NP-MRD: Showing NP-Card for Fusidienol A (NP0003907)

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Record Information

Version

1.0

Created at

2020-12-09 01:27:22 UTC

Updated at

2021-07-15 16:47:42 UTC

NP-MRD ID

NP0003907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fusidienol A

Provided By

NPAtlas

Description

Fusidienol A is found in Phoma sp. It was first documented in 1997 (PMID: 11671871). Based on a literature review very few articles have been published on methyl 7-hydroxy-9-methyl-6-oxo-6H-oxepino[2,3-b]chromene-5-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 34 36  0  0  0  0            999 V2000
   -4.8715   -2.0365    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -0.8005    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7009   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -1.7555   -0.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738    0.5603    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.5903    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    3.0011    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    3.6659    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    3.0976   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8498   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    1.8242   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.6909   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    0.6339   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.4873   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.5097   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765   -1.6216    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -1.6413    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.7805    0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.4736    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.4210    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -1.4155    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    0.7452   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -2.8540    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.0602   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.1560    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    1.3116    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    3.5694    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    4.6971    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    1.5192   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -1.3598   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    0.4533   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5198    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -2.5570    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -3.0593    0.8742 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22  5  1  0  0  0  0
 22 10  2  0  0  0  0
 19 12  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
 13 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 16 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.8715   -2.0365    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -0.8005    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7009   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -1.7555   -0.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738    0.5603    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.5903    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    3.0011    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    3.6659    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    3.0976   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8498   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    1.8242   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.6909   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    0.6339   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.4873   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.5097   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765   -1.6216    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -1.6413    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.7805    0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.4736    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.4210    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -1.4155    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    0.7452   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -2.8540    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.0602   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.1560    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    1.3116    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    3.5694    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    4.6971    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    1.5192   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -1.3598   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    0.4533   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5198    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -2.5570    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -3.0593    0.8742 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 10  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
M  END


  Mrv1652306242117513D          

 34 36  0  0  0  0            999 V2000
   -4.8715   -2.0365    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -0.8005    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7009   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -1.7555   -0.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738    0.5603    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.5903    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    3.0011    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    3.6659    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    3.0976   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8498   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    1.8242   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.6909   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    0.6339   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.4873   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.5097   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765   -1.6216    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -1.6413    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.7805    0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.4736    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.4210    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -1.4155    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    0.7452   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -2.8540    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.0602   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.1560    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    1.3116    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    3.5694    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    4.6971    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    1.5192   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -1.3598   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    0.4533   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5198    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -2.5570    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -3.0593    0.8742 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22  5  1  0  0  0  0
 22 10  2  0  0  0  0
 19 12  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
 13 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 16 33  1  0  0  0  0
 18 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(OC3=C(C2=O)C(=C([H])C([H])=C([H])O3)C(=O)OC([H])([H])[H])=C([H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-8-6-10(17)13-11(7-8)22-16-12(14(13)18)9(15(19)20-2)4-3-5-21-16/h3-7,17H,1-2H3

> <INCHI_KEY>
SEBVTYCKKTZQMP-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.999979040465917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 7-hydroxy-9-methyl-6-oxo-6H-oxepino[2,3-b]chromene-5-carboxylate

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.0536391683333326

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.410260884872937

> <JCHEM_PKA_STRONGEST_BASIC>
-5.191913862326809

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
88.1454

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7-hydroxy-9-methyl-6-oxooxepino[2,3-b]chromene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.8715   -2.0365    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -0.8005    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7009   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -1.7555   -0.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738    0.5603    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.5903    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    3.0011    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    3.6659    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    3.0976   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8498   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    1.8242   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.6909   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    0.6339   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.4873   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.5097   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765   -1.6216    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -1.6413    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.7805    0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.4736    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.4210    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -1.4155    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    0.7452   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -2.8540    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.0602   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.1560    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    1.3116    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    3.5694    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    4.6971    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    1.5192   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -1.3598   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    0.4533   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5198    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -2.5570    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -3.0593    0.8742 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 10  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  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      -4.872  -2.037   0.022  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.214  -0.801   0.162  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.829  -0.701  -0.138  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.326  -1.756  -0.506  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.174   0.560   0.012  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.996   1.590   0.340  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.674   3.001   0.559  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.625   3.666   0.050  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.624   3.098  -0.807  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.012   1.850  -0.520  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.274   1.824  -0.645  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.916   0.691  -0.378  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.299   0.634  -0.507  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.025  -0.487  -0.253  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.507  -0.510  -0.403  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.377  -1.622   0.149  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.970  -1.641   0.304  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.378  -2.781   0.701  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.286  -0.474   0.033  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.085  -0.421   0.160  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.702  -1.416   0.535  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.750   0.745  -0.122  0.00  0.00           C+0
HETATM   23  H   UNK     0      -4.117  -2.854   0.073  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.269  -2.060  -1.031  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.705  -2.156   0.715  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.027   1.312   0.453  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.333   3.569   1.180  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.525   4.697   0.297  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.815   1.519  -0.822  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.845  -1.360  -1.028  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.839   0.453  -0.872  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.935  -0.520   0.620  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.894  -2.557   0.370  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.499  -3.059   0.874  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   30   31   32                                             
CONECT   16   14   17   33                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   34                                                       
CONECT   19   17   20   12                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5   10                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -4.8715   -2.0365    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137   -0.8005    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.7009   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -1.7555   -0.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738    0.5603    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.5903    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    3.0011    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254    3.6659    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6236    3.0976   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8498   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742    1.8242   -0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159    0.6909   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    0.6339   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -0.4873   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -0.5097   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765   -1.6216    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -1.6413    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -2.7805    0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -0.4736    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.4210    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019   -1.4155    0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    0.7452   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -2.8540    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.0602   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.1560    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    1.3116    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330    3.5694    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    4.6971    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    1.5192   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -1.3598   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    0.4533   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348   -0.5198    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -2.5570    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -3.0593    0.8742 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 10  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Value	Source
Methyl 7-hydroxy-9-methyl-6-oxo-6H-oxepino[2,3-b]chromene-5-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

methyl 7-hydroxy-9-methyl-6-oxo-6H-oxepino[2,3-b]chromene-5-carboxylate

Traditional Name

methyl 7-hydroxy-9-methyl-6-oxooxepino[2,3-b]chromene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=COC2=C1C(=O)C1=C(O2)C=C(C)C=C1O

InChI Identifier

InChI=1S/C16H12O6/c1-8-6-10(17)13-11(7-8)22-16-12(14(13)18)9(15(19)20-2)4-3-5-21-16/h3-7,17H,1-2H3

InChI Key

SEBVTYCKKTZQMP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Phoma sp.	NPAtlas	11671871

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Chromone
Coumarin
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	2.72	ALOGPS
logP	3.05	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.41	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.15 m³·mol⁻¹	ChemAxon
Polarizability	30 Å³	ChemAxon
Number of Rings	3	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

NPA019955

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8058447

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh SB, Ball RG, Zink DL, Monaghan RL, Polishook JD, Sanchez M, Pelaez F, Silverman KC, Lingham RB: Fusidienol A: A Novel Ras Farnesyl-Protein Transferase Inhibitor from Phoma sp. J Org Chem. 1997 Oct 17;62(21):7485-7488. doi: 10.1021/jo9708304. [PubMed:11671871 ]

Showing NP-Card for Fusidienol A (NP0003907)

MOL for NP0003907 (Fusidienol A)

3D MOL for NP0003907 (Fusidienol A)

3D SDF for NP0003907 (Fusidienol A)

3D-SDF for NP0003907 (Fusidienol A)

PDB for NP0003907 (Fusidienol A)

3D PDB for NP0003907 (Fusidienol A)

SMILES for NP0003907 (Fusidienol A)

INCHI for NP0003907 (Fusidienol A)

Structure for NP0003907 (Fusidienol A)

3D Structure for NP0003907 (Fusidienol A)