NP-MRD: Showing NP-Card for (5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione (NP0252918)

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Record Information

Version

2.0

Created at

2022-09-07 16:36:38 UTC

Updated at

2022-09-07 16:36:38 UTC

NP-MRD ID

NP0252918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione

Description

Maremycin G belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Maremycin G 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. (5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione was first documented in 2018 (PMID: 30020298). Based on a literature review very few articles have been published on maremycin G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218362D          

 29 33  0  0  1  0            999 V2000
    3.5464   -2.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -2.5080    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -1.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -1.6468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9328   -1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9117   -0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1870    0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4832   -0.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7585   -0.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6154    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5944    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402   -0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9749    1.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    0.6595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240    1.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6384   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4495   -0.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7244   -0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1882   -1.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3771   -1.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1022   -0.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613   -1.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575   -1.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8496   -2.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134   -3.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9882   -1.7159    0.0000 C   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  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    7.2509    0.9697   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4824    0.8352   -0.5788 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9358   -0.8583   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -1.0128   -0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    0.0314   -0.1648 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4142   -0.0811    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -1.2992   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -2.3411   -0.5313 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.2198   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5148   -3.1869   -1.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -1.4520    0.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6978   -1.7675    1.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -0.1199    0.0178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2782    0.2545   -1.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526    0.5452   -2.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    0.2424   -1.9196 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.4784   -3.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4566   -0.0512   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -0.1442   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -0.3968    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126   -0.5671    1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4384   -0.4808    1.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7459   -0.2241    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384    0.9400    0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.0888    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0543    2.4685    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.9711    0.7283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    3.1345    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086    1.9465    1.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4492    1.8606   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8285    1.0562   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6086    0.0366   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247   -1.1367   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -1.5426   -0.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837   -3.2885   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275   -2.1919   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076   -0.8962    2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2177   -2.3950    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.4338    1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    1.5864   -3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3446   -0.0162   -3.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0806    0.1709   -3.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093   -0.0036   -1.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6059   -0.4644    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3350   -0.7704    2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.6184    2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954    3.7952    2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927    3.7252    0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6126    1.6543    2.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    2.1685    1.8492 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  1  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 13 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
  9  4  1  0
 23 13  1  0
 29 24  1  0
 25  6  1  0
 23 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  8 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 12 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 28 47  1  0
 28 48  1  0
 29 49  1  0
 29 50  1  0
M  END


  Mrv1652309072218362D          

 29 33  0  0  1  0            999 V2000
    3.5464   -2.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -2.5080    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -1.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -1.6468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9328   -1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9117   -0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1870    0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4832   -0.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7585   -0.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6154    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5944    0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402   -0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9749    1.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    0.6595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5240    1.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6384   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4495   -0.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7244   -0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1882   -1.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3771   -1.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1022   -0.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613   -1.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575   -1.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8496   -2.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3134   -3.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9882   -1.7159    0.0000 C   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  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC1=NC2=C(NC1=O)[C@@H](C)C1(C(=O)N(C)C3=CC=CC=C13)C1=C2C(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H21N3O3S/c1-11-18-19(23-14(10-29-3)20(27)24-18)17-13(8-9-16(17)26)22(11)12-6-4-5-7-15(12)25(2)21(22)28/h4-7,11H,8-10H2,1-3H3,(H,24,27)/t11-,22?/m1/s1

> <INCHI_KEY>
NRFFIDZDMKFXMS-FAYKFVSFSA-N

> <FORMULA>
C22H21N3O3S

> <MOLECULAR_WEIGHT>
407.49

> <EXACT_MASS>
407.130362722

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
43.52204532380189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-1',2',3,4,5,7,8,9-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione

> <JCHEM_LOGP>
1.4694826520000013

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.809526806259605

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.099512731032231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4407471894598283

> <JCHEM_POLAR_SURFACE_AREA>
78.84

> <JCHEM_REFRACTIVITY>
114.0965

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.620  -5.417   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       5.267  -4.682   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       5.228  -3.142   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.541  -2.338   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       7.894  -3.074   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.208  -2.270   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.169  -0.731   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.816   0.005   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.502  -0.799   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.149  -0.063   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.482   0.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.443   1.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.835  -0.663   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.957   0.873   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.153   2.186   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      13.455   1.231   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      14.045   2.653   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.258  -0.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.772  -0.364   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.285  -1.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.285  -2.987   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.771  -2.705   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.257  -1.253   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.874  -2.202   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.561  -3.006   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.919  -4.504   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.918  -5.674   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.454  -4.625   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.045  -3.203   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23   24                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   13                                                  
CONECT   24   13   25   29                                                  
CONECT   25   24    6   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(5S)-1',5-Dimethyl-2-[(methylsulfanyl)methyl]-1',2',3,4,5,7,8,9-octahydrospiro[cyclopenta[F]quinoxaline-6,3'- indole]-2',3,9-trione	ChEBI
(5S)-1',5-Dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[F]quinoxaline-6,3'-indole]-2',3,9-trione	ChEBI
(5S)-1',5-Dimethyl-2-[(methylsulphanyl)methyl]-1',2',3,4,5,7,8,9-octahydrospiro[cyclopenta[F]quinoxaline-6,3'- indole]-2',3,9-trione	Generator
(5S)-1',5-Dimethyl-2-[(methylsulphanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[F]quinoxaline-6,3'-indole]-2',3,9-trione	Generator

Chemical Formula

C₂₂H₂₁N₃O₃S

Average Mass

407.4900 Da

Monoisotopic Mass

407.13036 Da

IUPAC Name

(5S)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-1',2',3,4,5,7,8,9-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione

Traditional Name

(5S)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione

CAS Registry Number

Not Available

SMILES

CSCC1=NC2=C(NC1=O)[C@@H](C)C1(C(=O)N(C)C3=CC=CC=C13)C1=C2C(=O)CC1

InChI Identifier

InChI=1S/C22H21N3O3S/c1-11-18-19(23-14(10-29-3)20(27)24-18)17-13(8-9-16(17)26)22(11)12-6-4-5-7-15(12)25(2)21(22)28/h4-7,11H,8-10H2,1-3H3,(H,24,27)/t11-,22?/m1/s1

InChI Key

NRFFIDZDMKFXMS-FAYKFVSFSA-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 indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up 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

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Pyrazine
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Ketone
Lactam
Sulfenyl compound
Thioether
Carboxylic acid derivative
Dialkylthioether
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.47	ChemAxon
pKa (Strongest Acidic)	10.1	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.1 m³·mol⁻¹	ChemAxon
Polarizability	43.52 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

Not Available

Chemspider ID

78441118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585915

PDB ID

Not Available

ChEBI ID

167566

Good Scents ID

Not Available

References

General References

Duan Y, Liu Y, Huang T, Zou Y, Huang T, Hu K, Deng Z, Lin S: Divergent biosynthesis of indole alkaloids FR900452 and spiro-maremycins. Org Biomol Chem. 2018 Aug 1;16(30):5446-5451. doi: 10.1039/c8ob01181h. [PubMed:30020298 ]
LOTUS database [Link]

Showing NP-Card for (5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione (NP0252918)

MOL for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

3D MOL for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

3D SDF for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

3D-SDF for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

PDB for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

3D PDB for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

SMILES for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

INCHI for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

Structure for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)

3D Structure for NP0252918 ((5s)-1',5-dimethyl-2-[(methylsulfanyl)methyl]-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-2',3,9-trione)