NP-MRD: Showing NP-Card for Sporidesmin (NP0051382)

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Record Information

Version

2.0

Created at

2022-04-27 22:46:15 UTC

Updated at

2022-04-27 22:46:15 UTC

NP-MRD ID

NP0051382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sporidesmin

Description

Sporidesmin A belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Sporidesmin is found in Pithomyces chartarum and Pseudopithomyces chartarum. Sporidesmin was first documented in 2000 (PMID: 10947103). Based on a literature review a small amount of articles have been published on sporidesmin A (PMID: 30016827) (PMID: 33918904) (PMID: 28193462) (PMID: 21879298).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200462D          

 30 34  0  0  1  0            999 V2000
    6.3142    0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4860    0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884   -0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166    0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7608   -0.0740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3741   -0.6258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -0.1216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538    0.7646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4094    1.1639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4622    1.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    1.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723    1.8879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    0.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -0.4826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2921   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860   -1.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699   -0.2165    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    0.4965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    1.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450   -1.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4321   -1.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2708   -0.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8837    0.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271    1.4437    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 18 23  1  1  0  0  0
 17 24  1  0  0  0  0
  7 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    6.1557    1.4613   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405    0.6211    0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    0.0317   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.2114   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6237   -2.1110   -0.9021 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -1.7523   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7389   -1.0774   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    0.1688   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    0.7052    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    1.9580    0.6803 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386    2.0068    2.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    0.6889   -0.2653 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    1.6773    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -0.0157   -1.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6892   -0.2176   -0.9797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968    0.5108   -1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633    1.6000   -1.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1822   -0.0116   -0.5373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2644    0.9856   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5724   -1.4755   -1.5894 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -2.5986   -1.4392 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -1.5269   -0.3089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6121   -1.3008    0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463   -1.7787    2.0228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833   -0.5059    0.7682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6081   -0.1623    1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012   -1.9881   -0.0626 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0982   -1.3942    1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3468   -1.3744   -1.2554 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1727   -2.1192   -2.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1684    1.4964    0.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1609    1.1611   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910    2.4797   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -2.7444   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8493    1.9705    2.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321    2.9277    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3113    1.0987    2.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1094    1.9058    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    2.6494    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.3451    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675    0.4797   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    1.8450   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2095    0.5031   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5059    1.4017    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3867    0.9136    2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6808   -0.3352    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -0.7234    2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941   -3.0863   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.0240    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228   -3.0579   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 22 21  1  6
 22 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  6
 29  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
  3  9  1  0
  7  8  1  0
 29 14  1  0
 22 15  1  0
 25 18  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  6
 19 42  1  0
 19 43  1  0
 19 44  1  0
 27 48  1  1
 28 49  1  0
 30 50  1  0
  6 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END


  Mrv1652304282200462D          

 30 34  0  0  1  0            999 V2000
    6.3142    0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4860    0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884   -0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166    0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7608   -0.0740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3741   -0.6258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -0.1216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538    0.7646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4094    1.1639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4622    1.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    1.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723    1.8879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    0.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -0.4826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2921   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860   -1.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699   -0.2165    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    0.4965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    1.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450   -1.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4321   -1.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2708   -0.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8837    0.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271    1.4437    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 18 23  1  1  0  0  0
 17 24  1  0  0  0  0
  7 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2N(C)[C@@H]3N4C(=O)[C@@]5(C)SS[C@]4([C@H](O)[C@]3(O)C2=CC(Cl)=C1OC)C(=O)N5C

> <INCHI_IDENTIFIER>
InChI=1S/C18H20ClN3O6S2/c1-16-14(24)22-13-17(26,12(23)18(22,30-29-16)15(25)21(16)3)7-6-8(19)10(27-4)11(28-5)9(7)20(13)2/h6,12-13,23,26H,1-5H3/t12-,13-,16-,17-,18-/m1/s1

> <INCHI_KEY>
QTONANGUNATZOU-ICTVWZTPSA-N

> <FORMULA>
C18H20ClN3O6S2

> <MOLECULAR_WEIGHT>
473.94

> <EXACT_MASS>
473.0482054

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
44.32937053357805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3S,11R,14R)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.599074866

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.367145641281944

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.876644139067661

> <JCHEM_PKA_STRONGEST_BASIC>
-3.905837756611427

> <JCHEM_POLAR_SURFACE_AREA>
102.78000000000002

> <JCHEM_REFRACTIVITY>
112.7344

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,11R,14R)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.787   1.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.107   0.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.963  -0.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.498  -0.398   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.178   1.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.322   2.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.646   1.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.020  -0.138   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.165  -1.168   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.005  -2.700   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.420  -0.227   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.954   1.427   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.364   2.173   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.463   3.709   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.331   2.036   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.935   3.524   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       2.238   0.714   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.688  -0.901   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.279  -1.532   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.641  -3.028   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       4.050  -0.404   0.000  0.00  0.00           S+0
HETATM   22  S   UNK     0       3.574   0.927   0.000  0.00  0.00           S+0
HETATM   23  C   UNK     0       1.543  -1.931   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.732   1.035   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.187   2.711   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.284  -2.379   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.140  -3.410   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.572  -0.318   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.716   0.713   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      12.931   2.695   0.000  0.00  0.00          Cl+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   25                                             
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   19                                                  
CONECT   12   11   13   15   22                                             
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   21   23                                             
CONECT   19   18   11   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   12                                                       
CONECT   23   18                                                            
CONECT   24   17                                                            
CONECT   25    7                                                            
CONECT   26    3   27                                                       
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(3R,5AR,10BS,11R,11ar)-9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-3,11a-epidithio-11ah-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione	ChEBI
Hydroxysporidesmin b	ChEBI
Sporidesmin	ChEBI
Isosporidesmin b	MeSH
Sporidesmin b	MeSH
Sporidesmin C	MeSH
Sporidesmin D	MeSH
Sporidesmin e	MeSH
Sporidesmin F	MeSH
Sporidesmin g	MeSH
Sporidesmin H	MeSH

Chemical Formula

C₁₈H₂₀ClN₃O₆S₂

Average Mass

473.9400 Da

Monoisotopic Mass

473.04821 Da

IUPAC Name

(1R,2R,3S,11R,14R)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

Traditional Name

(1R,2R,3S,11R,14R)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

CAS Registry Number

Not Available

SMILES

COC1=C2N(C)[C@@H]3N4C(=O)[C@@]5(C)SS[C@]4([C@H](O)[C@]3(O)C2=CC(Cl)=C1OC)C(=O)N5C

InChI Identifier

InChI=1S/C18H20ClN3O6S2/c1-16-14(24)22-13-17(26,12(23)18(22,30-29-16)15(25)21(16)3)7-6-8(19)10(27-4)11(28-5)9(7)20(13)2/h6,12-13,23,26H,1-5H3/t12-,13-,16-,17-,18-/m1/s1

InChI Key

QTONANGUNATZOU-ICTVWZTPSA-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
Pithomyces chartarum	-	KNApSAcK
Pseudopithomyces chartarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Epipolythiodioxopiperazine
Indole
Thiodioxopiperazine
Dioxopiperazine
Anisole
2,5-dioxopiperazine
Dialkylarylamine
N-alkylpiperazine
N-methylpiperazine
Alkyl aryl ether
Benzenoid
Dithiazinane
1,4-diazinane
Piperazine
Aryl halide
Aryl chloride
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Pyrrole
Lactam
Secondary alcohol
Carboxamide group
Organic disulfide
1,2-diol
Azacycle
Carboxylic acid derivative
Ether
Organonitrogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrroloindole (CHEBI:9243 )

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	1.73	ALOGPS
logP	1.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.73 m³·mol⁻¹	ChemAxon
Polarizability	44.33 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002363

Chemspider ID

89980

KEGG Compound ID

C10618

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99596

PDB ID

Not Available

ChEBI ID

9243

Good Scents ID

Not Available

References

General References

Rivera-Chavez J, El-Elimat T, Gallagher JM, Graf TN, Fournier J, Panigrahi GK, Deep G, Bunch RL, Raja HA, Oberlies NH: Delitpyrones: alpha-Pyrone Derivatives from a Freshwater Delitschia sp. Planta Med. 2019 Jan;85(1):62-71. doi: 10.1055/a-0654-5850. Epub 2018 Jul 17. [PubMed:30016827 ]
Fernandez M, Perez V, Fuertes M, Benavides J, Espinosa J, Menendez J, Garcia-Perez AL, Ferreras MC: Pathological Study of Facial Eczema (Pithomycotoxicosis) in Sheep. Animals (Basel). 2021 Apr 9;11(4). pii: ani11041070. doi: 10.3390/ani11041070. [PubMed:33918904 ]
Zhang J, Pan Z, Sheppard A: Both canonical and noncanonical Wnt signalling may be required for detoxification following ETP class mycotoxin exposure. Toxicol Lett. 2017 Apr 5;271:12-19. doi: 10.1016/j.toxlet.2017.02.006. Epub 2017 Feb 11. [PubMed:28193462 ]
Davis C, Gordon N, Murphy S, Singh I, Kavanagh K, Carberry S, Doyle S: Single-pot derivatisation strategy for enhanced gliotoxin detection by HPLC and MALDI-ToF mass spectrometry. Anal Bioanal Chem. 2011 Nov;401(8):2519-29. doi: 10.1007/s00216-011-5344-1. Epub 2011 Aug 31. [PubMed:21879298 ]
Hohenboken WD, Robertson JL, Blodgett DJ, Morris CA, Towers NR: Sporidesmin-induced mortality and histological lesions in mouse lines divergently selected for response to toxins in endophyte-infected fescue. J Anim Sci. 2000 Aug;78(8):2157-63. doi: 10.2527/2000.7882157x. [PubMed:10947103 ]

Showing NP-Card for Sporidesmin (NP0051382)

MOL for NP0051382 (Sporidesmin)

3D MOL for NP0051382 (Sporidesmin)

3D SDF for NP0051382 (Sporidesmin)

3D-SDF for NP0051382 (Sporidesmin)

PDB for NP0051382 (Sporidesmin)

3D PDB for NP0051382 (Sporidesmin)

SMILES for NP0051382 (Sporidesmin)

INCHI for NP0051382 (Sporidesmin)

Structure for NP0051382 (Sporidesmin)

3D Structure for NP0051382 (Sporidesmin)