NP-MRD: Showing NP-Card for Indocarbazostatin B (NP0004201)

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Record Information

Version

2.0

Created at

2020-12-09 01:41:23 UTC

Updated at

2021-07-15 16:48:31 UTC

NP-MRD ID

NP0004201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indocarbazostatin B

Provided By

NPAtlas

Description

Ethyl (15S,16S,18R)-9-amino-3,10,16-trihydroxy-15-methyl-5-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1¹⁵,¹⁸.0²,⁶.0⁷,²⁷.0⁸,¹³.0¹⁹,²⁶.0²⁰,²⁵]Octacosa-1,3,6,8(13),9,11,20,22,24,26-decaene-16-carboxylate belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. Indocarbazostatin B is found in Streptomyces sp. Indocarbazostatin B was first documented in 2002 (PMID: 12061542). Based on a literature review very few articles have been published on ethyl (15S,16S,18R)-9-amino-3,10,16-trihydroxy-15-methyl-5-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1¹⁵,¹⁸.0²,⁶.0⁷,²⁷.0⁸,¹³.0¹⁹,²⁶.0²⁰,²⁵]Octacosa-1,3,6,8(13),9,11,20,22,24,26-decaene-16-carboxylate (PMID: 15638322) (PMID: 16506693) (PMID: 12061543).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118053D          

 61 68  0  0  0  0            999 V2000
    5.7409    1.5213   -2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    1.4446   -2.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.6166    0.1570   -0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5775   -1.3585    0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1148   -1.6403    1.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  8  9  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118053D          

 61 68  0  0  0  0            999 V2000
    5.7409    1.5213   -2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    1.4446   -2.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.6774   -1.4526   -0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886    0.8555   -0.4413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614    1.7187   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    2.9208   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0902    2.5262   -2.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    0.7578   -3.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935    1.2057   -1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718    2.4477   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108    1.1355   -3.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -2.1898    0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -2.8070   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -1.7002   -1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -3.5702    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -0.6756    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540    0.8583    2.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    0.4804    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.3630    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    4.7296    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    6.2531    0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606    4.3440   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 24 25  2  0  0  0  0
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 26 27  2  0  0  0  0
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 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
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 11  6  1  0  0  0  0
 34 13  1  0  0  0  0
 32  9  1  0  0  0  0
 21 14  1  0  0  0  0
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  1 40  1  0  0  0  0
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  2 43  1  0  0  0  0
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 28 58  1  0  0  0  0
 29 59  1  0  0  0  0
 30 60  1  0  0  0  0
 37 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2N3C4=C5N(C6=C([H])C([H])=C([H])C([H])=C6C5=C5C(=O)N([H])C(=O)C5=C4C2=C1N([H])[H])[C@]1([H])O[C@@]3(C([H])([H])[H])[C@](O[H])(C(=O)OC([H])([H])C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H22N4O7/c1-3-38-26(36)28(37)10-15-31-12-7-5-4-6-11(12)16-19-20(25(35)30-24(19)34)18-17-13(8-9-14(33)21(17)29)32(23(18)22(16)31)27(28,2)39-15/h4-9,15,33,37H,3,10,29H2,1-2H3,(H,30,34,35)/t15-,27+,28-/m1/s1

> <INCHI_KEY>
VEXMHCAEEISMPG-ZXOINBKBSA-N

> <FORMULA>
C28H22N4O7

> <MOLECULAR_WEIGHT>
526.505

> <EXACT_MASS>
526.148849064

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
53.79602558432617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (15S,16S,18R)-9-amino-10,16-dihydroxy-15-methyl-3,5-dioxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1,6,8,10,12,20,22,24,26-nonaene-16-carboxylate

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.602157759

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.769232817513828

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.986406917851182

> <JCHEM_PKA_STRONGEST_BASIC>
1.8723319087470423

> <JCHEM_POLAR_SURFACE_AREA>
158.04

> <JCHEM_REFRACTIVITY>
138.2768

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (15S,16S,18R)-9-amino-10,16-dihydroxy-15-methyl-3,5-dioxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1,6,8,10,12,20,22,24,26-nonaene-16-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 68  0  0  0  0  0  0  0  0999 V2000
    5.7409    1.5213   -2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0315    0.8616    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -0.4725   -0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5571   -2.4063    0.4631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536   -1.2595    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8331    0.0239    0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8672   -0.4963   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6774   -1.4526   -0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886    0.8555   -0.4413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614    1.7187   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    2.9208   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8108    1.1355   -3.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3372   -2.8070   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -1.7002   -1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -3.5702    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -0.6756    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540    0.8583    2.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    0.4804    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.3630    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    4.7296    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2263   -5.7336   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419   -6.6863   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081   -5.1328    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2762    1.1636   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
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 25 26  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 24 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 38 39  2  0
 11  6  1  0
 34 13  1  0
 32  9  1  0
 21 14  1  0
 34 22  1  0
 38 23  1  0
 33 25  1  0
 31 26  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  7 45  1  0
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  8 47  1  0
  9 48  1  1
 12 49  1  0
 12 50  1  0
 12 51  1  0
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 16 53  1  0
 18 54  1  0
 20 55  1  0
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 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 37 61  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       5.741   1.521  -2.365  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.213   1.445  -2.283  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.926   0.472  -1.294  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.617   0.157  -0.970  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.703   0.742  -1.562  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.372  -0.861   0.065  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.578  -1.359   0.568  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.613  -2.054  -0.465  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.881  -2.526   0.773  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.115  -1.640   1.768  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.558  -0.409   1.207  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.400   0.164   2.358  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.409   0.422   0.879  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.351   1.751   0.905  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.330   2.661   1.139  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.085   4.011   1.090  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.166   4.481   0.797  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.409   5.843   0.748  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.188   3.539   0.550  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.388   4.155   0.193  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.942   2.216   0.604  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.709   1.092   0.383  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.031   0.862   0.047  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.450  -0.473  -0.123  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.568  -1.514   0.042  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.632  -2.884  -0.081  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.660  -3.721  -0.404  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.397  -5.099  -0.453  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.148  -5.606  -0.188  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.107  -4.756   0.140  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.363  -3.413   0.188  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.557  -2.406   0.463  0.00  0.00           N+0
HETATM   33  C   UNK     0      -1.254  -1.260   0.385  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.833   0.024   0.557  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.867  -0.496  -0.432  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.677  -1.453  -0.665  0.00  0.00           O+0
HETATM   37  N   UNK     0      -5.289   0.856  -0.441  0.00  0.00           N+0
HETATM   38  C   UNK     0      -4.161   1.719  -0.144  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.380   2.921  -0.113  0.00  0.00           O+0
HETATM   40  H   UNK     0       6.090   2.526  -2.607  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.076   0.758  -3.123  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.194   1.206  -1.402  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.872   2.448  -2.015  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.811   1.135  -3.279  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.847  -2.190   0.078  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.337  -2.807  -0.836  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.940  -1.700  -1.261  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.113  -3.570   0.992  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.684  -0.676   3.091  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.854   0.858   2.994  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.399   0.480   2.001  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.322   2.363   1.343  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.892   4.730   1.284  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.297   6.253   0.541  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.661   4.344  -0.795  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.992   4.487   0.971  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.642  -3.382  -0.623  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.226  -5.734  -0.711  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.942  -6.686  -0.226  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.108  -5.133   0.355  0.00  0.00           H+0
HETATM   61  H   UNK     0      -6.276   1.164  -0.637  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3   43   44                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   11                                             
CONECT    7    6   45                                                       
CONECT    8    6    9   46   47                                             
CONECT    9    8   10   32   48                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13    6                                             
CONECT   12   11   49   50   51                                             
CONECT   13   11   14   34                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   52                                                  
CONECT   16   15   17   53                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   54                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19   55   56                                                  
CONECT   21   19   22   14                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   24   38                                                  
CONECT   24   23   25   35                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   57                                                  
CONECT   28   27   29   58                                                  
CONECT   29   28   30   59                                                  
CONECT   30   29   31   60                                                  
CONECT   31   30   32   26                                                  
CONECT   32   31   33    9                                                  
CONECT   33   32   34   25                                                  
CONECT   34   33   13   22                                                  
CONECT   35   24   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   61                                                  
CONECT   38   37   39   23                                                  
CONECT   39   38                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    2                                                            
CONECT   44    2                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   18                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   37                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

RDKit          3D

61 68  0  0  0  0  0  0  0  0999 V2000
    5.7409    1.5213   -2.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    1.4446   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9261    0.4719   -1.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166    0.1570   -0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028    0.7416   -1.5619 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -0.8606    0.0650 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5775   -1.3585    0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133   -2.0537   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807   -2.5256    0.7728 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1148   -1.6403    1.7676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576   -0.4085    1.2070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3998    0.1641    2.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085    0.4219    0.8787 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.7510    0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3298    2.6609    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0852    4.0106    1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660    4.4808    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090    5.8432    0.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1882    3.5395    0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875    4.1548    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417    2.2157    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088    1.0922    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315    0.8616    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -0.4725   -0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -1.5144    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -2.8836   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6602   -3.7206   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3967   -5.0988   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483   -5.6058   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070   -4.7559    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3629   -3.4127    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571   -2.4063    0.4631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536   -1.2595    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8331    0.0239    0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8672   -0.4963   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6774   -1.4526   -0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886    0.8555   -0.4413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614    1.7187   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    2.9208   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0902    2.5262   -2.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    0.7578   -3.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1935    1.2057   -1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718    2.4477   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8108    1.1355   -3.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -2.1898    0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3372   -2.8070   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -1.7002   -1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -3.5702    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -0.6756    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540    0.8583    2.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    0.4804    2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.3630    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    4.7296    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    6.2531    0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606    4.3440   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9923    4.4871    0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6421   -3.3819   -0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263   -5.7336   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419   -6.6863   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081   -5.1328    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2762    1.1636   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 24 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 38 39  2  0
 11  6  1  0
 34 13  1  0
 32  9  1  0
 21 14  1  0
 34 22  1  0
 38 23  1  0
 33 25  1  0
 31 26  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  1
 12 49  1  0
 12 50  1  0
 12 51  1  0
 15 52  1  0
 16 53  1  0
 18 54  1  0
 20 55  1  0
 20 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 37 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Ethyl (15S,16S,18R)-9-amino-3,10,16-trihydroxy-15-methyl-5-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1,.0,.0,.0,.0,.0,]octacosa-1,3,6,8(13),9,11,20,22,24,26-decaene-16-carboxylic acid	Generator

Chemical Formula

C₂₈H₂₂N₄O₇

Average Mass

526.5050 Da

Monoisotopic Mass

526.14885 Da

IUPAC Name

ethyl (15S,16S,18R)-9-amino-10,16-dihydroxy-15-methyl-3,5-dioxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^{15,18}.0^{2,6}.0^{7,27}.0^{8,13}.0^{19,26}.0^{20,25}]octacosa-1,6,8,10,12,20,22,24,26-nonaene-16-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCOC(=O)[C@]1(O)C[C@H]2O[C@]1(C)N1C3=C(C4=C5C(=O)NC(=O)C5=C5C6=CC=CC=C6N2C5=C14)C(N)=C(O)C=C3

InChI Identifier

InChI=1S/C28H22N4O7/c1-3-38-26(36)28(37)10-15-31-12-7-5-4-6-11(12)16-19-20(25(35)30-24(19)34)18-17-13(8-9-14(33)21(17)29)32(23(18)22(16)31)27(28,2)39-15/h4-9,15,33,37H,3,10,29H2,1-2H3,(H,30,34,35)/t15-,27+,28-/m1/s1

InChI Key

VEXMHCAEEISMPG-ZXOINBKBSA-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	12061542

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. TA-0363	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Pyrroloindole
Phthalimide
Hydroxyindole
Isoindolone
Indole
Isoindoline
Isoindole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Carboxylic acid imide
Heteroaromatic compound
Carboxylic acid imide, n-unsubstituted
Oxolane
Pyrrole
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Primary amine
Carbonyl group
Organonitrogen 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	2.64	ALOGPS
logP	2.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	1.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	138.28 m³·mol⁻¹	ChemAxon
Polarizability	53.8 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011585

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8134118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9958509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsuura N, Tamehiro N, Andoh T, Kawashima A, Ubukata M: Indocarbazostatin and indocarbazostatin B, novel inhibitors of NGF-induced neuronal differentiation in PC12 cells. I. Screening, taxonomy, fermentation and biological activities. J Antibiot (Tokyo). 2002 Apr;55(4):355-62. doi: 10.7164/antibiotics.55.355. [PubMed:12061542 ]
Feng Y, Matsuura N, Ubukata M: Indocarbazostatins C and D, new inhibitors of NGF-induced neuronal differentiation in PC12 cells. J Antibiot (Tokyo). 2004 Oct;57(10):627-33. doi: 10.7164/antibiotics.57.627. [PubMed:15638322 ]
Feng Y, Mitsuhashi S, Kishimoto T, Ubukata M: Biosynthesis of indocarbazostatin B, incorporation of D-[U-13C] glucose and L-[2-13C] tryptophan. J Antibiot (Tokyo). 2005 Dec;58(12):759-65. doi: 10.1038/ja.2005.103. [PubMed:16506693 ]
Tamehiro N, Matsuura N, Feng Y, Nakajima N, Ubukata M: Indocarbazostatin and indocarbazostatin B, novel inhibitors of NGF-induced Neuronal differentiation in PC12 cells. II. Isolation, physicochemical properties and structural elucidation. J Antibiot (Tokyo). 2002 Apr;55(4):363-70. doi: 10.7164/antibiotics.55.363. [PubMed:12061543 ]

Showing NP-Card for Indocarbazostatin B (NP0004201)

MOL for NP0004201 (Indocarbazostatin B)

3D MOL for NP0004201 (Indocarbazostatin B)

3D SDF for NP0004201 (Indocarbazostatin B)

3D-SDF for NP0004201 (Indocarbazostatin B)

PDB for NP0004201 (Indocarbazostatin B)

3D PDB for NP0004201 (Indocarbazostatin B)

SMILES for NP0004201 (Indocarbazostatin B)

INCHI for NP0004201 (Indocarbazostatin B)

Structure for NP0004201 (Indocarbazostatin B)

3D Structure for NP0004201 (Indocarbazostatin B)