NP-MRD: Showing NP-Card for β-Rubromycin (NP0014023)

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Record Information

Version

1.0

Created at

2021-01-05 23:17:07 UTC

Updated at

2021-07-15 17:16:09 UTC

NP-MRD ID

NP0014023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-Rubromycin

Provided By

NPAtlas

Description

Beta-Rubromycin is also known as β-rubromycin. β-Rubromycin is found in Streptomyces collinus. It was first documented in 2012 (PMID: 22876944). Based on a literature review very few articles have been published on beta-Rubromycin (PMID: 25855820) (PMID: 33629382) (PMID: 33339950) (PMID: 31833370).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


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   -4.9195    4.6183   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2581    2.7830   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3266    3.6403   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6358    3.2497   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262    1.4645   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3684    0.5881   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4857   -0.7654    0.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6906   -1.3679    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037    1.0408   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    0.1018   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -1.0990   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0815   -4.1142    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025   -4.5447    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4441   -5.5007    2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7564   -2.2243    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -0.8743    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391   -0.0437   -3.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2049    2.5221    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    1.4887    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -0.1534    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    1.2564    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.6676   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.8152   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1683    5.1485   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2674    4.1378    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6435    2.5102    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1018    2.7773   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987    1.0438    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585   -1.1153   -0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9678   -1.0830    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -2.4709    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 16  5  1  0  0  0  0
 24 18  1  0  0  0  0
 37 27  1  0  0  0  0
 13  7  1  0  0  0  0
 38 22  1  0  0  0  0
 20  9  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  6 43  1  0  0  0  0
  8 44  1  0  0  0  0
 12 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 29 52  1  0  0  0  0
 32 53  1  0  0  0  0
 32 54  1  0  0  0  0
 32 55  1  0  0  0  0
 33 56  1  0  0  0  0
 36 57  1  0  0  0  0
 36 58  1  0  0  0  0
 36 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(C(=O)C2=C(OC([H])([H])[H])C([H])=C1OC([H])([H])[H])C([H])([H])[C@]1(O3)OC2=C(C([H])=C3C([H])=C(OC(=O)C3=C2O[H])C(=O)OC([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)19(28)12-9-27(39-24(12)22(18)31)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)21(30)23(10)38-27/h6-8,29-30H,4-5,9H2,1-3H3/t27-/m0/s1

> <INCHI_KEY>
FXCBZGHGMRSWJD-MHZLTWQESA-N

> <FORMULA>
C27H20O12

> <MOLECULAR_WEIGHT>
536.445

> <EXACT_MASS>
536.095476084

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
53.61593504220887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.706319380666666

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.099157117347843

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9823395976161784

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4671323410991457

> <JCHEM_POLAR_SURFACE_AREA>
164.12

> <JCHEM_REFRACTIVITY>
133.44669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
    8.8676   -4.4578    2.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8684   -3.7206    2.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7586   -3.5758    0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6057   -4.1351    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.8010    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7302   -2.1517    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -1.4145    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530   -0.7742    0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578   -0.0467    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790    0.0078   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -0.6203   -1.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.5749   -3.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7362   -1.3539   -1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218   -2.0121   -1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6768   -1.9168   -3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308   -2.6838   -1.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.7360   -1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5985    1.0485   -1.0220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7980    1.4841    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220    0.6245    1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365   -0.1611   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    0.5646   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5165    1.8320   -1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    2.0758   -1.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    2.8104   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160    4.0013   -1.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    2.3853   -0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058    3.2980   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9195    4.6183   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2581    2.7830   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3266    3.6403   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6358    3.2497   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262    1.4645   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3684    0.5881   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4857   -0.7654    0.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6906   -1.3679    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037    1.0408   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    0.1018   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -1.0990   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0815   -4.1142    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025   -4.5447    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4441   -5.5007    2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7564   -2.2243    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -0.8743    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391   -0.0437   -3.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2049    2.5221    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    1.4887    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -0.1534    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    1.2564    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.6676   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.8152   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1683    5.1485   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2674    4.1378    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6435    2.5102    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1018    2.7773   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987    1.0438    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585   -1.1153   -0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9678   -1.0830    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -2.4709    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  6
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 38 39  2  0
 16  5  1  0
 24 18  1  0
 37 27  1  0
 13  7  1  0
 38 22  1  0
 20  9  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  8 44  1  0
 12 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 29 52  1  0
 32 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  0
 36 57  1  0
 36 58  1  0
 36 59  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       8.868  -4.458   2.767  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.868  -3.721   2.094  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.759  -3.576   0.739  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.606  -4.135   0.002  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.704  -2.801   0.095  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.730  -2.152   0.819  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.723  -1.415   0.227  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.753  -0.774   0.978  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.758  -0.047   0.353  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.779   0.008  -1.015  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.732  -0.620  -1.763  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.766  -0.575  -3.152  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.736  -1.354  -1.146  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.722  -2.012  -1.843  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.677  -1.917  -3.101  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.631  -2.684  -1.209  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.786   0.736  -1.690  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.599   1.048  -1.022  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.798   1.484   0.390  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.722   0.625   1.199  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.337  -0.161  -1.116  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.657   0.565  -1.014  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.517   1.832  -1.321  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.166   2.076  -1.658  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.624   2.810  -1.302  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.416   4.001  -1.606  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.958   2.385  -0.929  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.006   3.298  -0.899  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.920   4.618  -1.203  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.258   2.783  -0.516  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.327   3.640  -0.466  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.636   3.250  -0.097  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.426   1.464  -0.195  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.368   0.588  -0.236  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.486  -0.765   0.080  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.691  -1.368   0.476  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.104   1.041  -0.607  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.982   0.102  -0.638  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.170  -1.099  -0.338  0.00  0.00           O+0
HETATM   40  H   UNK     0       9.082  -4.114   3.779  0.00  0.00           H+0
HETATM   41  H   UNK     0       9.803  -4.545   2.218  0.00  0.00           H+0
HETATM   42  H   UNK     0       8.444  -5.501   2.851  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.756  -2.224   1.892  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.818  -0.874   2.068  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.039  -0.044  -3.612  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.205   2.522   0.397  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.212   1.489   0.891  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.090  -0.153   1.722  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.202   1.256   1.983  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.222  -0.668  -2.088  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.171  -0.815  -0.240  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.168   5.149  -1.480  0.00  0.00           H+0
HETATM   53  H   UNK     0      -9.267   4.138   0.156  0.00  0.00           H+0
HETATM   54  H   UNK     0      -8.643   2.510   0.725  0.00  0.00           H+0
HETATM   55  H   UNK     0      -9.102   2.777  -0.984  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.399   1.044   0.103  0.00  0.00           H+0
HETATM   57  H   UNK     0      -7.458  -1.115  -0.283  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.968  -1.083   1.494  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.499  -2.471   0.456  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7   43                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   44                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   45                                                       
CONECT   13   11   14    7                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5                                                       
CONECT   17   10   18                                                       
CONECT   18   17   19   21   24                                             
CONECT   19   18   20   46   47                                             
CONECT   20   19    9   48   49                                             
CONECT   21   18   22   50   51                                             
CONECT   22   21   23   38                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   18                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   52                                                       
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   53   54   55                                             
CONECT   33   30   34   56                                                  
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   57   58   59                                             
CONECT   37   34   38   27                                                  
CONECT   38   37   39   22                                                  
CONECT   39   38                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45   12                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   29                                                            
CONECT   53   32                                                            
CONECT   54   32                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   36                                                            
CONECT   58   36                                                            
CONECT   59   36                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  128    0
END

RDKit          3D

59 64  0  0  0  0  0  0  0  0999 V2000
    8.8676   -4.4578    2.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8684   -3.7206    2.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7586   -3.5758    0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6057   -4.1351    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.8010    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7302   -2.1517    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -1.4145    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530   -0.7742    0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578   -0.0467    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7790    0.0078   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -0.6203   -1.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.5749   -3.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7362   -1.3539   -1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7218   -2.0121   -1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6768   -1.9168   -3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308   -2.6838   -1.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.7360   -1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5985    1.0485   -1.0220 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7980    1.4841    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220    0.6245    1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365   -0.1611   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    0.5646   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5165    1.8320   -1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    2.0758   -1.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236    2.8104   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160    4.0013   -1.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    2.3853   -0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0058    3.2980   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9195    4.6183   -1.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2581    2.7830   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3266    3.6403   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6358    3.2497   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262    1.4645   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3684    0.5881   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4857   -0.7654    0.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6906   -1.3679    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037    1.0408   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    0.1018   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -1.0990   -0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0815   -4.1142    3.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025   -4.5447    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4441   -5.5007    2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7564   -2.2243    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -0.8743    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391   -0.0437   -3.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2049    2.5221    0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    1.4887    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901   -0.1534    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    1.2564    1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.6676   -2.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -0.8152   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1683    5.1485   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2674    4.1378    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6435    2.5102    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1018    2.7773   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987    1.0438    0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585   -1.1153   -0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9678   -1.0830    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -2.4709    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  6
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 38 39  2  0
 16  5  1  0
 24 18  1  0
 37 27  1  0
 13  7  1  0
 38 22  1  0
 20  9  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  8 44  1  0
 12 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 29 52  1  0
 32 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  0
 36 57  1  0
 36 58  1  0
 36 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
b-Rubromycin	Generator
Β-rubromycin	Generator
Methyl (2S)-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylic acid	Generator

Chemical Formula

C₂₇H₂₀O₁₂

Average Mass

536.4450 Da

Monoisotopic Mass

536.09548 Da

IUPAC Name

methyl (2S)-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

Traditional Name

methyl (2S)-8,10'-dihydroxy-5,7-dimethoxy-4,9,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=CC3=C(O[C@@]4(CC5=C(O4)C(=O)C4=C(C5=O)C(OC)=CC(OC)=C4O)CC3)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)19(28)12-9-27(39-24(12)22(18)31)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)21(30)23(10)38-27/h6-8,29-30H,4-5,9H2,1-3H3/t27-/m0/s1

InChI Key

FXCBZGHGMRSWJD-MHZLTWQESA-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 collinus	NPAtlas	25855820

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.79	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	164.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.45 m³·mol⁻¹	ChemAxon
Polarizability	53.62 Å³	ChemAxon
Number of Rings	6	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

NPA020512

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4576519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5464074

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Erratum: Borderud SP, Li Y, Burkhalter JE, Sheffer CE and Ostroff JS. Electronic cigarette use among patients with cancer: Characteristics of electronic cigarette users and their smoking cessation outcomes. Cancer. doi: 10.1002/ cncr.28811. Cancer. 2015 Mar 1;121(5):800. doi: 10.1002/cncr.29118. [PubMed:25855820 ]
Yi L, Kong J, Xiong Y, Yi S, Gan T, Huang C, Duan Y, Zhu X: Genome mining of Streptomyces sp. CB00271 as a natural high-producer of beta-rubromycin and the resulting discovery of beta-rubromycin acid. Biotechnol Bioeng. 2021 Jun;118(6):2243-2254. doi: 10.1002/bit.27732. Epub 2021 Mar 25. [PubMed:33629382 ]
Tani S, Nishio N, Kai K, Hagiwara D, Ogata Y, Tojo M, Sumitani JI, Judelson HS, Kawaguchi T: Chemical genetic approach using beta-rubromycin reveals that a RIO kinase-like protein is involved in morphological development in Phytophthora infestans. Sci Rep. 2020 Dec 18;10(1):22326. doi: 10.1038/s41598-020-79326-7. [PubMed:33339950 ]
Wang X, Elshahawi SI, Ponomareva LV, Ye Q, Liu Y, Copley GC, Hower JC, Hatcher BE, Kharel MK, Van Lanen SG, She QB, Voss SR, Thorson JS, Shaaban KA: Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces. J Nat Prod. 2019 Dec 27;82(12):3469-3476. doi: 10.1021/acs.jnatprod.9b01015. Epub 2019 Dec 13. [PubMed:31833370 ]
Mizushina Y, Takeuchi T, Sugawara F, Yoshida H: Anti-cancer targeting telomerase inhibitors: beta-rubromycin and oleic acid. Mini Rev Med Chem. 2012 Oct;12(11):1135-43. doi: 10.2174/138955712802762220. [PubMed:22876944 ]

Showing NP-Card for β-Rubromycin (NP0014023)

MOL for NP0014023 (β-Rubromycin)

3D MOL for NP0014023 (β-Rubromycin)

3D SDF for NP0014023 (β-Rubromycin)

3D-SDF for NP0014023 (β-Rubromycin)

PDB for NP0014023 (β-Rubromycin)

3D PDB for NP0014023 (β-Rubromycin)

SMILES for NP0014023 (β-Rubromycin)

INCHI for NP0014023 (β-Rubromycin)

Structure for NP0014023 (β-Rubromycin)

3D Structure for NP0014023 (β-Rubromycin)