NP-MRD: Showing NP-Card for 18-Deoxycytochalasin H (NP0061670)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:24:54 UTC

Updated at

2022-04-28 06:24:54 UTC

NP-MRD ID

NP0061670

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-Deoxycytochalasin H

Description

CHEMBL515324 belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. 18-Deoxycytochalasin H is found in Hypoxylon fragiforme (ATCC 20995 MF5511). Based on a literature review very few articles have been published on CHEMBL515324.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208242D          

 35 38  0  0  1  0            999 V2000
    1.4358   -2.4654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6986   -1.7069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4340   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6442   -0.7622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7442   -1.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988   -2.2028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2408   -3.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606   -3.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383   -2.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -3.0071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9001   -3.8168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1199   -4.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274   -4.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -3.5432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6556   -2.7335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1595   -2.0743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6331   -1.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -1.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9139   -1.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0213    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6435   -0.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -3.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -4.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3230   -0.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -0.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0337    0.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    0.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    0.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 11 10  1  1  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  1  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  1  0  0  0
 19 20  2  0  0  0  0
 17 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 15 28  1  1  0  0  0
 12 29  1  6  0  0  0
  7 30  1  1  0  0  0
  5 31  1  1  0  0  0
  2 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
    0.7531    1.9267   -3.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    0.8935   -2.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.3672   -2.9054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0907   -0.3511   -4.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814   -0.5891   -1.7308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7846   -1.5121   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575   -1.3481   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7894   -0.0813   -1.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107   -0.1840    0.1855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6455    1.1383    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5270   -1.3692    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -1.7413    1.8664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1368   -0.9144    3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1684   -2.2596    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -1.6741    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -0.2532    0.7346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0193    0.1834    1.8457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.1530    2.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    1.5161    3.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3584    1.8096    2.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.1357   -0.5995 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1662    1.6111   -0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436    2.4499   -1.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375    2.0130    0.2519 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    1.1449    0.0269 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9446    0.7974    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1583    0.0013    0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347    0.6401    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474   -0.0861   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4335   -1.4650   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -2.1023    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -1.3747    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    0.0465   -0.7386 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7069    0.2402   -2.2273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9611    1.0271   -2.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6892    2.4224   -4.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    2.3738   -4.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    1.1278   -2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -1.1309   -3.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1741   -1.2490   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5414   -2.6084   -1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7604   -2.2150   -1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907    0.7719   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4524    0.0736   -1.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6797   -0.2222   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820    1.9219    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    1.0581    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6450    1.5786    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713   -1.3197    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035   -2.2721    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7946   -2.7018    2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -1.3310    4.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848    0.1366    2.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -0.9977    3.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -3.3860    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994   -2.3072    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383    0.3431    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3345    0.7909    4.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1881    1.5935    4.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8881    2.5496    3.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863    2.8293    0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    1.7859   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5040    0.1399    1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4189    1.7060    1.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3843    1.7117    0.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3599    0.4010   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933   -2.0588   -0.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -3.1918    0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123   -1.9448    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7662   -0.9791   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -0.7775   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606    0.6063   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    0.8577   -3.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8477    2.1242   -2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 34  1  0
 34 33  1  0
 33 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 21 22  1  6
 21  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 34  1  0
 21 33  1  0
 16 21  1  0
 32 27  1  0
 35 72  1  0
 35 73  1  0
 35 74  1  0
 34 71  1  6
 33 70  1  1
 25 62  1  6
 26 63  1  0
 26 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 24 61  1  0
  5 40  1  6
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  6
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  1
 19 58  1  0
 19 59  1  0
 19 60  1  0
  3 38  1  1
  4 39  1  0
  1 36  1  0
  1 37  1  0
M  END


  Mrv1652304282208242D          

 35 38  0  0  1  0            999 V2000
    1.4358   -2.4654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6986   -1.7069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4340   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6442   -0.7622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7442   -1.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988   -2.2028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2408   -3.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606   -3.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383   -2.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -3.0071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9001   -3.8168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1199   -4.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9274   -4.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976   -3.5432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6556   -2.7335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1595   -2.0743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6331   -1.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -1.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9139   -1.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0213    0.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6435   -0.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -3.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -4.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3230   -0.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -0.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0337    0.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    0.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457    0.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 11 10  1  1  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  1  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  1  0  0  0
 19 20  2  0  0  0  0
 17 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 15 28  1  1  0  0  0
 12 29  1  6  0  0  0
  7 30  1  1  0  0  0
  5 31  1  1  0  0  0
  2 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061670

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C[C@H](C)\C=C\[C@H]2OC(C)=O)[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H39NO4/c1-18-10-9-13-24-28(33)21(4)20(3)27-25(17-23-11-7-6-8-12-23)31-29(34)30(24,27)26(35-22(5)32)15-14-19(2)16-18/h6-9,11-15,18-20,24-28,33H,4,10,16-17H2,1-3,5H3,(H,31,34)/b13-9+,15-14+/t18-,19+,20+,24-,25-,26+,27-,28+,30+/m0/s1

> <INCHI_KEY>
JVHIPYJQMFNCEK-ZPSJVCBQSA-N

> <FORMULA>
C30H39NO4

> <MOLECULAR_WEIGHT>
477.645

> <EXACT_MASS>
477.28790874

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.89639648214096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6-hydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.607902504

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.721763010274607

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.0462624716295

> <JCHEM_PKA_STRONGEST_BASIC>
-0.372749375809328

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
139.3526

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6-hydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-2H,3H,4H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl 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       2.680  -4.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.171  -3.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.543  -2.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.291  -1.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.802  -1.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.989  -2.951   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.211  -4.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.916  -5.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.460  -6.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.298  -5.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.842  -5.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.547  -7.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.090  -7.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.731  -9.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.929  -6.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.224  -5.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.298  -3.872   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.182  -2.611   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.654  -3.062   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.467  -1.553   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.320  -3.964   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.034  -2.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.573  -2.503   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.278  -1.134   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.445   0.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.906   0.087   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.201  -1.282   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.540  -7.389   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.362  -8.575   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.803  -3.627   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.070  -0.334   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.284  -1.567   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.930   0.083   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.464   0.556   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.072   1.116   0.000  0.00  0.00           C+0
CONECT    1    2   11   16   19                                             
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    1   12                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15    1   17                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1   20                                                  
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   15                                                            
CONECT   29   12                                                            
CONECT   30    7                                                            
CONECT   31    5                                                            
CONECT   32    2   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
18-Dehydroxycytochalasin H	MeSH

Chemical Formula

C₃₀H₃₉NO₄

Average Mass

477.6450 Da

Monoisotopic Mass

477.28791 Da

IUPAC Name

(3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6-hydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

Traditional Name

(3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6-hydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-2H,3H,4H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C[C@H](C)\C=C\[C@H]2OC(C)=O)[C@H](O)C1=C

InChI Identifier

InChI=1S/C30H39NO4/c1-18-10-9-13-24-28(33)21(4)20(3)27-25(17-23-11-7-6-8-12-23)31-29(34)30(24,27)26(35-22(5)32)15-14-19(2)16-18/h6-9,11-15,18-20,24-28,33H,4,10,16-17H2,1-3,5H3,(H,31,34)/b13-9+,15-14+/t18-,19+,20+,24-,25-,26+,27-,28+,30+/m0/s1

InChI Key

JVHIPYJQMFNCEK-ZPSJVCBQSA-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
Hypoxylon fragiforme (ATCC 20995 MF5511)	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Not Available

Direct Parent

Cytochalasans

Alternative Parents

Substituents

Carbocyclic cytochalasan skeleton
Cytochalasan
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Monocyclic benzene moiety
Benzenoid
2-pyrrolidone
Pyrrolidone
Cyclic alcohol
Pyrrolidine
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactam
Secondary alcohol
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	4.5	ALOGPS
logP	4.61	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	-0.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.35 m³·mol⁻¹	ChemAxon
Polarizability	53.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

4976027

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6473821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 18-Deoxycytochalasin H (NP0061670)

MOL for NP0061670 (18-Deoxycytochalasin H)

3D MOL for NP0061670 (18-Deoxycytochalasin H)

3D SDF for NP0061670 (18-Deoxycytochalasin H)

3D-SDF for NP0061670 (18-Deoxycytochalasin H)

PDB for NP0061670 (18-Deoxycytochalasin H)

3D PDB for NP0061670 (18-Deoxycytochalasin H)

SMILES for NP0061670 (18-Deoxycytochalasin H)

INCHI for NP0061670 (18-Deoxycytochalasin H)

Structure for NP0061670 (18-Deoxycytochalasin H)

3D Structure for NP0061670 (18-Deoxycytochalasin H)