NP-MRD: Showing NP-Card for Rubiginone B2 (NP0010484)

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Record Information

Version

2.0

Created at

2021-01-05 19:59:20 UTC

Updated at

2021-07-15 17:06:13 UTC

NP-MRD ID

NP0010484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubiginone B2

Provided By

NPAtlas

Description

(3S)-8-methoxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. Rubiginone B2 is found in Streptomyces griseorubiginosus. Rubiginone B2 was first documented in 2005 (PMID: 16238336). Based on a literature review very few articles have been published on (3S)-8-methoxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione (PMID: 23549355) (PMID: 20575121) (PMID: 17625884).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107383D          

 40 43  0  0  0  0            999 V2000
    5.8139   -1.4356    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -1.2079    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -0.1580   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.7238   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.7709   -1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029    1.9429   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    1.0467   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.0040   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.9306    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8947    1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.7733    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.6415    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.5345    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.4982    1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    0.4086    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.2821    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.2231   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.1660   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    1.5309   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    2.6468   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6986    1.2927   -0.9212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4664    0.2017   -0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4793   -1.0167   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2295    1.0763 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3544   -0.4810    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -2.2081    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165   -1.7479   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520    0.5787   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328    2.4794   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    2.7497   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323   -2.4712    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -2.1905    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.0731   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2678    2.2426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.5231   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.4182   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427   -0.7723   -2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -1.8234   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    0.6241    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.0776    1.4950 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
  4  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  8  3  1  0  0  0  0
 16 11  1  0  0  0  0
 17  7  1  0  0  0  0
 24 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 21 33  1  0  0  0  0
 21 34  1  0  0  0  0
 22 35  1  1  0  0  0
 23 36  1  0  0  0  0
 23 37  1  0  0  0  0
 23 38  1  0  0  0  0
 24 39  1  0  0  0  0
 24 40  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    5.8139   -1.4356    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -1.2079    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -0.1580   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.7238   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.7709   -1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029    1.9429   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    1.0467   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.0040   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.9306    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8947    1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.7733    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.6415    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.5345    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.4982    1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    0.4086    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.2821    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.2231   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.1660   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    1.5309   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    2.6468   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6986    1.2927   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664    0.2017   -0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4793   -1.0167   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2295    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3544   -0.4810    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -2.2081    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165   -1.7479   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520    0.5787   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328    2.4794   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    2.7497   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323   -2.4712    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -2.1905    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.0731   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2678    2.2426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.5231   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.4182   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427   -0.7723   -2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -1.8234   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    0.6241    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.0776    1.4950 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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  2  0
 16 17  1  0
 17 18  2  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
  8  3  1  0
 16 11  1  0
 17  7  1  0
 24 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
 12 31  1  0
 13 32  1  0
 21 33  1  0
 21 34  1  0
 22 35  1  1
 23 36  1  0
 23 37  1  0
 23 38  1  0
 24 39  1  0
 24 40  1  0
M  END


  Mrv1652306242107383D          

 40 43  0  0  0  0            999 V2000
    5.8139   -1.4356    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -1.2079    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -0.1580   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.7238   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.7709   -1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029    1.9429   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    1.0467   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.0040   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.9306    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8947    1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.7733    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.6415    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.5345    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.4982    1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    0.4086    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.2821    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.2231   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.1660   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    1.5309   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    2.6468   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6986    1.2927   -0.9212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4664    0.2017   -0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4793   -1.0167   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2295    1.0763 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3544   -0.4810    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -2.2081    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165   -1.7479   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520    0.5787   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328    2.4794   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    2.7497   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323   -2.4712    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -2.1905    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.0731   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2678    2.2426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.5231   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.4182   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427   -0.7723   -2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -1.8234   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    0.6241    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.0776    1.4950 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
  4  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  8  3  1  0  0  0  0
 16 11  1  0  0  0  0
 17  7  1  0  0  0  0
 24 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 21 33  1  0  0  0  0
 21 34  1  0  0  0  0
 22 35  1  1  0  0  0
 23 36  1  0  0  0  0
 23 37  1  0  0  0  0
 23 38  1  0  0  0  0
 24 39  1  0  0  0  0
 24 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(C(OC([H])([H])[H])=C1[H])C(=O)C1=C([H])C([H])=C3C(C(=O)C([H])([H])[C@@]([H])(C([H])([H])[H])C3([H])[H])=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O4/c1-10-8-11-6-7-13-18(16(11)14(21)9-10)20(23)12-4-3-5-15(24-2)17(12)19(13)22/h3-7,10H,8-9H2,1-2H3/t10-/m0/s1

> <INCHI_KEY>
ZUCWNLVDTXGGSU-JTQLQIEISA-N

> <FORMULA>
C20H16O4

> <MOLECULAR_WEIGHT>
320.344

> <EXACT_MASS>
320.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.20672420435011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-8-methoxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.3559327576666664

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.519780553694766

> <JCHEM_PKA_STRONGEST_BASIC>
-4.879959956499247

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
90.43149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-8-methoxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    5.8139   -1.4356    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -1.2079    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -0.1580   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.7238   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.7709   -1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029    1.9429   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    1.0467   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.0040   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.9306    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8947    1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.7733    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.6415    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.5345    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.4982    1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    0.4086    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.2821    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.2231   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.1660   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    1.5309   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    2.6468   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6986    1.2927   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664    0.2017   -0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4793   -1.0167   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2295    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3544   -0.4810    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -2.2081    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165   -1.7479   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520    0.5787   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328    2.4794   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    2.7497   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323   -2.4712    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -2.1905    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.0731   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2678    2.2426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.5231   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.4182   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427   -0.7723   -2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -1.8234   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    0.6241    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.0776    1.4950 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
  4  5  1  0
  5  6  2  0
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  8  3  1  0
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 17  7  1  0
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 22 35  1  1
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 23 38  1  0
 24 39  1  0
 24 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.814  -1.436   0.476  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.436  -1.208   0.521  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.846  -0.158  -0.158  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.581   0.724  -0.917  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.980   1.771  -1.591  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.603   1.943  -1.506  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.890   1.047  -0.740  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.495   0.004  -0.069  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.723  -0.931   0.736  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.253  -1.895   1.358  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.289  -0.773   0.845  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.477  -1.642   1.592  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.841  -1.535   1.721  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.445  -0.498   1.062  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.676   0.409   0.288  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.313   0.282   0.167  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.428   1.223  -0.642  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.063   2.166  -1.266  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.373   1.531  -0.313  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.884   2.647  -0.315  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.699   1.293  -0.921  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.466   0.202  -0.241  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.479  -1.017  -1.135  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.890  -0.230   1.076  0.00  0.00           C+0
HETATM   25  H   UNK     0       6.354  -0.481   0.733  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.123  -2.208   1.186  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.117  -1.748  -0.546  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.652   0.579  -0.975  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.533   2.479  -2.195  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.104   2.750  -2.020  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.032  -2.471   2.117  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.474  -2.191   2.292  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.602   1.073  -2.007  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.268   2.243  -0.849  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.512   0.523  -0.098  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.432  -1.418  -1.124  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.743  -0.772  -2.179  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.109  -1.823  -0.715  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.050   0.624   1.793  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.456  -1.078   1.495  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   11                                                  
CONECT   17   16   18    7                                                  
CONECT   18   17                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33   34                                             
CONECT   22   21   23   24   35                                             
CONECT   23   22   36   37   38                                             
CONECT   24   22   14   39   40                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   21                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
CONECT   37   23                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   24                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

RDKit          3D

40 43  0  0  0  0  0  0  0  0999 V2000
    5.8139   -1.4356    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -1.2079    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -0.1580   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.7238   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.7709   -1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029    1.9429   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    1.0467   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.0040   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.9306    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -1.8947    1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.7733    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -1.6415    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.5345    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.4982    1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    0.4086    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.2821    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.2231   -0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    2.1660   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734    1.5309   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    2.6468   -0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6986    1.2927   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664    0.2017   -0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4793   -1.0167   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.2295    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3544   -0.4810    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1229   -2.2081    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165   -1.7479   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6520    0.5787   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5328    2.4794   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    2.7497   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0323   -2.4712    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -2.1905    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.0731   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2678    2.2426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.5231   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.4182   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427   -0.7723   -2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -1.8234   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0503    0.6241    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -1.0776    1.4950 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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  2  0
 16 17  1  0
 17 18  2  0
 15 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
  8  3  1  0
 16 11  1  0
 17  7  1  0
 24 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
 12 31  1  0
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 21 33  1  0
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 22 35  1  1
 23 36  1  0
 23 37  1  0
 23 38  1  0
 24 39  1  0
 24 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₄

Average Mass

320.3440 Da

Monoisotopic Mass

320.10486 Da

IUPAC Name

(3S)-8-methoxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

(3S)-8-methoxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(=O)C1=C(C2=O)C2=C(C[C@H](C)CC2=O)C=C1

InChI Identifier

InChI=1S/C20H16O4/c1-10-8-11-6-7-13-18(16(11)14(21)9-10)20(23)12-4-3-5-15(24-2)17(12)19(13)22/h3-7,10H,8-9H2,1-2H3/t10-/m0/s1

InChI Key

ZUCWNLVDTXGGSU-JTQLQIEISA-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 griseorubiginosus	NPAtlas	2211364

Species Where Detected

Species Name	Source	Reference
Streptomyces griseorubiginosus No.Q144-2	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Anthracene
Phenanthrene
Tetralin
Phenol ether
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Ketone
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	3.69	ALOGPS
logP	3.36	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.52	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	34.21 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

NPAtlas ID

NPA013535

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9133395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10958178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Boonlarppradab C, Suriyachadkun C, Rachtawee P, Choowong W: Saccharosporones A, B and C, cytotoxic antimalarial angucyclinones from Saccharopolyspora sp. BCC 21906. J Antibiot (Tokyo). 2013 Jun;66(6):305-9. doi: 10.1038/ja.2013.16. Epub 2013 Apr 3. [PubMed:23549355 ]
Kesenheimer C, Kalogerakis A, Meissner A, Groth U: The cobalt way to angucyclinones: asymmetric total synthesis of the antibiotics (+)-rubiginone B2, (-)-tetrangomycin, and (-)-8-O-methyltetrangomycin. Chemistry. 2010 Aug 2;16(29):8805-21. doi: 10.1002/chem.201000804. [PubMed:20575121 ]
Kaliappan KP, Ravikumar V: Angucyclinone antibiotics: total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755. J Org Chem. 2007 Aug 3;72(16):6116-26. doi: 10.1021/jo070709p. Epub 2007 Jul 11. [PubMed:17625884 ]
Sato K, Asao N, Yamamoto Y: Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2. J Org Chem. 2005 Oct 28;70(22):8977-81. doi: 10.1021/jo051444m. [PubMed:16238336 ]

Showing NP-Card for Rubiginone B2 (NP0010484)

MOL for NP0010484 (Rubiginone B2)

3D MOL for NP0010484 (Rubiginone B2)

3D SDF for NP0010484 (Rubiginone B2)

3D-SDF for NP0010484 (Rubiginone B2)

PDB for NP0010484 (Rubiginone B2)

3D PDB for NP0010484 (Rubiginone B2)

SMILES for NP0010484 (Rubiginone B2)

INCHI for NP0010484 (Rubiginone B2)

Structure for NP0010484 (Rubiginone B2)

3D Structure for NP0010484 (Rubiginone B2)