NP-MRD: Showing NP-Card for (1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate (NP0206194)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 02:20:53 UTC

Updated at

2022-09-05 02:20:54 UTC

NP-MRD ID

NP0206194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate

Description

Epoxycytochalasin H 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. (1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate was first documented in 2009 (PMID: 19479839). Based on a literature review a small amount of articles have been published on Epoxycytochalasin H (PMID: 22344916) (PMID: 32581557) (PMID: 28953997).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204202D          

 36 40  0  0  1  0            999 V2000
    0.4822   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -2.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -3.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -2.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055   -1.0424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1482   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -0.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    0.0389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7608   -0.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8651    0.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.5460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0246    2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230    1.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363    1.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.3772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6641    0.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4706    0.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178   -0.0606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0759   -0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.8459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6110   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -1.0197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7479   -1.7353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1923   -2.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -3.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -3.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3995   -4.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112   -3.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -2.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9405   -1.5660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -0.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5653    0.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.4081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 34  1  1  0  0  0
  5 36  1  0  0  0  0
 17 36  1  0  0  0  0
 24 36  1  0  0  0  0
M  END

     RDKit          3D

 75 79  0  0  0  0  0  0  0  0999 V2000
    0.1945    0.4576   -4.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    0.9813   -2.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    1.8379   -2.7473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    0.5637   -1.8319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5159    0.8786   -0.5332 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5420    1.5359    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    1.6161    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273    1.0424   -1.0309 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4162    2.3002   -1.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220    0.8591   -2.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.0104   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4520   -1.0021    0.2592 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7388   -0.5433    1.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2479   -1.9431    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5996   -1.8195   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273   -1.6711   -1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260   -1.6004   -0.2226 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1410   -2.6625    0.7793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8096   -3.7060    0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597   -2.4971    1.3051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5692   -2.8979    2.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446   -1.6420    0.4961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4858   -1.6619    1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264   -0.1943    0.3375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9902    0.6187    1.5199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6181    1.9396    1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    1.9715    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1295    1.8229    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3493    1.8647    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3753    2.0634   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2154    2.2136   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055    2.1665   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.5572    2.2975 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1966    0.0821    1.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557   -0.0394    2.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212   -0.2816    0.3168 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2799    0.3737   -4.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2626    1.1728   -5.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.4983   -4.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3276    1.6031   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    2.0507    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    2.2050    0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    2.6584   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1284    1.9640   -2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7159    3.0927   -1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    0.3454   -2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6040    0.4911   -0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8018   -0.5315   -1.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3226   -1.7202    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408   -0.3460    1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    0.2940    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595   -1.3763    2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -1.8441    1.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187   -3.0407    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -1.8662   -1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -1.6047   -2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -1.8273   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -3.0236    1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -2.0538    3.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -3.5021    3.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4297   -3.5867    2.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4445   -2.0095   -0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516   -1.8446    2.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028   -2.6155    0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1603   -0.8709    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9472    0.2213   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583    0.0418    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9966    2.7008    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262    2.3258    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0900    1.6685    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2927    1.7460    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3199    2.1009   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2341    2.3682   -2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365    2.2990   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -0.7821    3.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
 24 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 33  1  0
 33 34  2  0
 34 35  1  0
 36 34  1  1
 36 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11  8  1  0
  8  9  1  0
  8 10  1  6
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 36 24  1  0
  5 36  1  0
 20 18  1  0
 32 27  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 22 62  1  6
 24 66  1  6
 25 67  1  1
 26 68  1  0
 26 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  0
 31 73  1  0
 32 74  1  0
 35 75  1  0
 17 57  1  6
 16 56  1  0
 15 55  1  0
 14 53  1  0
 14 54  1  0
 12 49  1  6
 13 50  1  0
 13 51  1  0
 13 52  1  0
 11 47  1  0
 11 48  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
  7 42  1  0
  6 41  1  0
  5 40  1  6
  1 37  1  0
  1 38  1  0
  1 39  1  0
 18 58  1  1
 21 59  1  0
 21 60  1  0
 21 61  1  0
M  END


  Mrv1652309052204202D          

 36 40  0  0  1  0            999 V2000
    0.4822   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -2.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -3.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -2.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055   -1.0424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1482   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -0.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    0.0389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7608   -0.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8651    0.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.5460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0246    2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230    1.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363    1.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.3772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6641    0.5510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4706    0.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178   -0.0606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0759   -0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.8459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6110   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -1.0197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7479   -1.7353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1923   -2.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -3.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -3.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3995   -4.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112   -3.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -2.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9405   -1.5660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -0.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5653    0.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.4081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 34  1  1  0  0  0
  5 36  1  0  0  0  0
 17 36  1  0  0  0  0
 24 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@@]22[C@@H](\C=C/C[C@H](C)C[C@@](C)(O)\C=C/[C@H]2OC(C)=O)[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H39NO5/c1-18-10-9-13-22-26-29(5,36-26)19(2)25-23(16-21-11-7-6-8-12-21)31-27(33)30(22,25)24(35-20(3)32)14-15-28(4,34)17-18/h6-9,11-15,18-19,22-26,34H,10,16-17H2,1-5H3,(H,31,33)/b13-9-,15-14-/t18-,19-,22-,23-,24+,25-,26-,28-,29+,30+/m0/s1

> <INCHI_KEY>
QHZKOXCMCJMHJE-ILIZJMQPSA-N

> <FORMULA>
C30H39NO5

> <MOLECULAR_WEIGHT>
493.644

> <EXACT_MASS>
493.28282336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.44190589996536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3Z,5R,7S,9Z,11R,12S,14R,15S,16R,17S)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-3,9,18-trien-2-yl acetate

> <JCHEM_LOGP>
3.657077936146343

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.672197956075987

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2522842463855253

> <JCHEM_PKA_STRONGEST_BASIC>
5.64822281377948

> <JCHEM_POLAR_SURFACE_AREA>
91.65

> <JCHEM_REFRACTIVITY>
139.71990000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3Z,5R,7S,9Z,11R,12S,14R,15S,16R,17S)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-3,9,18-trien-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.900  -5.133   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.584  -5.253   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.714  -6.853   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.083  -3.917   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.744  -1.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.143  -1.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.759  -1.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.039   0.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.420  -0.869   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.615   0.678   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.612   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.866   2.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.046   4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.283   3.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.801   3.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.939   2.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.334   0.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.840   1.028   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.345   1.353   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.873  -0.113   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.475  -0.395   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.401  -1.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.607  -2.656   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.896  -1.903   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.129  -3.239   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.959  -4.834   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.858  -5.893   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.209  -7.392   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.087  -8.446   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.612  -8.001   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.261  -6.501   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.384  -5.447   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       3.622  -2.923   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.457  -1.392   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.922   0.058   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.862  -0.762   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   36                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   25   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   17   24                                             
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₉NO₅

Average Mass

493.6440 Da

Monoisotopic Mass

493.28282 Da

IUPAC Name

(1R,2R,3Z,5R,7S,9Z,11R,12S,14R,15S,16R,17S)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-3,9,18-trien-2-yl acetate

Traditional Name

(1R,2R,3Z,5R,7S,9Z,11R,12S,14R,15S,16R,17S)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-3,9,18-trien-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@@]22[C@@H](\C=C/C[C@H](C)C[C@@](C)(O)\C=C/[C@H]2OC(C)=O)[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C30H39NO5/c1-18-10-9-13-22-26-29(5,36-26)19(2)25-23(16-21-11-7-6-8-12-21)31-27(33)30(22,25)24(35-20(3)32)14-15-28(4,34)17-18/h6-9,11-15,18-19,22-26,34H,10,16-17H2,1-5H3,(H,31,33)/b13-9-,15-14-/t18-,19-,22-,23-,24+,25-,26-,28-,29+,30+/m0/s1

InChI Key

QHZKOXCMCJMHJE-ILIZJMQPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Cytochalasan
Carbocyclic cytochalasan skeleton
Isoindolone
Isoindole or derivatives
Isoindoline
Oxepane
Benzenoid
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Tertiary alcohol
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
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	3.66	ChemAxon
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	5.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.72 m³·mol⁻¹	ChemAxon
Polarizability	54.44 Å³	ChemAxon
Number of Rings	5	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

C00011335

Chemspider ID

58134665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53316350

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu S, Ge HM, Song YC, Shen Y, Ding H, Tan RX: Cytotoxic cytochalasin metabolites of endophytic Endothia gyrosa. Chem Biodivers. 2009 May;6(5):739-45. doi: 10.1002/cbdv.200800034. [PubMed:19479839 ]
Yang Z, Ge M, Yin Y, Chen Y, Luo M, Chen D: A novel phytotoxic nonenolide from Phomopsis sp. HCCB03520. Chem Biodivers. 2012 Feb;9(2):403-8. doi: 10.1002/cbdv.201100080. [PubMed:22344916 ]
Wang J, Xu Z, Hu X, Yang Y, Su J, Liu Y, Zhou L, Qin J, Zhang D, Yu H: Epoxycytochalasin H: An Endophytic Phomopsis Compound Induces Apoptosis in A2780 Cells Through Mitochondrial Damage and Endoplasmic Reticulum Stress. Onco Targets Ther. 2020 Jun 3;13:4987-4997. doi: 10.2147/OTT.S253716. eCollection 2020. [PubMed:32581557 ]
Ferreira MC, Cantrell CL, Wedge DE, Goncalves VN, Jacob MR, Khan S, Rosa CA, Rosa LH: Antimycobacterial and antimalarial activities of endophytic fungi associated with the ancient and narrowly endemic neotropical plant Vellozia gigantea from Brazil. Mem Inst Oswaldo Cruz. 2017 Oct;112(10):692-697. doi: 10.1590/0074-02760170144. [PubMed:28953997 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate (NP0206194)

MOL for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

3D MOL for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

3D SDF for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

3D-SDF for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

PDB for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

3D PDB for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

SMILES for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

INCHI for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

Structure for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)

3D Structure for NP0206194 ((1r,2r,3z,5r,7s,9z,11r,12s,14r,15s,16r,17s)-17-benzyl-5,19-dihydroxy-5,7,14,15-tetramethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-3,9,18-trien-2-yl acetate)