NP-MRD: Showing NP-Card for Duocarmycin C2 (NP0021086)

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Record Information

Version

1.0

Created at

2021-01-06 06:22:51 UTC

Updated at

2021-07-15 17:35:25 UTC

NP-MRD ID

NP0021086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Duocarmycin C2

Provided By

NPAtlas

Description

Duocarmycin C2 is found in Streptomyces sp. It was first documented in 1988 (PMID: 3255306). Based on a literature review very few articles have been published on methyl 8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate (PMID: 34383398) (PMID: 34383397) (PMID: 34383396) (PMID: 34384147).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120403D          

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     RDKit          3D

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M  END


  Mrv1652306242120403D          

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    2.0471   -0.0495   -1.5403 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5551    1.3247   -1.9271 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5754    1.8457   -3.3430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6245    0.1448   -1.0566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5460   -0.4361    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2210   -1.7917    2.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.0750    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502   -0.4028    1.4791 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4919    3.0850    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2227    2.8675    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743    3.5832   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -1.8502   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -2.0951   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1532   -0.5465   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5129   -2.4280    1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349   -2.4749    3.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.5469    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.6665   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.3537   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    2.0390   -1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -0.4915   -1.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    1.2060   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    0.7681   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    1.6015   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3312    1.4979   -3.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5354    2.8191   -3.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8324    3.0421   -2.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1489   -0.9144   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2494   -1.7754    3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3256   -2.3329    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -0.8655    2.4052 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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 37 38  1  0  0  0  0
 15  5  1  0  0  0  0
 38 24  1  0  0  0  0
 14  8  1  0  0  0  0
 37 26  1  0  0  0  0
 21 12  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
  7 45  1  0  0  0  0
 10 46  1  0  0  0  0
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 36 61  1  0  0  0  0
 36 62  1  0  0  0  0
 36 63  1  0  0  0  0
 38 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2N([H])[C@](C(=O)OC([H])([H])[H])(C(=O)C2=C2C(=C1[H])N(C(=O)C1=C([H])C3=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C3N1[H])C([H])([H])[C@@]2([H])C([H])([H])Cl)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H26ClN3O8/c1-26(25(34)38-5)23(32)18-17-12(9-27)10-30(14(17)8-15(31)20(18)29-26)24(33)13-6-11-7-16(35-2)21(36-3)22(37-4)19(11)28-13/h6-8,12,28-29,31H,9-10H2,1-5H3/t12-,26+/m1/s1

> <INCHI_KEY>
BOGFADYROAVVTF-UHFFFAOYSA-N

> <FORMULA>
C26H26ClN3O8

> <MOLECULAR_WEIGHT>
543.96

> <EXACT_MASS>
543.1408425

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
56.15614320525464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
2.4904446293333335

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.23865135101255

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.151541904271662

> <JCHEM_PKA_STRONGEST_BASIC>
-2.124909297397335

> <JCHEM_POLAR_SURFACE_AREA>
139.42000000000002

> <JCHEM_REFRACTIVITY>
139.20399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    7.1920    2.8278   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0232    1.5125   -0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6591   -1.3784   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -1.7374    0.7839 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -1.4976    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -1.6993    1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -2.2279    3.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -1.3710    1.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -0.8298    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -0.6316   -0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877   -0.9636   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -0.8695   -1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.8078   -2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471   -0.0495   -1.5403 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.5754    1.8457   -3.3430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6245    0.1448   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.4361    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963   -0.6115    1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -1.1902    2.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -0.2030    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    0.4292   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058    0.6096   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7510    1.1799   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0653    1.2113   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0566    1.7761   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5820   -0.3880    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940    0.0991    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8406   -0.4444    2.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2210   -1.7917    2.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.0750    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502   -0.4028    1.4791 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4919    3.0850    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2227    2.8675    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743    3.5832   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -1.8502   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -2.0951   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1532   -0.5465   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5129   -2.4280    1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349   -2.4749    3.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.5469    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.6665   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.3537   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    2.0390   -1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -0.4915   -1.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    1.2060   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    0.7681   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    1.6015   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8324    3.0421   -2.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1489   -0.9144   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7198   -1.1054    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5785   -0.0186    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5841   -2.3296    3.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2494   -1.7754    3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3256   -2.3329    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -0.8655    2.4052 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
  5  3  1  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 15  5  1  0
 38 24  1  0
 14  8  1  0
 37 26  1  0
 21 12  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  6 43  1  0
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  7 45  1  0
 10 46  1  0
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 33 60  1  0
 36 61  1  0
 36 62  1  0
 36 63  1  0
 38 64  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       7.192   2.828  -0.102  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.023   1.513  -0.591  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.602   0.497   0.261  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.364   0.717   1.472  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.433  -0.864  -0.269  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.659  -1.378  -0.983  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.995  -1.737   0.784  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.585  -1.498   0.933  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.704  -1.699   1.972  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.168  -2.228   3.151  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.373  -1.371   1.821  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.855  -0.830   0.638  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.741  -0.632  -0.393  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.088  -0.964  -0.242  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.236  -0.870  -1.155  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.240  -0.808  -2.389  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.047  -0.050  -1.540  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.555   1.325  -1.927  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.575   1.846  -3.343  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       0.625   0.145  -1.057  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.546  -0.436   0.250  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.596  -0.612   1.031  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.450  -1.190   2.174  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.959  -0.203   0.685  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.429   0.429  -0.425  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.806   0.610  -0.297  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.751   1.180  -1.111  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.065   1.211  -0.705  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.057   1.776  -1.491  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.685   2.327  -2.737  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.440   0.674   0.517  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.770   0.724   0.891  0.00  0.00           O+0
HETATM   33  C   UNK     0      -8.582  -0.388   0.502  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.494   0.099   1.339  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.841  -0.444   2.561  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.221  -1.792   2.739  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.154   0.075   0.908  0.00  0.00           C+0
HETATM   38  N   UNK     0      -3.050  -0.403   1.479  0.00  0.00           N+0
HETATM   39  H   UNK     0       6.492   3.085   0.702  0.00  0.00           H+0
HETATM   40  H   UNK     0       8.223   2.868   0.351  0.00  0.00           H+0
HETATM   41  H   UNK     0       7.174   3.583  -0.897  0.00  0.00           H+0
HETATM   42  H   UNK     0       8.381  -1.850  -0.286  0.00  0.00           H+0
HETATM   43  H   UNK     0       7.321  -2.095  -1.742  0.00  0.00           H+0
HETATM   44  H   UNK     0       8.153  -0.547  -1.510  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.513  -2.428   1.370  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.135  -2.475   3.284  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.727  -1.547   2.664  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.069  -0.667  -2.442  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.597   1.354  -2.252  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.325   2.039  -1.102  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.036  -0.492  -1.718  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.338   1.206  -1.087  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.897   0.768  -1.297  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.442   1.601  -2.074  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.331   1.498  -3.398  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.535   2.819  -3.248  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.832   3.042  -2.634  0.00  0.00           H+0
HETATM   58  H   UNK     0      -8.149  -0.914  -0.378  0.00  0.00           H+0
HETATM   59  H   UNK     0      -8.720  -1.105   1.329  0.00  0.00           H+0
HETATM   60  H   UNK     0      -9.579  -0.019   0.169  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.584  -2.330   3.473  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.249  -1.775   3.188  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.326  -2.333   1.781  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.025  -0.866   2.405  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   15                                             
CONECT    6    5   42   43   44                                             
CONECT    7    5    8   45                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   46                                                       
CONECT   11    9   12   47                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15    8                                                  
CONECT   15   14   16    5                                                  
CONECT   16   15                                                            
CONECT   17   13   18   20   48                                             
CONECT   18   17   19   49   50                                             
CONECT   19   18                                                            
CONECT   20   17   21   51   52                                             
CONECT   21   20   22   12                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   38                                                  
CONECT   25   24   26   53                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28   54                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   55   56   57                                             
CONECT   31   28   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   58   59   60                                             
CONECT   34   31   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   61   62   63                                             
CONECT   37   34   38   26                                                  
CONECT   38   37   24   64                                                  
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   25                                                            
CONECT   54   27                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
CONECT   58   33                                                            
CONECT   59   33                                                            
CONECT   60   33                                                            
CONECT   61   36                                                            
CONECT   62   36                                                            
CONECT   63   36                                                            
CONECT   64   38                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

RDKit          3D

64 68  0  0  0  0  0  0  0  0999 V2000
    7.1920    2.8278   -0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0232    1.5125   -0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6023    0.4966    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3638    0.7171    1.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4332   -0.8641   -0.2694 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6591   -1.3784   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -1.7374    0.7839 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -1.4976    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -1.6993    1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -2.2279    3.1514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -1.3710    1.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -0.8298    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -0.6316   -0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877   -0.9636   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -0.8695   -1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398   -0.8078   -2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471   -0.0495   -1.5403 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5551    1.3247   -1.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754    1.8457   -3.3430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6245    0.1448   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.4361    0.2504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963   -0.6115    1.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -1.1902    2.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -0.2030    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    0.4292   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058    0.6096   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7510    1.1799   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0653    1.2113   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0566    1.7761   -1.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6847    2.3268   -2.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4404    0.6735    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    0.7237    0.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5820   -0.3880    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940    0.0991    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8406   -0.4444    2.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2210   -1.7917    2.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.0750    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502   -0.4028    1.4791 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4919    3.0850    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2227    2.8675    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743    3.5832   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -1.8502   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -2.0951   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1532   -0.5465   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5129   -2.4280    1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349   -2.4749    3.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -1.5469    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -0.6665   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    1.3537   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    2.0390   -1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -0.4915   -1.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    1.2060   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965    0.7681   -1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    1.6015   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3312    1.4979   -3.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5354    2.8191   -3.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8324    3.0421   -2.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1489   -0.9144   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7198   -1.1054    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5785   -0.0186    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5841   -2.3296    3.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2494   -1.7754    3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3256   -2.3329    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -0.8655    2.4052 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
  5  3  1  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 15  5  1  0
 38 24  1  0
 14  8  1  0
 37 26  1  0
 21 12  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
 10 46  1  0
 11 47  1  0
 17 48  1  6
 18 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 25 53  1  0
 27 54  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
 33 58  1  0
 33 59  1  0
 33 60  1  0
 36 61  1  0
 36 62  1  0
 36 63  1  0
 38 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylic acid	Generator

Chemical Formula

C₂₆H₂₆ClN₃O₈

Average Mass

543.9600 Da

Monoisotopic Mass

543.14084 Da

IUPAC Name

methyl (2S,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1H,2H,3H,6H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

Traditional Name

methyl (2S,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3H,7H,8H-pyrrolo[3,2-e]indole-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)NC2=C(O)C=C3N(CC(CCl)C3=C2C1=O)C(=O)C1=CC2=CC(OC)=C(OC)C(OC)=C2N1

InChI Identifier

InChI=1S/C26H26ClN3O8/c1-26(25(34)38-5)23(32)18-17-12(9-27)10-30(14(17)8-15(31)20(18)29-26)24(33)13-6-11-7-16(35-2)21(36-3)22(37-4)19(11)28-13/h6-8,12,28-29,31H,9-10H2,1-5H3

InChI Key

BOGFADYROAVVTF-UHFFFAOYSA-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 sp.	NPAtlas	3255306

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.46	ALOGPS
logP	2.49	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.42 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.2 m³·mol⁻¹	ChemAxon
Polarizability	56.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA000737

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8657915

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10482508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yasuzawa T, Iida T, Muroi K, Ichimura M, Takahashi K, Sano H: Structures of duocarmycins, novel antitumor antibiotics produced by Streptomyces sp. Chem Pharm Bull (Tokyo). 1988 Sep;36(9):3728-31. doi: 10.1248/cpb.36.3728. [PubMed:3255306 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
Authors unspecified: Ponesimod. 2012. [PubMed:34383396 ]
Lee J, Cho Y, Choi KH, Hwang I, Oh YL: Metastatic leiomyosarcoma of the thyroid gland: cytologic findings and differential diagnosis. J Pathol Transl Med. 2021 Aug 13. pii: jptm.2021.06.23. doi: 10.4132/jptm.2021.06.23. [PubMed:34384147 ]

Showing NP-Card for Duocarmycin C2 (NP0021086)

MOL for NP0021086 (Duocarmycin C2)

3D MOL for NP0021086 (Duocarmycin C2)

3D SDF for NP0021086 (Duocarmycin C2)

3D-SDF for NP0021086 (Duocarmycin C2)

PDB for NP0021086 (Duocarmycin C2)

3D PDB for NP0021086 (Duocarmycin C2)

SMILES for NP0021086 (Duocarmycin C2)

INCHI for NP0021086 (Duocarmycin C2)

Structure for NP0021086 (Duocarmycin C2)

3D Structure for NP0021086 (Duocarmycin C2)