NP-MRD: Showing NP-Card for 6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B (NP0013233)

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Record Information

Version

1.0

Created at

2021-01-05 22:39:43 UTC

Updated at

2021-07-15 17:13:55 UTC

NP-MRD ID

NP0013233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B

Provided By

NPAtlas

Description

6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B is found in Streptomyces. It was first documented in 2014 (PMID: 25153802).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119343D          

 71 76  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
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 33 66  1  0
 36 67  1  0
 37 68  1  6
 38 69  1  0
 38 70  1  0
 38 71  1  0
M  END


  Mrv1652306242119343D          

 71 76  0  0  0  0            999 V2000
    5.0157    2.4741   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821    1.5382    1.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6400    0.9747    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   -0.0428    0.9747 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6283   -0.3659    1.5222 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5422    0.7810    1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7144    0.5914    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1793    2.0151    1.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -1.2668    0.9604 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0175   -0.8465    0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -1.8011    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.4210   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.0840   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.8871    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    2.1990    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822    0.4739    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    0.3522   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129    1.5240   -0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164   -0.6631   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778   -1.9466   -1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -2.4206   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548   -3.6321   -0.9704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304   -2.8492   -1.8982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6580   -2.6602   -0.9936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0186   -1.2151   -0.9162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0259   -0.7221    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -0.2136    0.7528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6844   -0.9799    2.0044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8297   -0.3202    2.7064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3117    0.9281    2.0100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2417    0.5928    1.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2013    1.7797    1.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7074    2.5420    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    1.1033    1.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.3923   -1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4596    0.9143   -1.7876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839   -1.0452   -3.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4411   -0.2782   -4.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630   -2.3429   -3.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    1.9528   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.1599    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    3.1560   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    2.1778    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.3348   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4724   -0.7779    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0601   -1.1414    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8060    2.7903    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -1.9341    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -1.7806    1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -2.8320   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    2.7864   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358   -3.8871   -2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960   -2.9975    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646   -3.2788   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0415   -1.0632   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9940   -0.3089   -0.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948   -2.0506    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7745   -0.9974    2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6879   -1.0403    2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -0.1656    3.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654    1.5254    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8385    1.3659    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133    2.5683    2.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8785    3.1455   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    3.2543    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0276    1.8320   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    1.4202   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757   -1.0493   -3.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    0.0691   -5.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    0.5535   -3.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.9492   -4.7475 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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 16  2  1  0  0  0  0
 35 19  1  0  0  0  0
 16 10  1  0  0  0  0
 39 23  1  0  0  0  0
 21 12  1  0  0  0  0
 34 27  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  2 43  1  1  0  0  0
  4 44  1  6  0  0  0
  5 45  1  0  0  0  0
  5 46  1  0  0  0  0
  8 47  1  0  0  0  0
  9 48  1  0  0  0  0
  9 49  1  0  0  0  0
 11 50  1  0  0  0  0
 15 51  1  0  0  0  0
 23 52  1  6  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 25 55  1  6  0  0  0
 27 56  1  6  0  0  0
 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
 30 61  1  1  0  0  0
 31 62  1  0  0  0  0
 32 63  1  1  0  0  0
 33 64  1  0  0  0  0
 33 65  1  0  0  0  0
 33 66  1  0  0  0  0
 36 67  1  0  0  0  0
 37 68  1  6  0  0  0
 38 69  1  0  0  0  0
 38 70  1  0  0  0  0
 38 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])O[C@]([H])(C2=C(O[H])C3=C(C([H])=C2C1([H])[H])C(=O)C1=C(C3=O)[C@@]2(O[H])[C@]([H])(O[C@]1([H])C([H])([H])[C@@]2([H])O[C@]1([H])O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O11/c1-10-16(29)4-5-20(37-10)39-18-9-17-23-24(28(18,35)12(3)38-17)27(34)22-15(25(23)32)7-13-6-14(8-19(30)31)36-11(2)21(13)26(22)33/h7,10-12,14,16-18,20,29,33,35H,4-6,8-9H2,1-3H3,(H,30,31)/t10-,11-,12+,14+,16-,17+,18+,20-,28+/m0/s1

> <INCHI_KEY>
ZJPBUJSZARGKRN-LOYGLLJSSA-N

> <FORMULA>
C28H32O11

> <MOLECULAR_WEIGHT>
544.553

> <EXACT_MASS>
544.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.511150428813814

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,7S,9R,16R,18R,19R)-1,5-dihydroxy-19-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),4,6(11),12-tetraen-9-yl]acetic acid

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.2522591176666666

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.704990981262023

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3994433496278718

> <JCHEM_PKA_STRONGEST_BASIC>
-3.150846787141564

> <JCHEM_POLAR_SURFACE_AREA>
169.05

> <JCHEM_REFRACTIVITY>
134.0323

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,7S,9R,16R,18R,19R)-1,5-dihydroxy-19-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),4,6(11),12-tetraen-9-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
    5.0157    2.4741   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821    1.5382    1.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6400    0.9747    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   -0.0428    0.9747 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6283   -0.3659    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5422    0.7810    1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7144    0.5914    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1793    2.0151    1.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -1.2668    0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -0.8465    0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -1.8011    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.4210   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.0840   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.8871    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    2.1990    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822    0.4739    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    0.3522   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129    1.5240   -0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164   -0.6631   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778   -1.9466   -1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -2.4206   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548   -3.6321   -0.9704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304   -2.8492   -1.8982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6580   -2.6602   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.2151   -0.9162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0259   -0.7221    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746   -0.2136    0.7528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6844   -0.9799    2.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8297   -0.3202    2.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3117    0.9281    2.0100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2417    0.5928    1.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2013    1.7797    1.4873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7074    2.5420    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    1.1033    1.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.3923   -1.8062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4596    0.9143   -1.7876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839   -1.0452   -3.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4411   -0.2782   -4.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630   -2.3429   -3.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    1.9528   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.1599    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    3.1560   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    2.1778    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.3348   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4724   -0.7779    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0601   -1.1414    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8060    2.7903    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -1.9341    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -1.7806    1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -2.8320   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    2.7864   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358   -3.8871   -2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960   -2.9975    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646   -3.2788   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0415   -1.0632   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9940   -0.3089   -0.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8948   -2.0506    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7745   -0.9974    2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6879   -1.0403    2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -0.1656    3.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654    1.5254    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8385    1.3659    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133    2.5683    2.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8785    3.1455   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    3.2543    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0276    1.8320   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    1.4202   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757   -1.0493   -3.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    0.0691   -5.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    0.5535   -3.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.9492   -4.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 25 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 37 39  1  0
 16  2  1  0
 35 19  1  0
 16 10  1  0
 39 23  1  0
 21 12  1  0
 34 27  1  0
  1 40  1  0
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  4 44  1  6
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  8 47  1  0
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 11 50  1  0
 15 51  1  0
 23 52  1  6
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 29 60  1  0
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 32 63  1  1
 33 64  1  0
 33 65  1  0
 33 66  1  0
 36 67  1  0
 37 68  1  6
 38 69  1  0
 38 70  1  0
 38 71  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       5.016   2.474  -0.061  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.582   1.538   1.046  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.640   0.975   1.721  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.252  -0.043   0.975  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.628  -0.366   1.522  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.542   0.781   1.500  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.714   0.591   1.945  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.179   2.015   1.026  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.367  -1.267   0.960  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.018  -0.847   0.493  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.124  -1.801   0.012  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.884  -1.421  -0.415  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.520  -0.084  -0.366  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.403   0.887   0.113  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.099   2.199   0.181  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.682   0.474   0.550  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.185   0.352  -0.821  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.213   1.524  -0.810  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.716  -0.663  -1.314  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.378  -1.947  -1.364  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.922  -2.421  -0.928  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.255  -3.632  -0.970  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.430  -2.849  -1.898  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.658  -2.660  -0.994  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.019  -1.215  -0.916  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.026  -0.722   0.386  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.275  -0.214   0.753  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.684  -0.980   2.004  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.830  -0.320   2.706  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.312   0.928   2.010  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.242   0.593   1.018  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.201   1.780   1.487  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.707   2.542   0.281  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.064   1.103   1.150  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.089  -0.392  -1.806  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.460   0.914  -1.788  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.184  -1.045  -3.172  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.441  -0.278  -4.231  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.763  -2.343  -3.152  0.00  0.00           O+0
HETATM   40  H   UNK     0       5.428   1.953  -0.938  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.781   3.160   0.364  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.160   3.156  -0.335  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.023   2.178   1.789  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.307   0.335  -0.067  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.472  -0.778   2.550  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.060  -1.141   0.838  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.806   2.790   1.079  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.778  -1.934   0.160  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.332  -1.781   1.932  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.401  -2.832  -0.027  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.358   2.786  -0.023  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.136  -3.887  -2.001  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.396  -2.998   0.034  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.465  -3.279  -1.438  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.042  -1.063  -1.316  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.994  -0.309  -0.065  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.895  -2.051   1.766  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.775  -0.997   2.655  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.688  -1.040   2.711  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.558  -0.166   3.759  0.00  0.00           H+0
HETATM   61  H   UNK     0      -6.865   1.525   2.770  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.838   1.366   0.855  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.913   2.568   2.241  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.878   3.146  -0.151  0.00  0.00           H+0
HETATM   65  H   UNK     0      -6.520   3.254   0.570  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.028   1.832  -0.505  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.271   1.420  -2.614  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.276  -1.049  -3.428  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.140   0.069  -5.023  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.835   0.554  -3.817  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.714  -0.949  -4.747  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3   16   43                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9   44                                             
CONECT    5    4    6   45   46                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   47                                                       
CONECT    9    4   10   48   49                                             
CONECT   10    9   11   16                                                  
CONECT   11   10   12   50                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   51                                                       
CONECT   16   14    2   10                                                  
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   35                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22   12                                                  
CONECT   22   21                                                            
CONECT   23   20   24   39   52                                             
CONECT   24   23   25   53   54                                             
CONECT   25   24   26   35   55                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   34   56                                             
CONECT   28   27   29   57   58                                             
CONECT   29   28   30   59   60                                             
CONECT   30   29   31   32   61                                             
CONECT   31   30   62                                                       
CONECT   32   30   33   34   63                                             
CONECT   33   32   64   65   66                                             
CONECT   34   32   27                                                       
CONECT   35   25   36   37   19                                             
CONECT   36   35   67                                                       
CONECT   37   35   38   39   68                                             
CONECT   38   37   69   70   71                                             
CONECT   39   37   23                                                       
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    2                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    5                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49    9                                                            
CONECT   50   11                                                            
CONECT   51   15                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   31                                                            
CONECT   63   32                                                            
CONECT   64   33                                                            
CONECT   65   33                                                            
CONECT   66   33                                                            
CONECT   67   36                                                            
CONECT   68   37                                                            
CONECT   69   38                                                            
CONECT   70   38                                                            
CONECT   71   38                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  152    0
END

RDKit          3D

71 76  0  0  0  0  0  0  0  0999 V2000
    5.0157    2.4741   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821    1.5382    1.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6400    0.9747    1.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   -0.0428    0.9747 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6283   -0.3659    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5422    0.7810    1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7144    0.5914    1.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1793    2.0151    1.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -1.2668    0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -0.8465    0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -1.8011    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -1.4210   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.0840   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.8871    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    2.1990    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822    0.4739    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9218   -2.4206   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7630   -2.3429   -3.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    1.9528   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.1599    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602    3.1560   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    2.1778    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074    0.3348   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4724   -0.7779    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0601   -1.1414    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8060    2.7903    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7780   -1.9341    0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322   -1.7806    1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -2.8320   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8948   -2.0506    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7745   -0.9974    2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6879   -1.0403    2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -0.1656    3.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654    1.5254    2.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8385    1.3659    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133    2.5683    2.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8785    3.1455   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    3.2543    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0276    1.8320   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    1.4202   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757   -1.0493   -3.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    0.0691   -5.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    0.5535   -3.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.9492   -4.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 25 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 37 39  1  0
 16  2  1  0
 35 19  1  0
 16 10  1  0
 39 23  1  0
 21 12  1  0
 34 27  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  1
  4 44  1  6
  5 45  1  0
  5 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 11 50  1  0
 15 51  1  0
 23 52  1  6
 24 53  1  0
 24 54  1  0
 25 55  1  6
 27 56  1  6
 28 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  1
 31 62  1  0
 32 63  1  1
 33 64  1  0
 33 65  1  0
 33 66  1  0
 36 67  1  0
 37 68  1  6
 38 69  1  0
 38 70  1  0
 38 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₁

Average Mass

544.5530 Da

Monoisotopic Mass

544.19446 Da

IUPAC Name

2-[(1R,7S,9R,16R,18R,19R)-1,5-dihydroxy-19-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),4,6(11),12-tetraen-9-yl]acetic acid

Traditional Name

[(1R,7S,9R,16R,18R,19R)-1,5-dihydroxy-19-{[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy}-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),4,6(11),12-tetraen-9-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](CC[C@@H]1O)O[C@@H]1C[C@H]2O[C@H](C)[C@]1(O)C1=C2C(=O)C2=CC3=C([C@H](C)O[C@@H](CC(O)=O)C3)C(O)=C2C1=O

InChI Identifier

InChI=1S/C28H32O11/c1-10-16(29)4-5-20(37-10)39-18-9-17-23-24(28(18,35)12(3)38-17)27(34)22-15(25(23)32)7-13-6-14(8-19(30)31)36-11(2)21(13)26(22)33/h7,10-12,14,16-18,20,29,33,35H,4-6,8-9H2,1-3H3,(H,30,31)/t10-,11-,12?,14+,16-,17+,18+,20-,28+/m0/s1

InChI Key

ZJPBUJSZARGKRN-LOYGLLJSSA-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	NPAtlas	25153802

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.15	ALOGPS
logP	1.25	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.03 m³·mol⁻¹	ChemAxon
Polarizability	55.51 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Jiang B, Li S, Zhao W, Li T, Zuo L, Nan Y, Wu L, Liu H, Yu L, Shan G, Zuo L: 6-Deoxy-13-hydroxy-8,11-dione-dihydrogranaticin B, an intermediate in granaticin biosynthesis, from Streptomyces sp. CPCC 200532. J Nat Prod. 2014 Sep 26;77(9):2130-3. doi: 10.1021/np500138k. Epub 2014 Aug 25. [PubMed:25153802 ]

Showing NP-Card for 6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B (NP0013233)

MOL for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

3D MOL for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

3D SDF for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

3D-SDF for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

PDB for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

3D PDB for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

SMILES for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

INCHI for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

Structure for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)

3D Structure for NP0013233 (6-deoxy-13-hydroxy-8,11-dionedihydrogranaticin B)