NP-MRD: Showing NP-Card for Duocarmycin SA (NP0008521)

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Record Information

Version

1.0

Created at

2020-12-09 06:05:25 UTC

Updated at

2021-07-15 17:00:40 UTC

NP-MRD ID

NP0008521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Duocarmycin SA

Provided By

NPAtlas

Description

Duocarmycin sa belongs to the class of organic compounds known as indolecarboxamides and derivatives. Indolecarboxamides and derivatives are compounds containing a carboxamide group attached to an indole. Duocarmycin SA is found in Streptomyces sp. It was first documented in 1991 (PMID: 1955385). Based on a literature review very few articles have been published on duocarmycin sa.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106103D          

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     RDKit          3D

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M  END


  Mrv1652306242106103D          

 58 63  0  0  0  0            999 V2000
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    0.9625    0.3352   -0.7528 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4014    0.8958   -0.5992 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5538    1.4678    0.8152 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0921    0.1306    0.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4380    1.6087   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457    2.4620    1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8308    3.3125    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5862    1.7634    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921   -1.9499    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890   -3.0848    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949   -2.2752    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4701   -1.9445    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -2.6986    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9710   -1.8551    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4374   -1.3218    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    2.4043   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8757    2.8918   -2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4104    2.0865   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.7593   -4.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5462    0.0323   -3.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931    0.6272   -3.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    0.3764   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.1659   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.0460   -1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    1.5012   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.2688    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190    1.4498    1.5165 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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
  9  5  1  0  0  0  0
 35 13  1  0  0  0  0
 35  7  1  0  0  0  0
 31 17  1  0  0  0  0
 35 33  1  0  0  0  0
 30 19  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  6 39  1  0  0  0  0
  9 40  1  0  0  0  0
 12 41  1  0  0  0  0
 18 42  1  0  0  0  0
 20 43  1  0  0  0  0
 23 44  1  0  0  0  0
 23 45  1  0  0  0  0
 23 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 29 50  1  0  0  0  0
 29 51  1  0  0  0  0
 29 52  1  0  0  0  0
 31 53  1  0  0  0  0
 32 54  1  0  0  0  0
 32 55  1  0  0  0  0
 33 56  1  6  0  0  0
 34 57  1  0  0  0  0
 34 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=C([H])C2=C1C(=O)C([H])=C1N(C(=O)C3=C([H])C4=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C4N3[H])C([H])([H])[C@@]3([H])C([H])([H])[C@@]213)C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H23N3O7/c1-32-17-6-11-5-14(26-19(11)22(34-3)21(17)33-2)23(30)28-10-12-9-25(12)13-7-15(24(31)35-4)27-20(13)16(29)8-18(25)28/h5-8,12,26-27H,9-10H2,1-4H3/t12-,25-/m1/s1

> <INCHI_KEY>
VQNATVDKACXKTF-XELLLNAOSA-N

> <FORMULA>
C25H23N3O7

> <MOLECULAR_WEIGHT>
477.473

> <EXACT_MASS>
477.153600093

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
50.70148177995524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.0^{1,12}.0^{2,6}]trideca-2(6),3,8-triene-4-carboxylate

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
0.9069416906666671

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.661795921390603

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.5210276060537

> <JCHEM_PKA_STRONGEST_BASIC>
-4.354796630106123

> <JCHEM_POLAR_SURFACE_AREA>
122.95

> <JCHEM_REFRACTIVITY>
126.23399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.0^{1,12}.0^{2,6}]trideca-2(6),3,8-triene-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
    9.7644    2.3076    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4201    1.8653    0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1256    0.5841    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0352   -0.2009    1.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7554    0.0492    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    0.7286    0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103   -0.1019    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077   -1.3071    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3496   -1.1819    1.2063 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -2.4521    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269   -3.5648    1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -2.2556    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -1.0862    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977   -0.7226    0.2252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627   -1.2996    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -2.1892    1.6926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461   -1.0169    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7461   -1.5737    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729   -1.0601    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2192   -1.2523    0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -0.6098    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5243   -0.8334    0.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8888   -1.7237    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804    0.2535   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7683    0.8917   -1.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3366    2.1246   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559    0.4576   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606    1.3279   -2.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592    0.8843   -3.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963   -0.2022   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -0.2040   -0.5001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625    0.3352   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014    0.8958   -0.5992 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5538    1.4678    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921    0.1306    0.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4380    1.6087   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457    2.4620    1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8308    3.3125    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5862    1.7634    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921   -1.9499    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890   -3.0848    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949   -2.2752    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4701   -1.9445    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -2.6986    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9710   -1.8551    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4374   -1.3218    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    2.4043   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8757    2.8918   -2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4104    2.0865   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.7593   -4.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5462    0.0323   -3.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931    0.6272   -3.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    0.3764   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.1659   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.0460   -1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    1.5012   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.2688    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190    1.4498    1.5165 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 30 31  1  0
 14 32  1  0
 32 33  1  0
 33 34  1  0
 35 34  1  1
  9  5  1  0
 35 13  1  0
 35  7  1  0
 31 17  1  0
 35 33  1  0
 30 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  6 39  1  0
  9 40  1  0
 12 41  1  0
 18 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
 26 47  1  0
 26 48  1  0
 26 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 31 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  6
 34 57  1  0
 34 58  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       9.764   2.308   0.516  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.420   1.865   0.486  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.126   0.584   0.863  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.035  -0.201   1.233  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.755   0.049   0.860  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.601   0.729   0.493  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.510  -0.102   0.622  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.008  -1.307   1.074  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.350  -1.182   1.206  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.121  -2.452   1.286  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.527  -3.565   1.697  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.706  -2.256   0.997  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.261  -1.086   0.570  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.898  -0.723   0.225  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.263  -1.300   0.775  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.083  -2.189   1.693  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.646  -1.017   0.432  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.746  -1.574   1.090  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.873  -1.060   0.513  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.219  -1.252   0.755  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.186  -0.610   0.027  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.524  -0.833   0.305  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.889  -1.724   1.338  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.780   0.254  -0.975  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.768   0.892  -1.697  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.337   2.125  -1.377  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.456   0.458  -1.230  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.061   1.328  -2.240  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.859   0.884  -3.575  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.496  -0.202  -0.483  0.00  0.00           C+0
HETATM   31  N   UNK     0      -2.164  -0.204  -0.500  0.00  0.00           N+0
HETATM   32  C   UNK     0       0.963   0.335  -0.753  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.401   0.896  -0.599  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.554   1.468   0.815  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.092   0.131   0.409  0.00  0.00           C+0
HETATM   36  H   UNK     0      10.438   1.609  -0.022  0.00  0.00           H+0
HETATM   37  H   UNK     0      10.046   2.462   1.569  0.00  0.00           H+0
HETATM   38  H   UNK     0       9.831   3.313   0.008  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.586   1.763   0.156  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.992  -1.950   1.537  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.989  -3.085   1.133  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.695  -2.275   1.899  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.470  -1.944   1.557  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.354  -2.699   1.153  0.00  0.00           H+0
HETATM   45  H   UNK     0      -8.971  -1.855   1.403  0.00  0.00           H+0
HETATM   46  H   UNK     0      -7.437  -1.322   2.280  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.292   2.404  -0.324  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.876   2.892  -2.048  0.00  0.00           H+0
HETATM   49  H   UNK     0      -8.410   2.087  -1.675  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.078   1.759  -4.228  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.546   0.032  -3.785  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.793   0.627  -3.739  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.644   0.376  -1.204  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.264   1.166  -0.463  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.864  -0.046  -1.751  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.816   1.501  -1.400  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.281   2.269   0.986  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.719   1.450   1.517  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7   39                                                  
CONECT    7    6    8   35                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5   40                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   41                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   31                                                  
CONECT   18   17   19   42                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21   43                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   44   45   46                                             
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   47   48   49                                             
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   50   51   52                                             
CONECT   30   27   31   19                                                  
CONECT   31   30   17   53                                                  
CONECT   32   14   33   54   55                                             
CONECT   33   32   34   35   56                                             
CONECT   34   33   35   57   58                                             
CONECT   35   34   13    7   33                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    6                                                            
CONECT   40    9                                                            
CONECT   41   12                                                            
CONECT   42   18                                                            
CONECT   43   20                                                            
CONECT   44   23                                                            
CONECT   45   23                                                            
CONECT   46   23                                                            
CONECT   47   26                                                            
CONECT   48   26                                                            
CONECT   49   26                                                            
CONECT   50   29                                                            
CONECT   51   29                                                            
CONECT   52   29                                                            
CONECT   53   31                                                            
CONECT   54   32                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   34                                                            
CONECT   58   34                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

RDKit          3D

58 63  0  0  0  0  0  0  0  0999 V2000
    9.7644    2.3076    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4201    1.8653    0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1256    0.5841    0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0352   -0.2009    1.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7554    0.0492    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009    0.7286    0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103   -0.1019    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077   -1.3071    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3496   -1.1819    1.2063 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -2.4521    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5269   -3.5648    1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -2.2556    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2606   -1.0862    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977   -0.7226    0.2252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627   -1.2996    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -2.1892    1.6926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461   -1.0169    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7461   -1.5737    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729   -1.0601    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2192   -1.2523    0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -0.6098    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5243   -0.8334    0.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8888   -1.7237    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804    0.2535   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7683    0.8917   -1.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3366    2.1246   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559    0.4576   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606    1.3279   -2.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8592    0.8843   -3.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963   -0.2022   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -0.2040   -0.5001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625    0.3352   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014    0.8958   -0.5992 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5538    1.4678    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921    0.1306    0.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4380    1.6087   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457    2.4620    1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8308    3.3125    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5862    1.7634    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921   -1.9499    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890   -3.0848    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949   -2.2752    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4701   -1.9445    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -2.6986    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9710   -1.8551    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4374   -1.3218    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    2.4043   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8757    2.8918   -2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4104    2.0865   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.7593   -4.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5462    0.0323   -3.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931    0.6272   -3.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    0.3764   -1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.1659   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635   -0.0460   -1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    1.5012   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.2688    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190    1.4498    1.5165 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 30 31  1  0
 14 32  1  0
 32 33  1  0
 33 34  1  0
 35 34  1  1
  9  5  1  0
 35 13  1  0
 35  7  1  0
 31 17  1  0
 35 33  1  0
 30 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  6 39  1  0
  9 40  1  0
 12 41  1  0
 18 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
 26 47  1  0
 26 48  1  0
 26 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 31 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  6
 34 57  1  0
 34 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(+)-Duocarmycin sa	MeSH
Methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.0,.0,]trideca-2(6),3,8-triene-4-carboxylic acid	Generator

Chemical Formula

C₂₅H₂₃N₃O₇

Average Mass

477.4730 Da

Monoisotopic Mass

477.15360 Da

IUPAC Name

methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.0^{1,12}.0^{2,6}]trideca-2(6),3,8-triene-4-carboxylate

Traditional Name

methyl (1R,12S)-7-oxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.0^{1,12}.0^{2,6}]trideca-2(6),3,8-triene-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=C(N1)C(=O)C=C1N(C[C@H]3C[C@@]213)C(=O)C1=CC2=CC(OC)=C(OC)C(OC)=C2N1

InChI Identifier

InChI=1S/C25H23N3O7/c1-32-17-6-11-5-14(26-19(11)22(34-3)21(17)33-2)23(30)28-10-12-9-25(12)13-7-15(24(31)35-4)27-20(13)16(29)8-18(25)28/h5-8,12,26-27H,9-10H2,1-4H3/t12-,25-/m1/s1

InChI Key

VQNATVDKACXKTF-XELLLNAOSA-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	1955385

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. DO113 (FERM BP-222)	KNApSAcK Database	22123792
Streptomyces sp.DO-113	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxamides and derivatives. Indolecarboxamides and derivatives are compounds containing a carboxamide group attached to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxamides and derivatives

Alternative Parents

Substituents

Indolecarboxamide derivative
Indole
N-acyl-piperidine
Anisole
2-heteroaryl carboxamide
N-acylpyrrolidine
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aryl ketone
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Piperidine
Methyl ester
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Heteroaromatic compound
Vinylogous amide
Carboxylic acid ester
Carboxamide group
Ketone
Carboxylic acid derivative
Azacycle
Ether
Monocarboxylic acid or derivatives
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
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	2.88	ALOGPS
logP	0.91	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.23 m³·mol⁻¹	ChemAxon
Polarizability	50.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA013520

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017024

Chemspider ID

103203

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115369

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ichimura M, Ogawa T, Katsumata S, Takahashi K, Takahashi I, Nakano H: Duocarmycins, new antitumor antibiotics produced by Streptomyces; producing organisms and improved production. J Antibiot (Tokyo). 1991 Oct;44(10):1045-53. doi: 10.7164/antibiotics.44.1045. [PubMed:1955385 ]

Showing NP-Card for Duocarmycin SA (NP0008521)

MOL for NP0008521 (Duocarmycin SA)

3D MOL for NP0008521 (Duocarmycin SA)

3D SDF for NP0008521 (Duocarmycin SA)

3D-SDF for NP0008521 (Duocarmycin SA)

PDB for NP0008521 (Duocarmycin SA)

3D PDB for NP0008521 (Duocarmycin SA)

SMILES for NP0008521 (Duocarmycin SA)

INCHI for NP0008521 (Duocarmycin SA)

Structure for NP0008521 (Duocarmycin SA)

3D Structure for NP0008521 (Duocarmycin SA)