NP-MRD: Showing NP-Card for (-)-Leptosin R (NP0068643)

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Record Information

Version

2.0

Created at

2022-04-28 13:53:34 UTC

Updated at

2022-04-28 13:53:34 UTC

NP-MRD ID

NP0068643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Leptosin R

Description

(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-10,12,14-trien-9-yl]-5-methyl-4-(methylsulfanyl)-4-(propan-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-7,10,12,14-tetraene-3,6-dione 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. (-)-Leptosin R is found in Leptosphaeria sp. Based on a literature review very few articles have been published on (1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-10,12,14-trien-9-yl]-5-methyl-4-(methylsulfanyl)-4-(propan-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-7,10,12,14-tetraene-3,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215532D          

 47 54  0  0  1  0            999 V2000
    0.8967   -0.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -1.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0398   -1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -0.7077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3643   -1.4544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7625   -2.0187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829   -1.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432   -0.5923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8349   -0.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 38 47  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282215532D          

 47 54  0  0  1  0            999 V2000
    0.8967   -0.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -1.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0137   -0.7077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3643   -1.4544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7625   -2.0187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829   -1.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432   -0.5923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6156   -0.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1837    0.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2225   -0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6995    0.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7416   -0.8104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5863   -1.6206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8070   -1.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6475   -2.7406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2425   -2.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0680   -1.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846   -0.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    0.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278   -1.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    2.0147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8143    0.9283    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306    0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1823    1.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1122    2.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311    2.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349   -0.2879    0.0000 C   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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 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
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 17 20  1  1  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 11 23  1  1  0  0  0
  7 24  1  6  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 26 31  1  0  0  0  0
 32 31  1  1  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 24 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  2  0  0  0  0
 39 42  1  6  0  0  0
 42 43  1  0  0  0  0
 39 44  1  1  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 38 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS[C@@]1(C(C)C)N(C)C(=O)C2=C[C@]3([C@H](NC4=C3C=CC=C4)N2C1=O)[C@]12[C@@H](NC3=CC=CC=C13)N1C(=O)[C@H](CO)N(C)C(=O)[C@@]1(O)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C33H36N6O7S/c1-16(2)33(47-5)29(45)38-21(23(41)37(33)4)14-30(17-10-6-8-12-19(17)34-26(30)38)31-18-11-7-9-13-20(18)35-27(31)39-24(42)22(15-40)36(3)28(44)32(39,46)25(31)43/h6-14,16,22,25-27,34-35,40,43,46H,15H2,1-5H3/t22-,25-,26+,27-,30-,31+,32-,33+/m0/s1

> <INCHI_KEY>
NNPYEQIXQDOJPG-DTTCYAGKSA-N

> <FORMULA>
C33H36N6O7S

> <MOLECULAR_WEIGHT>
660.75

> <EXACT_MASS>
660.236618697

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
66.10254114923659

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-5-methyl-4-(methylsulfanyl)-4-(propan-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-7,10(15),11,13-tetraene-3,6-dione

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
0.48456588999999883

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.56114397904646

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.234456197711813

> <JCHEM_PKA_STRONGEST_BASIC>
2.1141833613839704

> <JCHEM_POLAR_SURFACE_AREA>
165.99

> <JCHEM_REFRACTIVITY>
174.44450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-4-isopropyl-5-methyl-4-(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-7,10(15),11,13-tetraene-3,6-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       1.674  -1.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.384  -2.618   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.353  -3.530   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.808  -3.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.098  -1.513   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.129  -0.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.626  -1.321   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.280  -2.715   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.157  -3.768   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.808  -2.523   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.294  -1.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.749  -0.268   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.943   1.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.749  -0.600   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.639   0.763   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      10.718  -1.513   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      10.428  -3.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.973  -3.530   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.675  -5.116   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.653  -4.099   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.194  -3.716   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.291  -1.076   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.408   0.760   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.499   0.265   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.409   1.275   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       5.440   2.520   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.788   1.275   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.848  -0.980   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.239  -1.880   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      -0.121   0.265   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.287   3.761   0.000  0.00  0.00           O+0
HETATM   42  S   UNK     0      -1.520   1.733   0.000  0.00  0.00           S+0
HETATM   43  C   UNK     0      -3.044   1.177   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.340   3.451   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.209   4.971   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.551   4.569   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.559  -0.537   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   24                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   18                                                  
CONECT   11   10   12   14   23                                             
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   10   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22   16                                                            
CONECT   23   11                                                            
CONECT   24    7   25   32   35                                             
CONECT   25   24   26   30                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   26   32                                                       
CONECT   32   31   24   33                                                  
CONECT   33   32   34   40                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   24                                                       
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   47                                                  
CONECT   39   38   40   42   44                                             
CONECT   40   39   33   41                                                  
CONECT   41   40                                                            
CONECT   42   39   43                                                       
CONECT   43   42                                                            
CONECT   44   39   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   38                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-Dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0,.0,]hexadeca-10,12,14-trien-9-yl]-5-methyl-4-(methylsulphanyl)-4-(propan-2-yl)-2,5,16-triazatetracyclo[7.7.0.0,.0,]hexadeca-7,10,12,14-tetraene-3,6-dione	Generator

Chemical Formula

C₃₃H₃₆N₆O₇S

Average Mass

660.7500 Da

Monoisotopic Mass

660.23662 Da

IUPAC Name

(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-5-methyl-4-(methylsulfanyl)-4-(propan-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-7,10(15),11,13-tetraene-3,6-dione

Traditional Name

(1R,4R,9R)-9-[(1S,4S,7S,8S,9S)-7,8-dihydroxy-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-4-isopropyl-5-methyl-4-(methylsulfanyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-7,10(15),11,13-tetraene-3,6-dione

CAS Registry Number

Not Available

SMILES

CS[C@@]1(C(C)C)N(C)C(=O)C2=C[C@]3([C@H](NC4=C3C=CC=C4)N2C1=O)[C@]12[C@@H](NC3=CC=CC=C13)N1C(=O)[C@H](CO)N(C)C(=O)[C@@]1(O)[C@H]2O

InChI Identifier

InChI=1S/C33H36N6O7S/c1-16(2)33(47-5)29(45)38-21(23(41)37(33)4)14-30(17-10-6-8-12-19(17)34-26(30)38)31-18-11-7-9-13-20(18)35-27(31)39-24(42)22(15-40)36(3)28(44)32(39,46)25(31)43/h6-14,16,22,25-27,34-35,40,43,46H,15H2,1-5H3/t22-,25-,26+,27-,30-,31+,32-,33+/m0/s1

InChI Key

NNPYEQIXQDOJPG-DTTCYAGKSA-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
Leptosphaeria sp.	Fungi	KNApSAcK

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
Thiodioxopiperazine
Dihydroindole
Indole
2,5-dioxopiperazine
Dioxopiperazine
N-alkylpiperazine
N-methylpiperazine
Secondary aliphatic/aromatic amine
Benzenoid
Piperazine
1,4-diazinane
Tertiary carboxylic acid amide
Pyrroline
Pyrrolidine
Pyrrole
Secondary alcohol
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Dialkylthioether
Sulfenyl compound
Hemithioaminal
Thioether
Secondary amine
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	2.15	ALOGPS
logP	0.48	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	2.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	165.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	174.44 m³·mol⁻¹	ChemAxon
Polarizability	66.1 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162848011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Leptosin R (NP0068643)

MOL for NP0068643 ((-)-Leptosin R)

3D MOL for NP0068643 ((-)-Leptosin R)

3D SDF for NP0068643 ((-)-Leptosin R)

3D-SDF for NP0068643 ((-)-Leptosin R)

PDB for NP0068643 ((-)-Leptosin R)

3D PDB for NP0068643 ((-)-Leptosin R)

SMILES for NP0068643 ((-)-Leptosin R)

INCHI for NP0068643 ((-)-Leptosin R)

Structure for NP0068643 ((-)-Leptosin R)

3D Structure for NP0068643 ((-)-Leptosin R)