NP-MRD: Showing NP-Card for BE-24566B (NP0023053)

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Record Information

Version

2.0

Created at

2021-01-06 08:11:03 UTC

Updated at

2021-07-15 17:40:42 UTC

NP-MRD ID

NP0023053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

BE-24566B

Provided By

NPAtlas

Description

BE-24566B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. BE-24566B is found in Streptomyces strain A24566 and Streptomyces violaceusniger. BE-24566B was first documented in 1995 (PMID: 8557611). Based on a literature review very few articles have been published on BE-24566B (PMID: 16180833) (PMID: 27248985).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105393D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105393D          

 58 63  0  0  0  0            999 V2000
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   -3.0663   -0.7585   -0.3294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819   -1.2200   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.8951    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.4818   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164    2.8775    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    2.0187    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.1734    2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4239    2.7552   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357    2.7680   -2.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.1936   -3.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -0.2316    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -4.0183    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104   -2.9361   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253   -4.1549   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -3.5857    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -3.5712   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6089    2.0511    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    4.3076    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9927    3.6377   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5286   -0.5020   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1206   -1.4221   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -2.1173   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721   -0.4154   -2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -1.6352    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.8159    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -2.0422    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 11 34  1  0  0  0  0
  8  2  1  0  0  0  0
 20  9  1  0  0  0  0
 30 23  1  0  0  0  0
 34  7  1  0  0  0  0
 20 14  1  0  0  0  0
 31 16  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  5 39  1  0  0  0  0
  6 40  1  0  0  0  0
  9 41  1  1  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 15 47  1  0  0  0  0
 19 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
 28 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
 33 57  1  0  0  0  0
 33 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=C1[H])C([H])([H])[H])[C@]1([H])O[C@@](O2)(C([H])([H])[H])C([H])([H])C2=C([H])C3=C(C(=O)C4=C(O[H])C([H])=C(O[H])C([H])=C4C3(C([H])([H])[H])C([H])([H])[H])C(O[H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O7/c1-11-5-13(28)9-18-19(11)25-20-12(10-27(4,33-18)34-25)6-15-22(23(20)31)24(32)21-16(26(15,2)3)7-14(29)8-17(21)30/h5-9,25,28-31H,10H2,1-4H3/t25-,27-/m0/s1

> <INCHI_KEY>
MDUGEFRGUDVHQH-UHFFFAOYSA-N

> <FORMULA>
C27H24O7

> <MOLECULAR_WEIGHT>
460.482

> <EXACT_MASS>
460.152203113

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
48.51701810664657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,17R)-3,7,9,21-tetrahydroxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19(24),20,22-nonaen-5-one

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
6.453321934333332

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.39145632894062

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.710390296872088

> <JCHEM_PKA_STRONGEST_BASIC>
-4.328756634414084

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
136.3191

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,17R)-3,7,9,21-tetrahydroxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19(24),20,22-nonaen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
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   -0.8431   -1.7790   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0088    2.8300    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5676    4.0317    0.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3612    2.7634   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8111    0.4835   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663   -0.7585   -0.3294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819   -1.2200   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.8951    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.4818   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3876    2.0187    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.1734    2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4239    2.7552   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357    2.7680   -2.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.1936   -3.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -0.2316    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -4.0183    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104   -2.9361   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253   -4.1549   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -3.5857    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -3.5712   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402   -2.7337   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    2.0511    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    4.3076    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9927    3.6377   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9047    1.2659   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5286   -0.5020   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1206   -1.4221   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -2.1173   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1638   -2.8159    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -2.0422    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
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 18 19  1  0
 18 20  2  0
 17 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 11 34  1  0
  8  2  1  0
 20  9  1  0
 30 23  1  0
 34  7  1  0
 20 14  1  0
 31 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  5 39  1  0
  6 40  1  0
  9 41  1  1
 12 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 15 47  1  0
 19 48  1  0
 25 49  1  0
 26 50  1  0
 28 51  1  0
 29 52  1  0
 32 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  0
 33 57  1  0
 33 58  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       4.280   1.879   1.831  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.109   1.296   0.470  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.812   1.870  -0.602  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.775   1.378  -1.882  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.469   1.949  -2.936  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.997   0.242  -2.132  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.311  -0.331  -1.122  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.361   0.193   0.178  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.521  -0.545   1.144  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.039  -1.867   1.040  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.679  -2.460  -0.164  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.654  -3.467  -0.649  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.287  -3.046   0.148  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.479  -1.762   0.287  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.843  -1.779  -0.054  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.653  -0.661   0.044  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.068   0.482   0.503  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.288   0.553   0.868  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.768   1.753   1.321  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.075  -0.611   0.751  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.850   1.732   0.624  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.315   2.770   1.043  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.256   1.656   0.225  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.009   2.830   0.315  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.568   4.032   0.750  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.361   2.763  -0.086  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.908   1.592  -0.543  0.00  0.00           C+0
HETATM   28  O   UNK     0      -7.248   1.512  -0.945  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.164   0.441  -0.629  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.811   0.484  -0.234  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.066  -0.759  -0.329  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.082  -1.220  -1.800  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.729  -1.895   0.440  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.501  -1.482  -1.224  0.00  0.00           O+0
HETATM   35  H   UNK     0       3.816   2.878   1.944  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.388   2.019   1.991  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.978   1.173   2.621  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.424   2.755  -0.420  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.036   2.768  -2.776  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.932  -0.194  -3.137  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.635  -0.232   2.191  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.160  -4.018   0.169  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.410  -2.936  -1.284  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.125  -4.155  -1.349  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.356  -3.586   1.087  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.862  -3.571  -0.708  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.240  -2.734  -0.417  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.609   2.051   1.633  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.707   4.308   1.067  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.993   3.638  -0.039  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.905   1.266  -0.212  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.529  -0.502  -0.979  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.121  -1.422  -2.134  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.448  -2.117  -1.940  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.672  -0.415  -2.438  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.688  -1.635   1.517  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.164  -2.816   0.193  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.738  -2.042   0.053  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   39                                                       
CONECT    6    4    7   40                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   10   20   41                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13   34                                             
CONECT   12   11   42   43   44                                             
CONECT   13   11   14   45   46                                             
CONECT   14   13   15   20                                                  
CONECT   15   14   16   47                                                  
CONECT   16   15   17   31                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   48                                                       
CONECT   20   18    9   14                                                  
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   49                                                       
CONECT   26   24   27   50                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   51                                                       
CONECT   29   27   30   52                                                  
CONECT   30   29   31   23                                                  
CONECT   31   30   32   33   16                                             
CONECT   32   31   53   54   55                                             
CONECT   33   31   56   57   58                                             
CONECT   34   11    7                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    9                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   15                                                            
CONECT   48   19                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   28                                                            
CONECT   52   29                                                            
CONECT   53   32                                                            
CONECT   54   32                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   33                                                            
CONECT   58   33                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

RDKit          3D

58 63  0  0  0  0  0  0  0  0999 V2000
    4.2802    1.8785    1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1092    1.2960    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8117    1.8696   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751    1.3777   -1.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4690    1.9489   -2.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9968    0.2422   -2.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -0.3311   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607    0.1931    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -0.5452    1.1439 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0387   -1.8671    1.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -2.4603   -0.1637 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6536   -3.4670   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -3.0459    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -1.7615    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -1.7790   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -0.6610    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0677    0.4815    0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.5525    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    1.7534    1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -0.6114    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    1.7322    0.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149    2.7703    1.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558    1.6555    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088    2.8300    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5676    4.0317    0.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3612    2.7634   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9078    1.5923   -0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2485    1.5117   -0.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1642    0.4411   -0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8111    0.4835   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663   -0.7585   -0.3294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819   -1.2200   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.8951    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.4818   -1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164    2.8775    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    2.0187    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.1734    2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4239    2.7552   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357    2.7680   -2.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.1936   -3.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -0.2316    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -4.0183    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4104   -2.9361   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253   -4.1549   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -3.5857    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -3.5712   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402   -2.7337   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    2.0511    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    4.3076    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9927    3.6377   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9047    1.2659   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5286   -0.5020   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1206   -1.4221   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -2.1173   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721   -0.4154   -2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -1.6352    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.8159    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -2.0422    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 11 34  1  0
  8  2  1  0
 20  9  1  0
 30 23  1  0
 34  7  1  0
 20 14  1  0
 31 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  5 39  1  0
  6 40  1  0
  9 41  1  1
 12 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 15 47  1  0
 19 48  1  0
 25 49  1  0
 26 50  1  0
 28 51  1  0
 29 52  1  0
 32 53  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  0
 33 57  1  0
 33 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₇

Average Mass

460.4820 Da

Monoisotopic Mass

460.15220 Da

IUPAC Name

(1R,17R)-3,7,9,21-tetrahydroxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19(24),20,22-nonaen-5-one

Traditional Name

(1R,17R)-3,7,9,21-tetrahydroxy-12,12,17,23-tetramethyl-18,25-dioxahexacyclo[15.7.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{19,24}]pentacosa-2,4(13),6,8,10,14,19(24),20,22-nonaen-5-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1C1OC(C)(CC3=C1C(O)=C1C(=O)C4=C(O)C=C(O)C=C4C(C)(C)C1=C3)O2

InChI Identifier

InChI=1S/C27H24O7/c1-11-5-13(28)9-18-19(11)25-20-12(10-27(4,33-18)34-25)6-15-22(23(20)31)24(32)21-16(26(15,2)3)7-14(29)8-17(21)30/h5-9,25,28-31H,10H2,1-4H3

InChI Key

MDUGEFRGUDVHQH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces strain A24566	Bacteria	KNApSAcK
Streptomyces violaceusniger	NPAtlas	8557611

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Anthracene
Benzopyran
Isochromane
2-benzopyran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Pyran
Benzenoid
Vinylogous acid
Ketone
Polyol
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.22	ALOGPS
logP	6.45	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	136.32 m³·mol⁻¹	ChemAxon
Polarizability	48.52 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

NPA001814

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8044556

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9868865

PDB ID

Not Available

ChEBI ID

65474

Good Scents ID

Not Available

References

General References

Herath KB, Jayasuriya H, Guan Z, Schulman M, Ruby C, Sharma N, MacNaul K, Menke JG, Kodali S, Galgoci A, Wang J, Singh SB: Anthrabenzoxocinones from Streptomyces sp. as liver X receptor ligands and antibacterial agents. J Nat Prod. 2005 Sep;68(9):1437-40. doi: 10.1021/np050176k. [PubMed:16180833 ]
Kojiri K, Nakajima S, Fuse A, Suzuki H, Suda H: BE-24566B, a new antibiotic produced by Streptomyces violaceusniger. J Antibiot (Tokyo). 1995 Dec;48(12):1506-8. doi: 10.7164/antibiotics.48.1506. [PubMed:8557611 ]
Lu Y, Yue C, Shao M, Qian S, Liu N, Bao Y, Wang M, Liu M, Li X, Wang Y, Huang Y: Molecular Genetic Characterization of an Anthrabenzoxocinones Gene Cluster in Streptomyces Sp. FJS31-2 for the Biosynthesis of BE-24566B and Zunyimycin Ale. Molecules. 2016 May 30;21(6). pii: molecules21060711. doi: 10.3390/molecules21060711. [PubMed:27248985 ]

Showing NP-Card for BE-24566B (NP0023053)

MOL for NP0023053 (BE-24566B)

3D MOL for NP0023053 (BE-24566B)

3D SDF for NP0023053 (BE-24566B)

3D-SDF for NP0023053 (BE-24566B)

PDB for NP0023053 (BE-24566B)

3D PDB for NP0023053 (BE-24566B)

SMILES for NP0023053 (BE-24566B)

INCHI for NP0023053 (BE-24566B)

Structure for NP0023053 (BE-24566B)

3D Structure for NP0023053 (BE-24566B)