NP-MRD: Showing NP-Card for Antibiotic A 21101-III (NP0067728)

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Record Information

Version

2.0

Created at

2022-04-28 12:34:33 UTC

Updated at

2022-04-28 12:34:33 UTC

NP-MRD ID

NP0067728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Antibiotic A 21101-III

Description

Aranotin, also known as L 53185, 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. Aranotin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Antibiotic A 21101-III is found in Arachniotus aurens (Eidam)Schroeter and Streptomyces bingchenggensis. Antibiotic A 21101-III was first documented in 1972 (PMID: 4637543). Based on a literature review a small amount of articles have been published on aranotin (PMID: 20809554) (PMID: 4645597) (PMID: 4645598) (PMID: 4698552).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214342D          

 31 36  0  0  1  0            999 V2000
    4.9071   -2.4560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -1.5970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7230   -1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -0.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1545   -2.0603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4556   -2.9248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3460   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011   -3.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7170   -3.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150   -2.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -3.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -1.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8626   -1.4201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2949   -2.1228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3081   -0.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696   -2.6082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831   -1.9109    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -1.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260   -1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018   -1.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048   -1.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6055   -2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0282   -3.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2074   -3.0304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7614   -2.3364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7757   -3.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1686   -4.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368   -5.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9933   -4.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  5  1  1  0  0  0
 10 16  1  0  0  0  0
 15 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  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  1  0  0  0  0
 27  1  1  1  0  0  0
 21 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 49 54  0  0  0  0  0  0  0  0999 V2000
    2.8029   -0.9233    3.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -0.2933    1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    0.9044    1.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -0.8964    0.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4972   -0.3332   -0.6038 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5947   -0.9124   -1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.3893   -2.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375    0.7965   -3.1455 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760    1.4168   -3.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055    1.0250   -2.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990    1.7229   -2.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    1.1341   -1.1632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4766    2.1736    0.3539 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    0.8185    1.7876 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -0.5632    0.6961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6940   -1.6136    1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0933   -1.2015    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1564   -1.6102    1.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4858   -1.2883    1.4456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0091   -0.1804    0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3128    0.8034    0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    0.9886    0.1141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5930    1.8900   -0.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984   -0.2734   -0.1613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7044    0.0525   -0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031    0.7991   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437    1.2021   -2.4154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -1.0205    0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600   -2.1805    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -0.1528   -0.8559 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -0.1974   -1.5537 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2061   -0.2712    3.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8774    2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682   -1.1916    3.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.7411   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927   -1.8299   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9194   -0.9310   -2.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3328    2.3334   -3.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    2.8250   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5421    1.6115   -3.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861   -1.7341    2.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -2.5806    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833   -2.2862    2.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0679   -0.1361    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9580    1.5348   -0.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5456    1.4335    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3698    2.4961   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536   -0.7731   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -1.0620   -2.2774 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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 12 11  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 15 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31  5  1  0
 31 10  1  0
 26 12  1  0
 30 12  1  0
 25 15  1  0
 24 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  1
  6 36  1  0
  7 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  6
 31 49  1  6
M  END


  Mrv1652304282214342D          

 31 36  0  0  1  0            999 V2000
    4.9071   -2.4560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -1.5970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7230   -1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -0.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1545   -2.0603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4556   -2.9248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3460   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011   -3.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7170   -3.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150   -2.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -3.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -2.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -1.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437   -1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8626   -1.4201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2949   -2.1228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3081   -0.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696   -2.6082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831   -1.9109    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -1.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260   -1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018   -1.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048   -1.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6055   -2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0282   -3.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2074   -3.0304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7614   -2.3364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7757   -3.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1686   -4.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368   -5.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9933   -4.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  5  1  1  0  0  0
 10 16  1  0  0  0  0
 15 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  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  1  0  0  0  0
 27  1  1  1  0  0  0
 21 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C=COC=C2C[C@@]34SS[C@]5(CC6=COC=C[C@H](O)[C@H]6N5C3=O)C(=O)N4[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N2O7S2/c1-10(23)29-14-3-5-28-9-12-7-20-17(25)21-15-11(8-27-4-2-13(15)24)6-19(21,30-31-20)18(26)22(20)16(12)14/h2-5,8-9,13-16,24H,6-7H2,1H3/t13-,14-,15-,16-,19+,20+/m0/s1

> <INCHI_KEY>
HXWOWBFXYUFFKS-PSJNWGMYSA-N

> <FORMULA>
C20H18N2O7S2

> <MOLECULAR_WEIGHT>
462.49

> <EXACT_MASS>
462.055543276

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
43.40845696905697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
-0.03402341566666671

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.033485683685463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2215533619559773

> <JCHEM_POLAR_SURFACE_AREA>
105.61000000000001

> <JCHEM_REFRACTIVITY>
111.71349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5S,12R,15S,16S)-16-hydroxy-2,13-dioxo-8,19-dioxa-23,24-dithia-3,14-diazahexacyclo[10.10.2.0^{1,14}.0^{3,12}.0^{4,10}.0^{15,21}]tetracosa-6,9,17,20-tetraen-5-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  N   UNK     0       9.160  -4.585   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.592  -2.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.950  -2.471   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.486  -1.002   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.888  -3.846   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.450  -5.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.112  -5.954   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.589  -7.418   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.072  -6.275   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.761  -5.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.303  -5.906   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.007  -5.074   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.849  -3.543   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.948  -2.464   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.477  -2.651   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.284  -3.963   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.309  -1.355   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       7.783  -4.869   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0       7.248  -3.567   0.000  0.00  0.00           S+0
HETATM   20  C   UNK     0       9.909  -2.093   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.248  -2.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.697  -2.379   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.009  -3.185   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.197  -4.714   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.119  -5.814   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.587  -5.657   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.755  -4.361   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.781  -6.969   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.515  -8.323   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.709  -9.635   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.054  -8.365   0.000  0.00  0.00           C+0
CONECT    1    2    7   27                                                  
CONECT    2    1    3   19   20                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7    9   18                                             
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    5   10                                                  
CONECT   17   15                                                            
CONECT   18    6   19                                                       
CONECT   19   18    2                                                       
CONECT   20    2   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26    1   21                                                  
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
Antibiotic a 21101-III	ChEBI
Aranotina	ChEBI
Aranotine	ChEBI
Aranotinum	ChEBI
Ariotin	ChEBI
L 53185	ChEBI
Lilly 53185	ChEBI

Chemical Formula

C₂₀H₁₈N₂O₇S₂

Average Mass

462.4900 Da

Monoisotopic Mass

462.05554 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C=COC=C2C[C@@]34SS[C@]5(CC6=COC=C[C@H](O)[C@H]6N5C3=O)C(=O)N4[C@H]12

InChI Identifier

InChI=1S/C20H18N2O7S2/c1-10(23)29-14-3-5-28-9-12-7-20-17(25)21-15-11(8-27-4-2-13(15)24)6-19(21,30-31-20)18(26)22(20)16(12)14/h2-5,8-9,13-16,24H,6-7H2,1H3/t13-,14-,15-,16-,19+,20+/m0/s1

InChI Key

HXWOWBFXYUFFKS-PSJNWGMYSA-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
Arachniotus aurens (Eidam)Schroeter	Plant	KNApSAcK
Streptomyces bingchenggensis	LOTUS Database	35616633

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

Alpha-amino acid or derivatives
Epipolythiodioxopiperazine
N-alkylpiperazine
Dithiazinane
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Organic disulfide
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	0.68	ALOGPS
logP	-0.034	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	111.71 m³·mol⁻¹	ChemAxon
Polarizability	43.41 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00025534

Chemspider ID

8587448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10412012

PDB ID

Not Available

ChEBI ID

88274

Good Scents ID

Not Available

References

General References

Gross U, Nieger M, Brase S: A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin. Chemistry. 2010 Oct 11;16(38):11624-31. doi: 10.1002/chem.201001169. Epub 2010 Aug 31. [PubMed:20809554 ]
Ohler E, Tataruch F, Schmidt U: [Studies in the synthesis of the series of 3.6-epidithio-2,5-dioxo-piperazine antibiotics gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. V. Preparation of epitrithio- and epitetrathio-L-prolyl-L-proline anhydride]. Chem Ber. 1972;105(11):3658-61. doi: 10.1002/cber.19721051119. [PubMed:4637543 ]
Poisel H, Schmidt U: [Studies in the synthesis of the antibiotics Gliotoxin, sporidesmin, Aranotin, and chaetocin. 3. Introduction of alkyl groups and sulfur functions into the 3- and 6-positions of 2.5-dioxopiperazines by electrophilic substitutions]. Chem Ber. 1972;105(2):625-34. doi: 10.1002/cber.19721050228. [PubMed:4645597 ]
Ohler E, Poisel H, Tataruch F, Schmidt U: [Studies in the synthesis of the antibiotics gliotoxin, sporidesmin, aranotin, and chaetocin. IV. Preparation of epidithio-L-prolyl-L-proline anhydride]. Chem Ber. 1972;105(2):635-41. doi: 10.1002/cber.19721050229. [PubMed:4645598 ]
Ohler E, Tataruch F, Schmidt U: [Amino acids and peptides. VI. Synthesis of the 3,6-epidithio-2,5-dioxopiperazine antibiotics gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. VI. Nucleophilic introduction of sulfur functions via sulfones and hydroxy derivates of cyclic dipeptides (dioxopiperazines)]. Chem Ber. 1973;106(1):165-76. doi: 10.1002/cber.19731060120. [PubMed:4698552 ]

Showing NP-Card for Antibiotic A 21101-III (NP0067728)

MOL for NP0067728 (Antibiotic A 21101-III)

3D MOL for NP0067728 (Antibiotic A 21101-III)

3D SDF for NP0067728 (Antibiotic A 21101-III)

3D-SDF for NP0067728 (Antibiotic A 21101-III)

PDB for NP0067728 (Antibiotic A 21101-III)

3D PDB for NP0067728 (Antibiotic A 21101-III)

SMILES for NP0067728 (Antibiotic A 21101-III)

INCHI for NP0067728 (Antibiotic A 21101-III)

Structure for NP0067728 (Antibiotic A 21101-III)

3D Structure for NP0067728 (Antibiotic A 21101-III)