NP-MRD: Showing NP-Card for Frenolicin B (NP0022029)

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Record Information

Version

2.0

Created at

2021-01-06 07:15:27 UTC

Updated at

2021-07-15 17:37:56 UTC

NP-MRD ID

NP0022029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Frenolicin B

Provided By

NPAtlas

Description

Frenolicin B 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. Frenolicin B is found in Streptomyces fradiae and Streptomyces roseofulvus. Frenolicin B was first documented in 1978 (PMID: 711620). Based on a literature review very few articles have been published on Frenolicin B (PMID: 23944931) (PMID: 33586974) (PMID: 11739875) (PMID: 32025682) (PMID: 30661989) (PMID: 24151973).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105203D          

 40 43  0  0  0  0            999 V2000
    4.1783   -2.4834   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.4013   -0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0880   -1.1746   -0.4965 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4893   -0.0527    0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2633    1.0432    0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    2.2484   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2319    2.9487    1.2353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3141    3.9996    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    5.1528    1.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    3.4522   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.2680   -0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4686    1.1353   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    0.0633    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -1.0629    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -2.1010    0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9796    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -2.0246    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893   -3.1606    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -1.9209    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588   -0.7954   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    0.2361   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607    0.1466   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.2678   -0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    2.3214   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -3.3639   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -2.8648   -1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.1337   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.6630    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.4566   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.1041   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.8463   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -0.4182    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    2.9318   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.4489    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3154    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    2.3347   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -3.9425    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.7632    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.7306   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.1293   -1.2831 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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13  4  1  0  0  0  0
 22 16  1  0  0  0  0
 11  6  1  0  0  0  0
 23 12  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  1  0  0  0
  6 33  1  6  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 11 36  1  6  0  0  0
 18 37  1  0  0  0  0
 19 38  1  0  0  0  0
 20 39  1  0  0  0  0
 21 40  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    4.1783   -2.4834   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.4013   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.1746   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -0.0527    0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2633    1.0432    0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    2.2484   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2319    2.9487    1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3141    3.9996    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    5.1528    1.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    3.4522   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.2680   -0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4686    1.1353   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    0.0633    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -1.0629    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -2.1010    0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9796    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -2.0246    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893   -3.1606    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -1.9209    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588   -0.7954   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    0.2361   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607    0.1466   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.2678   -0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    2.3214   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -3.3639   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -2.8648   -1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.1337   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.6630    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.4566   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.1041   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.8463   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -0.4182    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    2.9318   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.4489    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3154    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    2.3347   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -3.9425    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.7632    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.7306   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.1293   -1.2831 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
 11 36  1  6
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv1652306242105203D          

 40 43  0  0  0  0            999 V2000
    4.1783   -2.4834   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.4013   -0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0880   -1.1746   -0.4965 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4893   -0.0527    0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2633    1.0432    0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    2.2484   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2319    2.9487    1.2353 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3141    3.9996    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    5.1528    1.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    3.4522   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.2680   -0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4686    1.1353   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    0.0633    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -1.0629    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -2.1010    0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9796    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -2.0246    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893   -3.1606    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -1.9209    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588   -0.7954   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    0.2361   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607    0.1466   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.2678   -0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    2.3214   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -3.3639   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -2.8648   -1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.1337   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.6630    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.4566   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.1041   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.8463   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -0.4182    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    2.9318   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.4489    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3154    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    2.3347   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -3.9425    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.7632    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.7306   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.1293   -1.2831 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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13  4  1  0  0  0  0
 22 16  1  0  0  0  0
 11  6  1  0  0  0  0
 23 12  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  1  0  0  0
  6 33  1  6  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 11 36  1  6  0  0  0
 18 37  1  0  0  0  0
 19 38  1  0  0  0  0
 20 39  1  0  0  0  0
 21 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(C(=O)C2=C([H])C([H])=C1[H])[C@@]1([H])OC(=O)C([H])([H])[C@@]1([H])O[C@]3([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3/t10-,11-,18+/m1/s1

> <INCHI_KEY>
AVCPRTNVVRPELB-YRUZYCQGSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.77974169430551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,15R,17R)-4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.4245802486666665

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.212286959204087

> <JCHEM_PKA_STRONGEST_BASIC>
-4.222703861566388

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
83.38590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,15R,17R)-4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    4.1783   -2.4834   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.4013   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.1746   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -0.0527    0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2633    1.0432    0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    2.2484   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2319    2.9487    1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3141    3.9996    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    5.1528    1.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    3.4522   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.2680   -0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4686    1.1353   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    0.0633    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -1.0629    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -2.1010    0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9796    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -2.0246    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893   -3.1606    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -1.9209    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588   -0.7954   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    0.2361   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607    0.1466   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.2678   -0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    2.3214   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -3.3639   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -2.8648   -1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.1337   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.6630    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.4566   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.1041   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.8463   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -0.4182    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    2.9318   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.4489    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3154    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    2.3347   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -3.9425    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.7632    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.7306   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.1293   -1.2831 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
 11 36  1  6
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.178  -2.483  -0.832  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.523  -1.401  -0.038  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.088  -1.175  -0.497  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.489  -0.053   0.365  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.263   1.043   0.155  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.680   2.248  -0.012  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.232   2.949   1.235  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.314   4.000   0.668  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.121   5.153   1.172  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.237   3.452  -0.460  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.435   2.268  -0.855  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.469   1.135  -0.528  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.067   0.063   0.048  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.815  -1.063   0.382  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.363  -2.101   0.927  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.242  -0.980   0.077  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.103  -2.025   0.378  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.589  -3.161   0.978  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.437  -1.921   0.081  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.959  -0.795  -0.516  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.099   0.236  -0.812  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.761   0.147  -0.521  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.877   1.268  -0.851  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.334   2.321  -1.404  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.488  -3.364  -0.221  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.444  -2.865  -1.576  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.089  -2.134  -1.381  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.508  -1.663   1.045  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.071  -0.457  -0.205  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.524  -2.104  -0.442  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.109  -0.846  -1.557  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.615  -0.418   1.425  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.420   2.932  -0.514  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.099   3.449   1.700  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.656   2.315   1.925  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.643   2.335  -1.924  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.179  -3.942   1.214  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.082  -2.763   0.333  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.013  -0.731  -0.743  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.498   1.129  -1.283  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3   28   29                                             
CONECT    3    2    4   30   31                                             
CONECT    4    3    5   13   32                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   11   33                                             
CONECT    7    6    8   34   35                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12    6   36                                             
CONECT   12   11   13   23                                                  
CONECT   13   12   14    4                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   37                                                       
CONECT   19   17   20   38                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20   22   40                                                  
CONECT   22   21   23   16                                                  
CONECT   23   22   24   12                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36   11                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

RDKit          3D

40 43  0  0  0  0  0  0  0  0999 V2000
    4.1783   -2.4834   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.4013   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.1746   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -0.0527    0.3648 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2633    1.0432    0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    2.2484   -0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2319    2.9487    1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3141    3.9996    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    5.1528    1.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    3.4522   -0.4600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.2680   -0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4686    1.1353   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    0.0633    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151   -1.0629    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627   -2.1010    0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2417   -0.9796    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -2.0246    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893   -3.1606    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4374   -1.9209    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588   -0.7954   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    0.2361   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7607    0.1466   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.2678   -0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    2.3214   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882   -3.3639   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -2.8648   -1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -2.1337   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -1.6630    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.4566   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.1041   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -0.8463   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -0.4182    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    2.9318   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    3.4489    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3154    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    2.3347   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -3.9425    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824   -2.7632    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.7306   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.1293   -1.2831 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
 11 36  1  6
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Frenolicin	MeSH

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(11R,15R,17R)-4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

Traditional Name

(11R,15R,17R)-4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,15}]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

CAS Registry Number

Not Available

SMILES

CCC[C@H]1O[C@@H]2CC(=O)O[C@@H]2C2=C1C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3/t10-,11-,18+/m1/s1

InChI Key

AVCPRTNVVRPELB-YRUZYCQGSA-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 fradiae	LOTUS Database	35616633
Streptomyces roseofulvus	NPAtlas	711620

Species Where Detected

Species Name	Source	Reference
Streptomyces fradiae AM-3867	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.69	ALOGPS
logP	2.42	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.21	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.39 m³·mol⁻¹	ChemAxon
Polarizability	32.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA015910

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018203

Chemspider ID

143304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163292

PDB ID

Not Available

ChEBI ID

48201

Good Scents ID

Not Available

References

General References

Wang X, Shaaban KA, Elshahawi SI, Ponomareva LV, Sunkara M, Zhang Y, Copley GC, Hower JC, Morris AJ, Kharel MK, Thorson JS: Frenolicins C-G, pyranonaphthoquinones from Streptomyces sp. RM-4-15. J Nat Prod. 2013 Aug 23;76(8):1441-7. doi: 10.1021/np400231r. Epub 2013 Aug 14. [PubMed:23944931 ]
Iwai Y, Kora A, Takahashi Y, Hayashi T, Awaya J, Masuma R, Oiwa R, Omura S: Production of deoxyfrenolicin and a new antibiotic, frenolicin B by Streptomyces roseofulvus strain AM-3867. J Antibiot (Tokyo). 1978 Oct;31(10):959-65. doi: 10.7164/antibiotics.31.959. [PubMed:711620 ]
Han C, Yu Z, Zhang Y, Wang Z, Zhao J, Huang SX, Ma Z, Wen Z, Liu C, Xiang W: Discovery of Frenolicin B as Potential Agrochemical Fungicide for Controlling Fusarium Head Blight on Wheat. J Agric Food Chem. 2021 Feb 24;69(7):2108-2117. doi: 10.1021/acs.jafc.0c04277. Epub 2021 Feb 15. [PubMed:33586974 ]
Kossor DC, Han S, Kemp FW, Slauter RW, Serota D, Rajaskarian D, Milner N, Davidovich A, Bogden JD: Administration of the oral antibiotic frenolicin-B selectively alters copper nutriture in male rats. J Nutr. 2001 Dec;131(12):3247-50. doi: 10.1093/jn/131.12.3247. [PubMed:11739875 ]
Najera C, Foubelo F, Sansano JM, Yus M: Stereodivergent routes in organic synthesis: marine natural products, lactones, other natural products, heterocycles and unnatural compounds. Org Biomol Chem. 2020 Feb 19;18(7):1279-1336. doi: 10.1039/c9ob02597a. [PubMed:32025682 ]
Ye Q, Zhang Y, Cao Y, Wang X, Guo Y, Chen J, Horn J, Ponomareva LV, Chaiswing L, Shaaban KA, Wei Q, Anderson BD, St Clair DK, Zhu H, Leggas M, Thorson JS, She QB: Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects. Cell Chem Biol. 2019 Mar 21;26(3):366-377.e12. doi: 10.1016/j.chembiol.2018.11.013. Epub 2019 Jan 17. [PubMed:30661989 ]
Zhang Y, Wang X, Sunkara M, Ye Q, Ponomereva LV, She QB, Morris AJ, Thorson JS: A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis. Org Lett. 2013 Nov 1;15(21):5566-9. doi: 10.1021/ol4027649. Epub 2013 Oct 23. [PubMed:24151973 ]
Fernandes RA, Chavan VP, Mulay SV, Manchoju A: A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin. J Org Chem. 2012 Nov 16;77(22):10455-60. doi: 10.1021/jo3019939. Epub 2012 Oct 31. [PubMed:23088749 ]
Fitzgerald JT, Henrich PP, O'Brien C, Krause M, Ekland EH, Mattheis C, Sa JM, Fidock D, Khosla C: In vitro and in vivo activity of frenolicin B against Plasmodium falciparum and P berghei. J Antibiot (Tokyo). 2011 Dec;64(12):799-801. doi: 10.1038/ja.2011.94. Epub 2011 Oct 19. [PubMed:22008701 ]
Fitzgerald JT, Ridley CP, Khosla C: Engineered biosynthesis of the antiparasitic agent frenolicin B and rationally designed analogs in a heterologous host. J Antibiot (Tokyo). 2011 Dec;64(12):759-62. doi: 10.1038/ja.2011.86. Epub 2011 Sep 21. [PubMed:21934692 ]
Eid CN, Shim J, Bikker J, Lin M: Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin. J Org Chem. 2009 Jan 2;74(1):423-6. doi: 10.1021/jo801945n. [PubMed:19053617 ]

Showing NP-Card for Frenolicin B (NP0022029)

MOL for NP0022029 (Frenolicin B)

3D MOL for NP0022029 (Frenolicin B)

3D SDF for NP0022029 (Frenolicin B)

3D-SDF for NP0022029 (Frenolicin B)

PDB for NP0022029 (Frenolicin B)

3D PDB for NP0022029 (Frenolicin B)

SMILES for NP0022029 (Frenolicin B)

INCHI for NP0022029 (Frenolicin B)

Structure for NP0022029 (Frenolicin B)

3D Structure for NP0022029 (Frenolicin B)