NP-MRD: Showing NP-Card for epsilon-Rhodomycinone (NP0079031)

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Record Information

Version

1.0

Created at

2022-04-29 00:06:43 UTC

Updated at

2022-04-29 00:06:43 UTC

NP-MRD ID

NP0079031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epsilon-Rhodomycinone

Description

Epsilon-rhodomycinone, also known as NSC 196524, belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. Epsilon-rhodomycinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. epsilon-Rhodomycinone is found in Nonomuria sp. NN22303, Streptomyces coeruleorubidus, Streptomyces galilaeus, Streptomyces peucetius, Streptomyces purpurascens and Streptomyces sp. MST77755. It was first documented in 2000 (PMID: 10757705). Based on a literature review a significant number of articles have been published on epsilon-rhodomycinone (PMID: 15497950) (PMID: 15480939) (PMID: 16797766) (PMID: 19651502).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202062D          

 31 34  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -0.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
 19 23  1  1  0  0  0
 23 24  1  0  0  0  0
 19 25  1  6  0  0  0
 18 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.9322    2.4730    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.2676   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    1.1186   -0.0778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2707    2.3382   -0.4670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058    1.0217    1.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281    0.0414    1.9529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4398    0.5155    3.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316   -0.0015    1.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6517   -0.0467    1.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -0.0380    2.9790 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7405   -0.0963    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6148   -0.1033   -0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221   -0.0576   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240   -0.0667   -2.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663   -0.0075   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482    0.0521   -0.8412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7437   -1.2996   -0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -1.5849   -0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0822   -2.3698   -1.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958   -3.6846   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693   -0.1558   -1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -0.1608   -2.7604 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180   -0.2036   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2429   -0.2540   -1.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133   -0.2987   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6332   -0.2915    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5352   -0.2416    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -0.2345    2.3615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -0.1980    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017   -0.1446    1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743   -0.1407    2.5146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1955    2.9417    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542    3.2017   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8028    2.1889    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023    1.5010   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9541    0.4106   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964    2.3254   -1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    0.8053    1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5583    2.0337    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2698   -0.9756    2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753    1.5090    3.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.0596    3.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -0.0431   -3.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    0.3621   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1338   -3.8172   -0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -4.4314   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -3.9114   -2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1131   -0.2584   -2.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -0.3385   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6007   -0.3250    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794   -0.2668    2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 16  3  1  0
 29 23  1  0
 15  8  1  0
 30 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  7 41  1  0
 10 42  1  0
 14 43  1  0
 16 44  1  6
 20 45  1  0
 20 46  1  0
 20 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 28 51  1  0
M  END


  Mrv1652304292202062D          

 31 34  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -0.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
 19 23  1  1  0  0  0
 23 24  1  0  0  0  0
 19 25  1  6  0  0  0
 18 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C[C@H](O)C2=C(O)C3=C(C(O)=C2[C@H]1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O9/c1-3-22(30)7-10(24)12-13(16(22)21(29)31-2)20(28)14-15(19(12)27)18(26)11-8(17(14)25)5-4-6-9(11)23/h4-6,10,16,23-24,27-28,30H,3,7H2,1-2H3/t10-,16-,22+/m0/s1

> <INCHI_KEY>
PYFOXRACBORDCT-GOSXWKPOSA-N

> <FORMULA>
C22H20O9

> <MOLECULAR_WEIGHT>
428.393

> <EXACT_MASS>
428.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.287792015482395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.0475858083333334

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.520703391549182

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.899911849402928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.232715675033897

> <JCHEM_POLAR_SURFACE_AREA>
161.58999999999997

> <JCHEM_REFRACTIVITY>
107.73449999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rhodomycinone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.816  -1.306   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.355  -1.252   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.539  -0.054   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   30                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   26                                                  
CONECT   19   18   20   23   25                                             
CONECT   20   19   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24                                                       
CONECT   24   23                                                            
CONECT   25   19                                                            
CONECT   26   18   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   13                                                            
CONECT   31    3                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
e-Rhodomycinone	ChEBI
NSC 196524	ChEBI
Rhodomycinone	ChEBI

Chemical Formula

C₂₂H₂₀O₉

Average Mass

428.3930 Da

Monoisotopic Mass

428.11073 Da

IUPAC Name

methyl (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

rhodomycinone

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O)C[C@H](O)C2=C(O)C3=C(C(O)=C2[C@H]1C(=O)OC)C(=O)C1=CC=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C22H20O9/c1-3-22(30)7-10(24)12-13(16(22)21(29)31-2)20(28)14-15(19(12)27)18(26)11-8(17(14)25)5-4-6-9(11)23/h4-6,10,16,23-24,27-28,30H,3,7H2,1-2H3/t10-,16-,22+/m0/s1

InChI Key

PYFOXRACBORDCT-GOSXWKPOSA-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
Nonomuria sp. NN22303	-	KNApSAcK
Streptomyces coeruleorubidus	LOTUS Database	35616633
Streptomyces galilaeus	LOTUS Database	35616633
Streptomyces peucetius	LOTUS Database	35616633
Streptomyces purpurascens	LOTUS Database	35616633
Streptomyces sp. MST77755	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
1,4-anthraquinone
9,10-anthraquinone
Anthracene
1-naphthalenecarboxylic acid or derivatives
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Methyl ester
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:75291 )
methyl ester (CHEBI:75291 )
carbopolycyclic compound (CHEBI:75291 )
tetracenomycin (CHEBI:75291 )
tetracenequinones (CHEBI:75291 )

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	2.63	ALOGPS
logP	3.05	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.73 m³·mol⁻¹	ChemAxon
Polarizability	42.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99207

PDB ID

Not Available

ChEBI ID

75291

Good Scents ID

Not Available

References

General References

Clark B, Capon RJ, Stewart M, Lacey E, Tennant S, Gill JH: Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp. J Nat Prod. 2004 Oct;67(10):1729-31. doi: 10.1021/np049826v. [PubMed:15497950 ]
Pfefferle CM, Breinholt J, Olsen CE, Kroppenstedt RM, Wellington EM, Gurtler H, Fiedler HP: Kyanomycin, a complex of unusual anthracycline-phospholipid hybrids from Nonomuria species. J Nat Prod. 2000 Mar;63(3):295-8. doi: 10.1021/np9904408. [PubMed:10757705 ]
Kiviharju K, Leisola M, Eerikainen T: Optimization of Streptomyces peucetius var. caesius N47 cultivation and epsilon-rhodomycinone production using experimental designs and response surface methods. J Ind Microbiol Biotechnol. 2004 Nov;31(10):475-81. doi: 10.1007/s10295-004-0172-3. Epub 2004 Oct 7. [PubMed:15480939 ]
Kiviharju K, Salonen K, Leisola M, Eerikainen T: Modeling and simulation of Streptomyces peucetius var. caesius N47 cultivation and epsilon-rhodomycinone production with kinetic equations and neural networks. J Biotechnol. 2006 Nov 10;126(3):365-73. doi: 10.1016/j.jbiotec.2006.04.034. Epub 2006 May 6. [PubMed:16797766 ]
Malla S, Niraula NP, Liou K, Sohng JK: Self-resistance mechanism in Streptomyces peucetius: overexpression of drrA, drrB and drrC for doxorubicin enhancement. Microbiol Res. 2010 May 30;165(4):259-67. doi: 10.1016/j.micres.2009.04.002. Epub 2009 Aug 3. [PubMed:19651502 ]

Showing NP-Card for epsilon-Rhodomycinone (NP0079031)

MOL for NP0079031 (epsilon-Rhodomycinone)

3D MOL for NP0079031 (epsilon-Rhodomycinone)

3D SDF for NP0079031 (epsilon-Rhodomycinone)

3D-SDF for NP0079031 (epsilon-Rhodomycinone)

PDB for NP0079031 (epsilon-Rhodomycinone)

3D PDB for NP0079031 (epsilon-Rhodomycinone)

SMILES for NP0079031 (epsilon-Rhodomycinone)

INCHI for NP0079031 (epsilon-Rhodomycinone)

Structure for NP0079031 (epsilon-Rhodomycinone)

3D Structure for NP0079031 (epsilon-Rhodomycinone)