto CCC, Lima Dos Santos D, Carneiro de Freitas JC, Martins VEP, Maia de Morais S: Larvicidal and Enzymatic Inhibition Effects of Annona muricata Seed Extract and Main Constituent Annonacin against Aedes aegypti and Aedes albopictus (Diptera: Culicidae). Pharmaceuticals (Basel). 2019 Jul 26;12(3):112. doi: 10.3390/ph12030112. [PubMed:31357557 ]
Salama M, El-Desouky S, Alsayed A, El-Hussiny M, Magdy K, Fekry E, Shabka O, El-Khodery SA, Youssef MA, Sobh M, Mohamed W: siRNA Blocking of Mammalian Target of Rapamycin (mTOR) Attenuates Pathology in Annonacin-Induced Tauopathy in Mice. Neurotox Res. 2019 May;35(4):987-992. doi: 10.1007/s12640-018-9974-3. Epub 2018 Oct 25. [PubMed:30362086 ]

Showing NP-Card for (+)-Annonacin (NP0078915)

MOL for NP0078915 ((+)-Annonacin)

3D MOL for NP0078915 ((+)-Annonacin)

3D SDF for NP0078915 ((+)-Annonacin)

3D-SDF for NP0078915 ((+)-Annonacin)

PDB for NP0078915 ((+)-Annonacin)

3D PDB for NP0078915 ((+)-Annonacin)

SMILES for NP0078915 ((+)-Annonacin)

INCHI for NP0078915 ((+)-Annonacin)

Structure for NP0078915 ((+)-Annonacin)

3D Structure for NP0078915 ((+)-Annonacin)