NP-MRD: Showing NP-Card for JBIR-85 (NP0010504)

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Record Information

Version

2.0

Created at

2021-01-05 20:00:07 UTC

Updated at

2021-07-15 17:06:17 UTC

NP-MRD ID

NP0010504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

JBIR-85

Provided By

NPAtlas

Description

JBIR-85 belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. JBIR-85 is found in Streptomyces sp. RI-77. JBIR-85 was first documented in 2011 (PMID: 22145663). Based on a literature review very few articles have been published on JBIR-85.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107383D          

 52 56  0  0  0  0            999 V2000
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   -5.5839   -0.6841    0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -0.0398    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137    1.2995   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433    1.9216   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    3.2766   -0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252    1.1304    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   -0.2420    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.8623    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242107383D          

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    2.5751   -0.0418   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -0.4265   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -3.5562    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -4.4260   -1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -4.2390   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645    3.2165    2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    3.5016    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    3.0631    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    3.5889    0.3740 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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
  9  3  1  0  0  0  0
 18 13  1  0  0  0  0
 31  7  1  0  0  0  0
 30 13  1  0  0  0  0
 25 15  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  4 36  1  0  0  0  0
  6 37  1  0  0  0  0
 10 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 15 41  1  1  0  0  0
 16 42  1  1  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 18 45  1  6  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 32 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[H])=C3C(=O)[C@]4(OC([H])([H])[H])C(=O)O[C@]5([H])C([H])([H])[C@@]([H])(C(=O)C([H])([H])[H])[C@@]3(C(=O)C2=C(O[H])C(OC([H])([H])[H])=C1[H])C([H])([H])[C@]45[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O10/c1-7(23)8-4-11-9-6-21(8)15(19(28)22(9,31-3)20(29)32-11)17(26)13-10(24)5-12(30-2)16(25)14(13)18(21)27/h5,8-9,11,24-26H,4,6H2,1-3H3/t8-,9-,11+,21-,22-/m0/s1

> <INCHI_KEY>
IUTSIXZLCRUCRS-AHIRLFQDSA-N

> <FORMULA>
C22H20O10

> <MOLECULAR_WEIGHT>
444.392

> <EXACT_MASS>
444.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.90401913091884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,15R,17R,19S)-17-acetyl-4,7,9-trihydroxy-5,12-dimethoxy-14-oxapentacyclo[10.5.2.0^{1,10}.0^{3,8}.0^{15,19}]nonadeca-3(8),4,6,9-tetraene-2,11,13-trione

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.0819193289999995

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.37048255796051

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.06085325032109

> <JCHEM_PKA_STRONGEST_BASIC>
-4.179150827820961

> <JCHEM_POLAR_SURFACE_AREA>
156.66

> <JCHEM_REFRACTIVITY>
106.79389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,15R,17R,19S)-17-acetyl-4,7,9-trihydroxy-5,12-dimethoxy-14-oxapentacyclo[10.5.2.0^{1,10}.0^{3,8}.0^{15,19}]nonadeca-3(8),4,6,9-tetraene-2,11,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -6.8068    0.0292    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -0.6841    0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -0.0398    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137    1.2995   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433    1.9216   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    3.2766   -0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252    1.1304    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   -0.2420    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.8623    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4222   -2.2004    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743   -1.0260    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -2.1287    1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608   -0.5739    0.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5527   -0.8688    1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.5894    0.7822 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2925   -1.3176   -0.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3397   -1.0204   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848   -1.1175   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3843   -2.4706   -1.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662   -3.7043   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -2.6819   -2.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.6525   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2223    0.6958   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761    1.6294   -1.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    0.8514    0.3684 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6237    1.5277    1.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    2.8614    1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532    1.4863   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    2.5879   -0.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.9227   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895    1.6745   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    3.0408   -0.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6738    0.7718   -0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9739    0.5816    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554   -0.6334   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024    1.9139   -0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2016    3.8822   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315   -2.9629    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.8330    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3127   -0.1199    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789   -0.8544    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -2.4002   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184   -1.7813   -2.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751   -0.0418   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -0.4265   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -3.5562    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -4.4260   -1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -4.2390   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645    3.2165    2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    3.5016    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    3.0631    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    3.5889    0.3740 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 13 11  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 16 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  1
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
  9  3  1  0
 18 13  1  0
 31  7  1  0
 30 13  1  0
 25 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 10 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  1
 16 42  1  1
 17 43  1  0
 17 44  1  0
 18 45  1  6
 20 46  1  0
 20 47  1  0
 20 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 32 52  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      -6.807   0.029   0.096  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.584  -0.684   0.230  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.354  -0.040   0.177  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.214   1.300  -0.003  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.943   1.922  -0.054  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.937   3.277  -0.240  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.825   1.130   0.087  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.998  -0.242   0.275  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.220  -0.862   0.324  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.422  -2.200   0.500  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.774  -1.026   0.521  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.926  -2.129   1.117  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.561  -0.574   0.112  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.553  -0.869   1.206  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.942  -0.589   0.782  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.293  -1.318  -0.497  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.340  -1.020  -1.605  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.885  -1.117  -1.231  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.384  -2.471  -1.539  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.766  -3.704  -0.803  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.419  -2.682  -2.466  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.514  -0.653  -0.816  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.222   0.696  -0.681  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.776   1.629  -1.360  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.176   0.851   0.368  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.624   1.528   1.473  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.900   2.861   1.309  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.953   1.486  -0.146  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.046   2.588  -0.744  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.617   0.923  -0.013  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.490   1.675  -0.049  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.333   3.041  -0.225  0.00  0.00           O+0
HETATM   33  H   UNK     0      -6.674   0.772  -0.730  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.974   0.582   1.041  0.00  0.00           H+0
HETATM   35  H   UNK     0      -7.655  -0.633  -0.075  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.102   1.914  -0.113  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.202   3.882  -0.299  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.832  -2.963   0.608  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.470  -1.833   1.686  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.313  -0.120   2.026  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.679  -0.854   1.543  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.456  -2.400  -0.328  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.518  -1.781  -2.416  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.575  -0.042  -2.072  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.365  -0.427  -1.969  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.394  -3.556   0.069  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.302  -4.426  -1.467  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.158  -4.239  -0.447  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.264   3.216   2.324  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.003   3.502   1.136  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.704   3.063   0.599  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.248   3.589   0.374  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   37                                                       
CONECT    7    5    8   31                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   38                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18   30                                             
CONECT   14   13   15   39   40                                             
CONECT   15   14   16   25   41                                             
CONECT   16   15   17   22   42                                             
CONECT   17   16   18   43   44                                             
CONECT   18   17   19   13   45                                             
CONECT   19   18   20   21                                                  
CONECT   20   19   46   47   48                                             
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28   15                                             
CONECT   26   25   27                                                       
CONECT   27   26   49   50   51                                             
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   13                                                  
CONECT   31   30   32    7                                                  
CONECT   32   31   52                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38   10                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
CONECT   51   27                                                            
CONECT   52   32                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
   -6.8068    0.0292    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -0.6841    0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -0.0398    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137    1.2995   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433    1.9216   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    3.2766   -0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252    1.1304    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   -0.2420    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.8623    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4222   -2.2004    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743   -1.0260    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -2.1287    1.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608   -0.5739    0.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5527   -0.8688    1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.5894    0.7822 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2925   -1.3176   -0.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3397   -1.0204   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848   -1.1175   -1.2310 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3843   -2.4706   -1.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662   -3.7043   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -2.6819   -2.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.6525   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2223    0.6958   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761    1.6294   -1.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    0.8514    0.3684 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6237    1.5277    1.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    2.8614    1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9532    1.4863   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    2.5879   -0.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.9227   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895    1.6745   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    3.0408   -0.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6738    0.7718   -0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9739    0.5816    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554   -0.6334   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024    1.9139   -0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2016    3.8822   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315   -2.9629    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.8330    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3127   -0.1199    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789   -0.8544    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -2.4002   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184   -1.7813   -2.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751   -0.0418   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -0.4265   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -3.5562    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -4.4260   -1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -4.2390   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645    3.2165    2.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030    3.5016    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    3.0631    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2475    3.5889    0.3740 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 13 11  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 16 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  1
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
  9  3  1  0
 18 13  1  0
 31  7  1  0
 30 13  1  0
 25 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 10 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  1
 16 42  1  1
 17 43  1  0
 17 44  1  0
 18 45  1  6
 20 46  1  0
 20 47  1  0
 20 48  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 32 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₀

Average Mass

444.3920 Da

Monoisotopic Mass

444.10565 Da

IUPAC Name

(1S,12S,15R,17R,19S)-17-acetyl-4,7,9-trihydroxy-5,12-dimethoxy-14-oxapentacyclo[10.5.2.0^{1,10}.0^{3,8}.0^{15,19}]nonadeca-3(8),4,6,9-tetraene-2,11,13-trione

Traditional Name

(1S,12S,15R,17R,19S)-17-acetyl-4,7,9-trihydroxy-5,12-dimethoxy-14-oxapentacyclo[10.5.2.0^{1,10}.0^{3,8}.0^{15,19}]nonadeca-3(8),4,6,9-tetraene-2,11,13-trione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(C(O)=C1)C(O)=C1C(=O)[C@@]3(OC)[C@H]4C[C@@]1([C@@H](C[C@H]4OC3=O)C(C)=O)C2=O

InChI Identifier

InChI=1S/C22H20O10/c1-7(23)8-4-11-9-6-21(8)15(19(28)22(9,31-3)20(29)32-11)17(26)13-10(24)5-12(30-2)16(25)14(13)18(21)27/h5,8-9,11,24-26H,4,6H2,1-3H3/t8-,9-,11+,21-,22-/m0/s1

InChI Key

IUTSIXZLCRUCRS-AHIRLFQDSA-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 sp. RI-77	NPAtlas	22145663

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
1-naphthol
Naphthalene
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Gamma butyrolactone
Vinylogous acid
Oxolane
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Ether
Enol
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
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	1.39	ALOGPS
logP	1.08	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	5.06	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.79 m³·mol⁻¹	ChemAxon
Polarizability	41.9 Å³	ChemAxon
Number of Rings	5	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

NPA011316

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441917

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56925680

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Izumikawa M, Satou R, Motohashi K, Nagai A, Ohnishi Y, Takagi M, Shin-ya K: Naphthoquinone-like polyketide isolated from Streptomyces sp. RI-77 and its predicted biosynthetic pathway. J Nat Prod. 2011 Dec 27;74(12):2588-91. doi: 10.1021/np200651e. Epub 2011 Dec 6. [PubMed:22145663 ]

Showing NP-Card for JBIR-85 (NP0010504)

MOL for NP0010504 (JBIR-85)

3D MOL for NP0010504 (JBIR-85)

3D SDF for NP0010504 (JBIR-85)

3D-SDF for NP0010504 (JBIR-85)

PDB for NP0010504 (JBIR-85)

3D PDB for NP0010504 (JBIR-85)

SMILES for NP0010504 (JBIR-85)

INCHI for NP0010504 (JBIR-85)

Structure for NP0010504 (JBIR-85)

3D Structure for NP0010504 (JBIR-85)