NP-MRD: Showing NP-Card for Spiroindimicin D (NP0010871)

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Record Information

Version

1.0

Created at

2021-01-05 20:41:03 UTC

Updated at

2021-07-15 17:07:18 UTC

NP-MRD ID

NP0010871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiroindimicin D

Provided By

NPAtlas

Description

Spiroindimicin D belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Spiroindimicin D is found in Streptomyces. It was first documented in 2012 (PMID: 22694269). Based on a literature review very few articles have been published on Spiroindimicin D (PMID: 34377425).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107423D          

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     RDKit          3D

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  Mrv1652306242107423D          

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   -0.9278   -4.7340    2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -6.2784    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -3.2405    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5206    0.6825    2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.1775    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    1.8965    3.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064    0.1211    3.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    0.9375    4.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177    1.1436    0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    0.6360   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -0.2742   -2.2122 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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 13  5  2  0  0  0  0
 23 14  1  0  0  0  0
 34 24  1  0  0  0  0
 24 12  1  0  0  0  0
 34 28  1  0  0  0  0
 23 17  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  6 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 16 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 22 45  1  0  0  0  0
 25 46  1  0  0  0  0
 25 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
 29 51  1  0  0  0  0
 30 52  1  0  0  0  0
 33 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C(Cl)C([H])=C2C2=C1[C@]1(C3=C([H])C(Cl)=C([H])C([H])=C3N(C([H])([H])[H])C1([H])[H])C1=C(N([H])C(C(=O)OC([H])([H])[H])=C21)C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H19Cl2N3O4/c1-30-10-25(14-9-12(27)5-7-16(14)30)19-18(20(23(31)33-2)29-21(19)24(32)34-3)17-13-8-11(26)4-6-15(13)28-22(17)25/h4-9,28-29H,10H2,1-3H3/t25-/m1/s1

> <INCHI_KEY>
HNJSPDJKLKPYKX-RUZDIDTESA-N

> <FORMULA>
C25H19Cl2N3O4

> <MOLECULAR_WEIGHT>
496.34

> <EXACT_MASS>
495.0752615

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
51.82206121286437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12',14'-dimethyl (3R)-4',5-dichloro-1-methyl-1,2-dihydro-8',13'-diazaspiro[indole-3,10'-tetracyclo[7.6.0.0^{2,7}.0^{11,15}]pentadecane]-1'(9'),2',4',6',11',14'-hexaene-12',14'-dicarboxylate

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
4.9594321059999995

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.54386433341978

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1627460798479605

> <JCHEM_PKA_STRONGEST_BASIC>
2.4008634353310208

> <JCHEM_POLAR_SURFACE_AREA>
87.42

> <JCHEM_REFRACTIVITY>
131.95019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12',14'-dimethyl (3R)-4',5-dichloro-1-methyl-2H-8',13'-diazaspiro[indole-3,10'-tetracyclo[7.6.0.0^{2,7}.0^{11,15}]pentadecane]-1'(9'),2',4',6',11',14'-hexaene-12',14'-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
    5.7833   -0.1468   -2.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    0.4377   -2.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351   -0.3146   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -1.4445   -1.0054 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    0.3010   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210    1.5688   -1.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    1.8989   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    3.1676   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    3.4036   -0.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213    4.1773   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    5.4226   -2.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699    0.7699   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202   -0.2274   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.3910    0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -1.0873    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -2.1388    1.6266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -3.1074    1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -4.3903    2.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -5.2717    1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -4.8228    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593   -5.8690    1.0793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -3.5312    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861   -2.6819    0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672    0.2839    0.5742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0872    1.1450    1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5082    0.9500    1.9536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982    0.9673    3.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0433    0.7212    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310    0.8306    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6064    0.5444   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998    0.1451   -2.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2270   -3.7332 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    0.0450   -1.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.3228   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6902   -1.2396   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516    0.3987   -3.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4765    0.0551   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6214    2.1994   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    6.1792   -2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459    5.7408   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    5.3080   -2.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807   -2.1604    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -4.7340    2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -6.2784    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -3.2405    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5206    0.6825    2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.1775    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    1.8965    3.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064    0.1211    3.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    0.9375    4.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177    1.1436    0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    0.6360   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -0.2742   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  1
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 13  5  2  0
 23 14  1  0
 34 24  1  0
 24 12  1  0
 34 28  1  0
 23 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 22 45  1  0
 25 46  1  0
 25 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 29 51  1  0
 30 52  1  0
 33 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       5.783  -0.147  -2.412  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.548   0.438  -2.069  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.635  -0.315  -1.304  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.028  -1.444  -1.005  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.366   0.301  -0.958  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.021   1.569  -1.337  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.813   1.899  -0.898  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.108   3.168  -1.115  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.039   3.404  -0.674  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.721   4.177  -1.844  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.045   5.423  -2.064  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.370   0.770  -0.198  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.320  -0.227  -0.228  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.823  -1.391   0.493  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.429  -1.087   0.956  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.952  -2.139   1.627  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.047  -3.107   1.597  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.061  -4.390   2.124  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.987  -5.272   1.992  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.082  -4.823   1.298  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       3.459  -5.869   1.079  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       2.131  -3.531   0.751  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.086  -2.682   0.894  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.767   0.284   0.574  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.087   1.145   1.775  0.00  0.00           C+0
HETATM   26  N   UNK     0      -2.508   0.950   1.954  0.00  0.00           N+0
HETATM   27  C   UNK     0      -3.298   0.967   3.160  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.043   0.721   0.654  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.331   0.831   0.150  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.606   0.544  -1.188  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.600   0.145  -2.043  0.00  0.00           C+0
HETATM   32 Cl   UNK     0      -3.890  -0.227  -3.733  0.00  0.00          Cl+0
HETATM   33  C   UNK     0      -2.330   0.045  -1.515  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.041   0.323  -0.200  0.00  0.00           C+0
HETATM   35  H   UNK     0       5.690  -1.240  -2.615  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.152   0.399  -3.324  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.476   0.055  -1.564  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.621   2.199  -1.898  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.806   6.179  -2.350  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.346   5.741  -1.056  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.756   5.308  -2.805  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.881  -2.160   2.069  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.928  -4.734   2.669  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.961  -6.278   2.413  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.003  -3.240   0.226  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.521   0.683   2.624  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.768   2.178   1.715  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.896   1.897   3.262  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.006   0.121   3.220  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.637   0.938   4.064  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.118   1.144   0.822  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.607   0.636  -1.554  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.545  -0.274  -2.212  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   38                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   39   40   41                                             
CONECT   12    7   13   24                                                  
CONECT   13   12   14    5                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   42                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   44                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   45                                                  
CONECT   23   22   14   17                                                  
CONECT   24   15   25   34   12                                             
CONECT   25   24   26   46   47                                             
CONECT   26   25   27   28                                                  
CONECT   27   26   48   49   50                                             
CONECT   28   26   29   34                                                  
CONECT   29   28   30   51                                                  
CONECT   30   29   31   52                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   53                                                  
CONECT   34   33   24   28                                                  
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    6                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   16                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   22                                                            
CONECT   46   25                                                            
CONECT   47   25                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   33                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

RDKit          3D

53 58  0  0  0  0  0  0  0  0999 V2000
    5.7833   -0.1468   -2.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    0.4377   -2.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351   -0.3146   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -1.4445   -1.0054 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    0.3010   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210    1.5688   -1.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8134    1.8989   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    3.1676   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    3.4036   -0.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213    4.1773   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    5.4226   -2.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699    0.7699   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202   -0.2274   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.3910    0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -1.0873    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -2.1388    1.6266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -3.1074    1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -4.3903    2.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -5.2717    1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -4.8228    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4593   -5.8690    1.0793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -3.5312    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861   -2.6819    0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672    0.2839    0.5742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0872    1.1450    1.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5082    0.9500    1.9536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982    0.9673    3.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0433    0.7212    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310    0.8306    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6064    0.5444   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5998    0.1451   -2.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2270   -3.7332 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    0.0450   -1.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.3228   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6902   -1.2396   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516    0.3987   -3.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4765    0.0551   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6214    2.1994   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    6.1792   -2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459    5.7408   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    5.3080   -2.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8807   -2.1604    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -4.7340    2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -6.2784    2.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -3.2405    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5206    0.6825    2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.1775    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    1.8965    3.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064    0.1211    3.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    0.9375    4.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1177    1.1436    0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    0.6360   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453   -0.2742   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  1
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 13  5  2  0
 23 14  1  0
 34 24  1  0
 24 12  1  0
 34 28  1  0
 23 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 22 45  1  0
 25 46  1  0
 25 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 29 51  1  0
 30 52  1  0
 33 53  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
12',14'-Dimethyl (3R)-4',5-dichloro-1-methyl-1,2-dihydro-8',13'-diazaspiro[indole-3,10'-tetracyclo[7.6.0.0,.0,]pentadecane]-1'(9'),2'(7'),3',5',11',14'-hexaene-12',14'-dicarboxylic acid	Generator

Chemical Formula

C₂₅H₁₉Cl₂N₃O₄

Average Mass

496.3400 Da

Monoisotopic Mass

495.07526 Da

IUPAC Name

12',14'-dimethyl (3R)-4',5-dichloro-1-methyl-1,2-dihydro-8',13'-diazaspiro[indole-3,10'-tetracyclo[7.6.0.0^{2,7}.0^{11,15}]pentadecane]-1'(9'),2',4',6',11',14'-hexaene-12',14'-dicarboxylate

Traditional Name

12',14'-dimethyl (3R)-4',5-dichloro-1-methyl-2H-8',13'-diazaspiro[indole-3,10'-tetracyclo[7.6.0.0^{2,7}.0^{11,15}]pentadecane]-1'(9'),2',4',6',11',14'-hexaene-12',14'-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C3=C(NC4=C3C=C(Cl)C=C4)[C@@]3(CN(C)C4=C3C=C(Cl)C=C4)C2=C(N1)C(=O)OC

InChI Identifier

InChI=1S/C25H19Cl2N3O4/c1-30-10-25(14-9-12(27)5-7-16(14)30)19-18(20(23(31)33-2)29-21(19)24(32)34-3)17-13-8-11(26)4-6-15(13)28-22(17)25/h4-9,28-29H,10H2,1-3H3/t25-/m1/s1

InChI Key

HNJSPDJKLKPYKX-RUZDIDTESA-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
Streptomyces	NPAtlas	22694269

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Pyrrole-2-carboxylic acid or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
Aryl chloride
Aryl halide
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Methyl ester
Heteroaromatic compound
Pyrrole
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
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	5.16	ALOGPS
logP	4.96	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.95 m³·mol⁻¹	ChemAxon
Polarizability	51.82 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA010494

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29214711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60166300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang W, Liu Z, Li S, Yang T, Zhang Q, Ma L, Tian X, Zhang H, Huang C, Zhang S, Ju J, Shen Y, Zhang C: Spiroindimicins A-D: new bisindole alkaloids from a deep-sea-derived actinomycete. Org Lett. 2012 Jul 6;14(13):3364-7. doi: 10.1021/ol301343n. Epub 2012 Jun 13. [PubMed:22694269 ]
Zhang Z, Ray S, Imlay L, Callaghan LT, Niederstrasser H, Mallipeddi PL, Posner BA, Wetzel DM, Phillips MA, Smith MW: Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity. Chem Sci. 2021 Jun 30;12(30):10388-10394. doi: 10.1039/d1sc02838c. eCollection 2021 Aug 4. [PubMed:34377425 ]

Showing NP-Card for Spiroindimicin D (NP0010871)

MOL for NP0010871 (Spiroindimicin D)

3D MOL for NP0010871 (Spiroindimicin D)

3D SDF for NP0010871 (Spiroindimicin D)

3D-SDF for NP0010871 (Spiroindimicin D)

PDB for NP0010871 (Spiroindimicin D)

3D PDB for NP0010871 (Spiroindimicin D)

SMILES for NP0010871 (Spiroindimicin D)

INCHI for NP0010871 (Spiroindimicin D)

Structure for NP0010871 (Spiroindimicin D)

3D Structure for NP0010871 (Spiroindimicin D)