NP-MRD: Showing NP-Card for Botryosulfuranol A (NP0019016)

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Record Information

Version

2.0

Created at

2021-01-06 04:34:32 UTC

Updated at

2021-07-15 17:29:48 UTC

NP-MRD ID

NP0019016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Botryosulfuranol A

Provided By

NPAtlas

Description

Botryosulfuranol A is found in Botryosphaeria and Cophinforma mamane. Botryosulfuranol A was first documented in 2019 (PMID: 30576967). Based on a literature review very few articles have been published on (2R,2'R,3S,3'R,3'aR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulfanyl)-3'a,4',5',7'-tetrahydro-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104403D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242104403D          

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    4.9265   -0.4058    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.9749    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -3.0712    0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1449   -2.6548   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -1.2919   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    1.1092    1.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    2.0057   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    3.4984    1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    3.6779    3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    4.0252    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845    0.9309   -2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    1.7210   -2.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    2.6473   -2.2966 H   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  1  0  0  0  0
  4  5  2  0  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  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11  3  1  0  0  0  0
 25 14  1  0  0  0  0
  9  4  1  0  0  0  0
 30 11  1  0  0  0  0
 21 16  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  1  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 23 46  1  1  0  0  0
 24 47  1  0  0  0  0
 27 48  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
 31 51  1  0  0  0  0
 31 52  1  0  0  0  0
 31 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0019016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@]2(SC([H])([H])[H])N(O[C@@]11C(=O)C([H])=C([H])C([H])([H])C1([H])[H])C(=O)[C@]1(OC3=C([H])C([H])=C([H])C([H])=C3[C@]1([H])SC([H])([H])[H])N(C2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O6S2/c1-22-18(27)21(31-3)16(25)19(11-7-6-10-14(19)24)29-23(21)17(26)20(22)15(30-2)12-8-4-5-9-13(12)28-20/h4-6,8-10,15-16,25H,7,11H2,1-3H3/t15-,16+,19-,20-,21+/m0/s1

> <INCHI_KEY>
FWQZEHMYXPCCOA-CEDHKZHLSA-N

> <FORMULA>
C21H22N2O6S2

> <MOLECULAR_WEIGHT>
462.54

> <EXACT_MASS>
462.091928784

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.28620216490681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2'R,3S,3'R,3'aR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulfanyl)-3'a,4',5',7'-tetrahydro-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
3.3726012916666672

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.39370220429849

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.407685713662872

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9326317674022055

> <JCHEM_POLAR_SURFACE_AREA>
96.37999999999998

> <JCHEM_REFRACTIVITY>
116.27179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'R,3S,3'R,3'aR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulfanyl)-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.0551    1.6671   -1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    2.0632   -0.2179 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370    0.7284    0.4983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4618   -0.4464    0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066   -0.7231    1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1273   -1.8891    1.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8987   -2.7619    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -2.4436   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -1.2734   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -0.7182   -1.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.1567   -0.3648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6643   -0.7599    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2511   -1.7536    1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.5248    0.7884 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579   -1.3458    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -0.7127    0.6011 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1200   -1.1097    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5742   -2.4859    0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860   -2.2506   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.5048   -1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -0.9921   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -0.7901   -1.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.7669    0.7350 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1265    1.4553   -0.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443    0.8566    0.8078 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6439    1.6558    2.3626 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    3.3755    2.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5713    1.5293   -0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    2.5506   -0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202    1.0868   -1.0367 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978    1.5902   -2.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329    0.6588   -2.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1635    1.7748   -1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540    2.4417   -2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    1.0317    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967   -0.0619    2.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8914   -2.1505    2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4898   -3.6547    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872   -3.1445   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261   -1.1090    2.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265   -0.4058    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.9749    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -3.0712    0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1449   -2.6548   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -1.2919   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    1.1092    1.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    2.0057   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    3.4984    1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    3.6779    3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    4.0252    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845    0.9309   -2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    1.7210   -2.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    2.6473   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  1
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 11  3  1  0
 25 14  1  0
  9  4  1  0
 30 11  1  0
 21 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  1
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  1
 24 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 31 51  1  0
 31 52  1  0
 31 53  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.055   1.667  -1.887  0.00  0.00           C+0
HETATM    2  S   UNK     0      -3.498   2.063  -0.218  0.00  0.00           S+0
HETATM    3  C   UNK     0      -2.537   0.728   0.498  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.462  -0.446   0.647  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.407  -0.723   1.606  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.127  -1.889   1.503  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.899  -2.762   0.448  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.941  -2.444  -0.492  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.190  -1.273  -0.423  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.188  -0.718  -1.212  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.472   0.157  -0.365  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.664  -0.760   0.518  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.251  -1.754   1.016  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.709  -0.525   0.788  0.00  0.00           N+0
HETATM   15  O   UNK     0       1.758  -1.346   1.046  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.887  -0.713   0.601  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.120  -1.110   1.403  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.574  -2.486   0.903  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.186  -2.251  -0.432  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.482  -1.505  -1.278  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.192  -0.992  -0.827  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.319  -0.790  -1.739  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.652   0.767   0.735  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.127   1.455  -0.377  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.144   0.857   0.808  0.00  0.00           C+0
HETATM   26  S   UNK     0       0.644   1.656   2.363  0.00  0.00           S+0
HETATM   27  C   UNK     0       1.211   3.376   2.330  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.571   1.529  -0.374  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.181   2.551  -0.809  0.00  0.00           O+0
HETATM   30  N   UNK     0      -0.620   1.087  -1.037  0.00  0.00           N+0
HETATM   31  C   UNK     0      -0.898   1.590  -2.333  0.00  0.00           C+0
HETATM   32  H   UNK     0      -3.733   0.659  -2.207  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.163   1.775  -1.988  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.654   2.442  -2.603  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.155   1.032   1.510  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.597  -0.062   2.427  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.891  -2.151   2.246  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.490  -3.655   0.419  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.787  -3.144  -1.301  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.926  -1.109   2.478  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.926  -0.406   1.108  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.237  -2.975   1.614  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.626  -3.071   0.729  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.145  -2.655  -0.714  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.877  -1.292  -2.283  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.070   1.109   1.682  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.906   2.006  -0.090  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.145   3.498   1.751  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.347   3.678   3.409  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.409   4.025   1.892  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.484   0.931  -2.990  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.085   1.721  -2.882  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.293   2.647  -2.297  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   11   35                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8   38                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    3   30                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23   21                                             
CONECT   17   16   18   40   41                                             
CONECT   18   17   19   42   43                                             
CONECT   19   18   20   44                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22   16                                                  
CONECT   22   21                                                            
CONECT   23   16   24   25   46                                             
CONECT   24   23   47                                                       
CONECT   25   23   26   28   14                                             
CONECT   26   25   27                                                       
CONECT   27   26   48   49   50                                             
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   11                                                  
CONECT   31   30   51   52   53                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40   17                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
CONECT   51   31                                                            
CONECT   52   31                                                            
CONECT   53   31                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

RDKit          3D

53 57  0  0  0  0  0  0  0  0999 V2000
   -4.0551    1.6671   -1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    2.0632   -0.2179 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370    0.7284    0.4983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4618   -0.4464    0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066   -0.7231    1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1273   -1.8891    1.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8987   -2.7619    0.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -2.4436   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -1.2734   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -0.7182   -1.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.1567   -0.3648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6643   -0.7599    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2511   -1.7536    1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.5248    0.7884 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579   -1.3458    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -0.7127    0.6011 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1200   -1.1097    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5742   -2.4859    0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860   -2.2506   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -1.5048   -1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -0.9921   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -0.7901   -1.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523    0.7669    0.7350 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1265    1.4553   -0.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443    0.8566    0.8078 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6439    1.6558    2.3626 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    3.3755    2.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5713    1.5293   -0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    2.5506   -0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202    1.0868   -1.0367 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978    1.5902   -2.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329    0.6588   -2.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1635    1.7748   -1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540    2.4417   -2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    1.0317    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967   -0.0619    2.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8914   -2.1505    2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4898   -3.6547    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872   -3.1445   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261   -1.1090    2.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265   -0.4058    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.9749    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -3.0712    0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1449   -2.6548   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766   -1.2919   -2.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    1.1092    1.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    2.0057   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    3.4984    1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    3.6779    3.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    4.0252    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845    0.9309   -2.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    1.7210   -2.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    2.6473   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  1
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 11  3  1  0
 25 14  1  0
  9  4  1  0
 30 11  1  0
 21 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  1
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  1
 24 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 31 51  1  0
 31 52  1  0
 31 53  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,2'r,3S,3'r,3'AR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulphanyl)-3'a,4',5',7'-tetrahydro-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione	Generator
Botryosulphuranol a	Generator

Chemical Formula

C₂₁H₂₂N₂O₆S₂

Average Mass

462.5400 Da

Monoisotopic Mass

462.09193 Da

IUPAC Name

(2R,2'R,3S,3'R,3'aR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulfanyl)-3'a,4',5',7'-tetrahydro-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione

Traditional Name

(2R,2'R,3S,3'R,3'aR)-3'-hydroxy-5'-methyl-3,3'a-bis(methylsulfanyl)-3H,3'H-dispiro[1-benzofuran-2,6'-[1,2]oxazolo[2,3-a]pyrazine-2',1''-cyclohexan]-3''-ene-2'',4',7'-trione

CAS Registry Number

Not Available

SMILES

CS[C@H]1C2=CC=CC=C2O[C@@]11N(C)C(=O)[C@]2(SC)[C@H](O)[C@@]3(CCC=CC3=O)ON2C1=O

InChI Identifier

InChI=1S/C21H22N2O6S2/c1-22-18(27)21(31-3)16(25)19(11-7-6-10-14(19)24)29-23(21)17(26)20(22)15(30-2)12-8-4-5-9-13(12)28-20/h4-6,8-10,15-16,25H,7,11H2,1-3H3/t15-,16+,19-,20-,21+/m0/s1

InChI Key

FWQZEHMYXPCCOA-CEDHKZHLSA-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
Botryosphaeria	NPAtlas	30576967
Cophinforma mamane	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.89	ALOGPS
logP	3.37	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	96.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.27 m³·mol⁻¹	ChemAxon
Polarizability	45.29 Å³	ChemAxon
Number of Rings	5	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

NPAtlas ID

NPA025902

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

146682373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barakat F, Vansteelandt M, Triastuti A, Jargeat P, Jacquemin D, Graton J, Mejia K, Cabanillas B, Vendier L, Stigliani JL, Haddad M, Fabre N: Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L. Phytochemistry. 2019 Feb;158:142-148. doi: 10.1016/j.phytochem.2018.11.007. Epub 2018 Dec 18. [PubMed:30576967 ]

Showing NP-Card for Botryosulfuranol A (NP0019016)

MOL for NP0019016 (Botryosulfuranol A)

3D MOL for NP0019016 (Botryosulfuranol A)

3D SDF for NP0019016 (Botryosulfuranol A)

3D-SDF for NP0019016 (Botryosulfuranol A)

PDB for NP0019016 (Botryosulfuranol A)

3D PDB for NP0019016 (Botryosulfuranol A)

SMILES for NP0019016 (Botryosulfuranol A)

INCHI for NP0019016 (Botryosulfuranol A)

Structure for NP0019016 (Botryosulfuranol A)

3D Structure for NP0019016 (Botryosulfuranol A)