NP-MRD: Showing NP-Card for (5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate (NP0157155)

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Record Information

Version

2.0

Created at

2022-09-02 14:28:41 UTC

Updated at

2022-09-02 14:28:41 UTC

NP-MRD ID

NP0157155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate

Description

Scabrosin diacetate belongs to the class of organic compounds known as epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges. Based on a literature review very few articles have been published on Scabrosin diacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216282D          

 34 41  0  0  1  0            999 V2000
   11.5165    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7898    1.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648    2.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0882    1.0509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3615    1.4415    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6599    1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9333    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5559    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9755    2.3437    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4644    2.9175    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8779    3.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550    4.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    3.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192    4.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    3.9061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3904    4.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816    5.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    5.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    5.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    3.0812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1267    2.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.6763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5468    3.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217    2.7174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    1.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7989    3.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2795    4.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1106    2.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9083    2.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6099    2.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3115    3.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3365    2.2662    0.0000 C   0  0  1  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  1  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  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
  5 34  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 54 61  0  0  0  0  0  0  0  0999 V2000
    9.1808   -0.3473    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7837   -0.8176   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5324   -1.9957   -0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7541    0.0827    0.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -0.2712   -0.2063 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6109   -0.1101    1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929   -0.1682    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951   -0.0520    1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111    0.5109    1.1327 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0061    2.3339    1.1371 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096    2.6188   -0.1535 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    0.8891   -0.7285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1526    0.7887   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293    0.1947   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5439    0.2146   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4268   -0.4773    0.0094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7061    0.1298   -0.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8267   -0.5574   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1659    0.1310   -0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7181   -1.7600   -0.7398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -0.4082    1.3878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1393    0.8218    1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4564   -0.3894    1.5603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6148   -0.5179    0.3196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2993    0.0559    0.4543 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702   -0.0055    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5002   -0.4945    2.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.3322   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810    0.0581   -2.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.1402   -0.2825 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605   -0.3834   -0.4180 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3763    0.4578   -1.4623 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9963    1.6110   -0.9156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817    0.5287   -1.3174 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8500   -1.1974    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648    0.1655   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150    0.3717    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3878   -1.3563   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240    0.0449    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    0.6255    2.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -1.0523    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    0.2285   -2.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4748    1.8044   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0141    0.7350   -1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5404   -1.5326   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9181   -0.5651    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4833    0.3285   -1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1137    1.0708    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5374   -0.7244    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -0.8191    2.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -1.5929    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023   -1.4562   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524    0.5555   -2.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472    0.7441   -2.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 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
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34  5  1  0
 31  7  1  0
 34 32  1  0
 26  9  1  0
 30  9  1  0
 25 12  1  0
 24 14  1  0
 23 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  6
  6 39  1  0
  8 40  1  0
  8 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  6
 19 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  1
 23 50  1  1
 24 51  1  6
 31 52  1  6
 32 53  1  6
 34 54  1  6
M  END


  Mrv1652309022216282D          

 34 41  0  0  1  0            999 V2000
   11.5165    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7898    1.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7648    2.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0882    1.0509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3615    1.4415    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6599    1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9333    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223    1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5559    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9755    2.3437    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4644    2.9175    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8779    3.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550    4.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    3.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192    4.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    3.9061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3904    4.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816    5.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    5.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    5.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    3.0812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1267    2.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.6763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5468    3.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217    2.7174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    1.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7989    3.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2795    4.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1106    2.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9083    2.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6099    2.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3115    3.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3365    2.2662    0.0000 C   0  0  1  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  1  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  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
  5 34  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C=C2CC34SSC5(CC6=C[C@H](OC(C)=O)[C@@H]7O[C@@H]7C6N5C3=O)C(=O)N4C2[C@H]2O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H20N2O8S2/c1-7(25)29-11-3-9-5-21-19(27)24-14-10(4-12(30-8(2)26)16-18(14)32-16)6-22(24,34-33-21)20(28)23(21)13(9)17-15(11)31-17/h3-4,11-18H,5-6H2,1-2H3/t11-,12-,13?,14?,15-,16-,17+,18+,21?,22?/m0/s1

> <INCHI_KEY>
ZBNYTZGPXZDUNM-WANKTZDVSA-N

> <FORMULA>
C22H20N2O8S2

> <MOLECULAR_WEIGHT>
504.53

> <EXACT_MASS>
504.06610796

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
48.36450087517429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,7S,8S,16R,18S,19S)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0^{1,14}.0^{3,12}.0^{4,10}.0^{5,7}.0^{15,21}.0^{16,18}]tetracosa-9,20-dien-8-yl acetate

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.15499073466666707

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.935582497819229

> <JCHEM_POLAR_SURFACE_AREA>
118.27999999999999

> <JCHEM_REFRACTIVITY>
116.85259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,7S,8S,16R,18S,19S)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0^{1,14}.0^{3,12}.0^{4,10}.0^{5,7}.0^{15,21}.0^{16,18}]tetracosa-9,20-dien-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      21.497   2.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.141   2.772   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.094   4.311   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.831   1.962   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      17.475   2.691   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.165   1.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.809   2.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.295   2.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.238   3.399   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      11.154   4.375   0.000  0.00  0.00           S+0
HETATM   11  S   UNK     0      12.067   5.446   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0      10.972   6.420   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.996   7.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.471   7.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.129   8.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.804   7.291   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.462   8.047   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.446   9.587   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.104  10.343   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.771  10.371   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.820   5.752   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.837   4.212   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.162   4.996   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.487   5.780   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       9.934   5.072   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      10.504   3.446   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.597   2.201   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.691   6.395   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.588   7.647   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0      13.273   4.759   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      14.762   4.149   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.072   4.959   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.382   5.769   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      17.428   4.230   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   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   26   30                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25   28                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   21   24                                                  
CONECT   24   23   14   25                                                  
CONECT   25   24   12   26                                                  
CONECT   26   25    9   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    9   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   34                                                       
CONECT   34   33    5   32                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Value	Source
Scabrosin diacetic acid	Generator

Chemical Formula

C₂₂H₂₀N₂O₈S₂

Average Mass

504.5300 Da

Monoisotopic Mass

504.06611 Da

IUPAC Name

(5R,7S,8S,16R,18S,19S)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0^{1,14}.0^{3,12}.0^{4,10}.0^{5,7}.0^{15,21}.0^{16,18}]tetracosa-9,20-dien-8-yl acetate

Traditional Name

(5R,7S,8S,16R,18S,19S)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0^{1,14}.0^{3,12}.0^{4,10}.0^{5,7}.0^{15,21}.0^{16,18}]tetracosa-9,20-dien-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C=C2CC34SSC5(CC6=C[C@H](OC(C)=O)[C@@H]7O[C@@H]7C6N5C3=O)C(=O)N4C2[C@H]2O[C@@H]12

InChI Identifier

InChI=1S/C22H20N2O8S2/c1-7(25)29-11-3-9-5-21-19(27)24-14-10(4-12(30-8(2)26)16-18(14)32-16)6-22(24,34-33-21)20(28)23(21)13(9)17-15(11)31-17/h3-4,11-18H,5-6H2,1-2H3/t11-,12-,13?,14?,15-,16-,17+,18+,21?,22?/m0/s1

InChI Key

ZBNYTZGPXZDUNM-WANKTZDVSA-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 epipolythiodioxopiperazines. Epipolythiodioxopiperazines are compounds containing an epipolythiodioxopiperazine moiety, which consists of a 2,3-dithia-5,7-diazabicyclo[2.2.2]Octane-6,8-dione ring system. One distinct characteristics of Epipolythiodioxopiperazines is the presence of unique di- or polysulfide bridges.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Epipolythiodioxopiperazines

Alternative Parents

Substituents

Epipolythiodioxopiperazine
Alpha-amino acid or derivatives
Indole or derivatives
N-alkylpiperazine
Dithiazinane
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrrolidine
Organic disulfide
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
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
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.44	ALOGPS
logP	0.15	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	118.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.85 m³·mol⁻¹	ChemAxon
Polarizability	48.36 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122201852

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate (NP0157155)

MOL for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

3D MOL for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

3D SDF for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

3D-SDF for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

PDB for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

3D PDB for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

SMILES for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

INCHI for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

Structure for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)

3D Structure for NP0157155 ((5r,7s,8s,16r,18s,19s)-19-(acetyloxy)-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0⁵,⁷.0¹⁵,²¹.0¹⁶,¹⁸]tetracosa-9,20-dien-8-yl acetate)