NP-MRD: Showing NP-Card for Mumbaistatin (NP0003717)

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Record Information

Version

2.0

Created at

2020-12-09 00:53:24 UTC

Updated at

2021-07-15 16:47:11 UTC

NP-MRD ID

NP0003717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mumbaistatin

Provided By

NPAtlas

Description

Mumbaistatin is found in Streptomyces. Mumbaistatin was first documented in 2001 (PMID: 11426660). Based on a literature review very few articles have been published on 1-[2-(5-carboxy-4-hydroxypentanoyl)-6-hydroxybenzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (PMID: 21274958) (PMID: 20486934) (PMID: 19074414) (PMID: 17524653).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 60 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117493D          

 60 63  0  0  0  0            999 V2000
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   -2.8860   -3.1151   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249   -3.3357   -2.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7737   -4.2092   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731   -4.1212   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1489   -2.9441    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -1.8812    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893   -0.6336    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6126   -0.5817    1.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -2.0113   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895   -3.4288    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.8023    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -1.1219   -0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.5359    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.7424    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9865    3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    1.2826    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    0.4097    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    1.5096    0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    2.2142   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2192    2.6083   -3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    2.6152   -4.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9090    1.7774    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644   -2.7691   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961   -5.1472   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5976   -4.9155   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -2.8379    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  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  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 13 14  2  0  0  0  0
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 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
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 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
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 29 20  1  0  0  0  0
 38 32  1  0  0  0  0
 39 28  1  0  0  0  0
  3 41  1  0  0  0  0
  4 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  6  0  0  0
  6 45  1  0  0  0  0
  7 46  1  0  0  0  0
  7 47  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
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 34 57  1  0  0  0  0
 35 58  1  0  0  0  0
 36 59  1  0  0  0  0
 37 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(C(=O)C2=C(O[H])C([H])=C([H])C([H])=C2C(=O)C([H])([H])C([H])([H])[C@@]([H])(O[H])C([H])([H])C(=O)O[H])C2=C(C([H])=C1O[H])C(=O)C1=C([H])C([H])=C([H])C(O[H])=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H20O12/c29-11(9-19(34)35)7-8-15(30)12-3-1-5-16(31)20(12)27(38)24-22-14(10-18(33)23(24)28(39)40)25(36)13-4-2-6-17(32)21(13)26(22)37/h1-6,10-11,29,31-33H,7-9H2,(H,34,35)(H,39,40)/t11-/m1/s1

> <INCHI_KEY>
XFESZXMDORIFAO-UHFFFAOYSA-N

> <FORMULA>
C28H20O12

> <MOLECULAR_WEIGHT>
548.456

> <EXACT_MASS>
548.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.00972285694062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
4.115782583666667

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.3084088326928094

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4488952862741127

> <JCHEM_PKA_STRONGEST_BASIC>
-2.806192812452971

> <JCHEM_POLAR_SURFACE_AREA>
223.79999999999995

> <JCHEM_REFRACTIVITY>
136.93899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
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    2.0785    0.4331    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607    0.7773    1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0459    0.4979    1.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.4022   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9531    1.6190   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218    2.0484   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163    2.2749   -2.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    2.0697   -2.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1392    1.4563   -2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7516    1.5683   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162    2.7656    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409    3.9443    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    4.0184   -0.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2395    2.7995    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5213    4.0294    1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    1.7057    1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037    0.5349    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    0.4461   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -0.8068   -0.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2372   -0.8565   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -1.9446   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860   -3.1151   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249   -3.3357   -2.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7737   -4.2092   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731   -4.1212   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1489   -2.9441    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -1.8812    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893   -0.6336    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6126   -0.5817    1.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2895   -3.4288    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.8023    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -1.1219   -0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.5359    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.7424    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9865    3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    1.2826    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    0.4097    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    1.5096    0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    2.2142   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2192    2.6083   -3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    2.6152   -4.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723    5.7215    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2987    4.1879    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9090    1.7774    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644   -2.7691   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961   -5.1472   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5976   -4.9155   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -2.8379    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 17 11  1  0
 29 20  1  0
 38 32  1  0
 39 28  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  6
  6 45  1  0
  7 46  1  0
  7 47  1  0
  8 48  1  0
  8 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 16 53  1  0
 24 54  1  0
 26 55  1  0
 27 56  1  0
 34 57  1  0
 35 58  1  0
 36 59  1  0
 37 60  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  O   UNK     0       4.802  -3.374  -1.051  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.163  -2.979   0.083  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.516  -2.789   0.286  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.128  -2.733   1.160  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.638  -1.258   0.970  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.890  -0.566   1.136  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.723  -0.910   2.070  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.079   0.433   2.113  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.161   0.777   1.023  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.046   0.498   1.216  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.597   1.402  -0.227  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.953   1.619  -0.334  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.522   2.048  -1.498  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.716   2.275  -2.587  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.381   2.070  -2.481  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.594   2.309  -3.626  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.745   1.624  -1.290  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.658   1.550  -1.310  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.139   1.456  -2.549  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.752   1.568  -0.410  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.116   2.766   0.257  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.341   3.944   0.040  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.276   4.018  -0.679  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.714   5.138   0.612  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.240   2.800   1.052  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.521   4.029   1.675  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.024   1.706   1.217  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.704   0.535   0.588  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.589   0.446  -0.217  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.285  -0.807  -0.891  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.237  -0.857  -1.619  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.146  -1.945  -0.722  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.886  -3.115  -1.392  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.825  -3.336  -2.210  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.774  -4.209  -1.236  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.873  -4.121  -0.444  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.149  -2.944   0.245  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.258  -1.881   0.070  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.589  -0.634   0.765  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.613  -0.582   1.502  0.00  0.00           O+0
HETATM   41  H   UNK     0       6.994  -2.011  -0.205  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.289  -3.429   1.107  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.629  -2.802   2.137  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.322  -1.122  -0.056  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.944  -0.536   2.153  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.980  -1.742   2.200  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.312  -0.987   3.046  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.788   1.283   2.361  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.438   0.410   3.079  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.601   1.510   0.564  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.588   2.214  -1.572  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.219   2.608  -3.474  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.970   2.615  -4.492  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.472   5.721   0.248  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.299   4.188   2.287  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.909   1.777   1.870  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.064  -2.769  -2.434  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.596  -5.147  -1.754  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.598  -4.915  -0.290  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.987  -2.838   0.863  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   41                                                       
CONECT    4    2    5   42   43                                             
CONECT    5    4    6    7   44                                             
CONECT    6    5   45                                                       
CONECT    7    5    8   46   47                                             
CONECT    8    7    9   48   49                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   50                                                  
CONECT   13   12   14   51                                                  
CONECT   14   13   15   52                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   53                                                       
CONECT   17   15   18   11                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   29                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   54                                                       
CONECT   25   21   26   27                                                  
CONECT   26   25   55                                                       
CONECT   27   25   28   56                                                  
CONECT   28   27   29   39                                                  
CONECT   29   28   30   20                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   57                                                       
CONECT   35   33   36   58                                                  
CONECT   36   35   37   59                                                  
CONECT   37   36   38   60                                                  
CONECT   38   37   39   32                                                  
CONECT   39   38   40   28                                                  
CONECT   40   39                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46    7                                                            
CONECT   47    7                                                            
CONECT   48    8                                                            
CONECT   49    8                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   16                                                            
CONECT   54   24                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   34                                                            
CONECT   58   35                                                            
CONECT   59   36                                                            
CONECT   60   37                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    4.8018   -3.3739   -1.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630   -2.9794    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5158   -2.7895    0.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275   -2.7328    1.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -1.2585    0.9703 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8904   -0.5661    1.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -0.9100    2.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785    0.4331    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607    0.7773    1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0459    0.4979    1.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.4022   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9531    1.6190   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218    2.0484   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7163    2.2749   -2.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    2.0697   -2.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    2.3091   -3.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448    1.6240   -1.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    1.5501   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1392    1.4563   -2.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7516    1.5683   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162    2.7656    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409    3.9443    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    4.0184   -0.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145    5.1380    0.6115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    2.7995    1.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5213    4.0294    1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    1.7057    1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037    0.5349    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    0.4461   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -0.8068   -0.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2372   -0.8565   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -1.9446   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860   -3.1151   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249   -3.3357   -2.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7737   -4.2092   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8731   -4.1212   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1489   -2.9441    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -1.8812    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893   -0.6336    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6126   -0.5817    1.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -2.0113   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895   -3.4288    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.8023    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -1.1219   -0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.5359    2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.7424    2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -0.9865    3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    1.2826    2.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    0.4097    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    1.5096    0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    2.2142   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2192    2.6083   -3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    2.6152   -4.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723    5.7215    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2987    4.1879    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9090    1.7774    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644   -2.7691   -2.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5961   -5.1472   -1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5976   -4.9155   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -2.8379    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 17 11  1  0
 29 20  1  0
 38 32  1  0
 39 28  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  6
  6 45  1  0
  7 46  1  0
  7 47  1  0
  8 48  1  0
  8 49  1  0
 12 50  1  0
 13 51  1  0
 14 52  1  0
 16 53  1  0
 24 54  1  0
 26 55  1  0
 27 56  1  0
 34 57  1  0
 35 58  1  0
 36 59  1  0
 37 60  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1-[2-(5-Carboxy-4-hydroxypentanoyl)-6-hydroxybenzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	Generator

Chemical Formula

C₂₈H₂₀O₁₂

Average Mass

548.4560 Da

Monoisotopic Mass

548.09548 Da

IUPAC Name

1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(CCC(=O)C1=C(C(=O)C2=C3C(=O)C4=C(C=CC=C4O)C(=O)C3=CC(O)=C2C(O)=O)C(O)=CC=C1)CC(O)=O

InChI Identifier

InChI=1S/C28H20O12/c29-11(9-19(34)35)7-8-15(30)12-3-1-5-16(31)20(12)27(38)24-22-14(10-18(33)23(24)28(39)40)25(36)13-4-2-6-17(32)21(13)26(22)37/h1-6,10-11,29,31-33H,7-9H2,(H,34,35)(H,39,40)

InChI Key

XFESZXMDORIFAO-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	NPAtlas	11426660

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
Hydroxyanthraquinone
Benzophenone
Alkyl-phenylketone
Aryl-phenylketone
2-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid or derivatives
Butyrophenone
Hydroxybenzoic acid
Salicylic acid or derivatives
Phenylketone
Medium-chain keto acid
Aryl ketone
Aryl alkyl ketone
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Dicarboxylic acid or derivatives
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.1	ALOGPS
logP	4.12	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.45	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	223.8 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.94 m³·mol⁻¹	ChemAxon
Polarizability	52.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA006115

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8026187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9850474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vertesy L, Kurz M, Paulus EF, Schummer D, Hammann P: The chemical structure of mumbaistatin, a novel glucose-6-phosphate translocase inhibitor produced by Streptomyces sp. DSM 11641. J Antibiot (Tokyo). 2001 Apr;54(4):354-63. doi: 10.7164/antibiotics.54.354. [PubMed:11426660 ]
Neufeind S, Hulsken N, Neudorfl JM, Schlorer N, Schmalz HG: Total synthesis of cyclo-mumbaistatin analogues through anionic homo-Fries rearrangement. Chemistry. 2011 Feb 25;17(9):2633-41. doi: 10.1002/chem.201003166. Epub 2011 Jan 27. [PubMed:21274958 ]
Tahanian E, Lord-Dufour S, Das A, Khosla C, Roy R, Annabi B: Inhibition of tubulogenesis and of carcinogen-mediated signaling in brain endothelial cells highlight the antiangiogenic properties of a mumbaistatin analog. Chem Biol Drug Des. 2010 May;75(5):481-8. doi: 10.1111/j.1747-0285.2010.00961.x. [PubMed:20486934 ]
Lord-Dufour S, Copland IB, Levros LC Jr, Post M, Das A, Khosla C, Galipeau J, Rassart E, Annabi B: Evidence for transcriptional regulation of the glucose-6-phosphate transporter by HIF-1alpha: Targeting G6PT with mumbaistatin analogs in hypoxic mesenchymal stromal cells. Stem Cells. 2009 Mar;27(3):489-97. doi: 10.1634/stemcells.2008-0855. [PubMed:19074414 ]
Lee TS, Das A, Khosla C: Structure-activity relationships of semisynthetic mumbaistatin analogs. Bioorg Med Chem. 2007 Aug 1;15(15):5207-18. doi: 10.1016/j.bmc.2007.05.019. Epub 2007 May 23. [PubMed:17524653 ]

Showing NP-Card for Mumbaistatin (NP0003717)

MOL for NP0003717 (Mumbaistatin)

3D MOL for NP0003717 (Mumbaistatin)

3D SDF for NP0003717 (Mumbaistatin)

3D-SDF for NP0003717 (Mumbaistatin)

PDB for NP0003717 (Mumbaistatin)

3D PDB for NP0003717 (Mumbaistatin)

SMILES for NP0003717 (Mumbaistatin)

INCHI for NP0003717 (Mumbaistatin)

Structure for NP0003717 (Mumbaistatin)

3D Structure for NP0003717 (Mumbaistatin)