NP-MRD: Showing NP-Card for flavaspidic acid bb (NP0189535)

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Record Information

Version

2.0

Created at

2022-09-04 06:01:56 UTC

Updated at

2022-09-04 06:01:56 UTC

NP-MRD ID

NP0189535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

flavaspidic acid bb

Description

Flavaspidic acid, also known as flavaspidate, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. flavaspidic acid bb is found in Dryopteris aitoniana. flavaspidic acid bb was first documented in 2010 (PMID: 19898869). Based on a literature review a small amount of articles have been published on Flavaspidic acid (PMID: 35956948) (PMID: 35840879) (PMID: 33383880) (PMID: 23178515).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208012D          

 32 33  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -4.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
   -6.9882    2.2394   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7772    0.8200    0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7002    0.7848    1.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4104    1.2525    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    2.5038    0.8910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374    0.3517    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875    0.9044   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262    2.2578   -0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348    0.0990   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.7449   -1.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250    0.5756   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885    0.9343    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1829    1.4646    1.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257    0.7574    1.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    1.1612    2.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371    0.2092    0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482    0.0398    1.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5570   -0.1692   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356   -0.7086   -1.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6383   -1.0099   -2.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562   -0.9422   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823    0.3306   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2739    0.1983   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    0.0262   -1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4311   -0.3618   -2.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466   -1.1854   -1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.8771   -1.7733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -1.9347   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771   -2.6749   -1.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -2.9741    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6322   -1.0524   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7589   -1.5792    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6765    2.1603   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4088    2.9204    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0285    2.6035   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7483    0.4652    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5051    0.2303   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0075    1.4440    2.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6148   -0.2091    1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.8240   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727    1.8115   -1.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1761    0.2468   -2.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.7404    2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0823    0.3761    3.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    2.1084    3.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4392    1.4949    3.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434    0.2744    2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0382   -1.2526    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5954   -1.7219   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734    1.1436   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8779    0.5957   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9694   -0.2650   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2423   -0.3497    0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6371    1.2327    0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930   -0.3469   -3.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -2.6002   -1.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143   -2.9598   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -1.9328   -2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939   -3.5762   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0545   -3.2439    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024   -3.8465   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -2.5537    1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 24  2  0
 24 25  1  0
 24 11  1  0
 11 10  1  0
 10  9  1  0
  9 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 31 32  2  0
 31  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  6  7  2  0
  7  8  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
  7  9  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 22 50  1  0
 22 51  1  0
 21 48  1  0
 21 49  1  0
 25 55  1  0
 10 41  1  0
 10 42  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
  3 38  1  0
  3 39  1  0
  2 36  1  0
  2 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  8 40  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
M  END


  Mrv1652309042208012D          

 32 33  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -4.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 24  2  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=C(O)C(CC2=C(O)C(C)(C)C(=O)C(C(=O)CCC)=C2O)=C(O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-6-8-14(25)16-19(28)11(3)18(27)12(20(16)29)10-13-21(30)17(15(26)9-7-2)23(32)24(4,5)22(13)31/h27-31H,6-10H2,1-5H3

> <INCHI_KEY>
NHVQLOCTXSMKIX-UHFFFAOYSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.709769750636816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

> <JCHEM_LOGP>
5.370587367333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.4001539863307695

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7977404452006134

> <JCHEM_PKA_STRONGEST_BASIC>
-4.59211873740511

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
121.76329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.136  -7.861   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.324  -1.130   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.344  -1.130   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   18   11   25                                                  
CONECT   25   24                                                            
CONECT   26    9   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28    6   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
Flavaspidate	Generator

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4960 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

Traditional Name

2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=C(O)C(CC2=C(O)C(C)(C)C(=O)C(C(=O)CCC)=C2O)=C(O)C(C)=C1O

InChI Identifier

InChI=1S/C24H30O8/c1-6-8-14(25)16-19(28)11(3)18(27)12(20(16)29)10-13-21(30)17(15(26)9-7-2)23(32)24(4,5)22(13)31/h27-31H,6-10H2,1-5H3

InChI Key

NHVQLOCTXSMKIX-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Dryopteris aitoniana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phloroglucinol derivative
P-cresol
O-cresol
Benzoyl
Aryl alkyl ketone
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Cyclic ketone
Polyol
Enol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	5.37	ChemAxon
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.76 m³·mol⁻¹	ChemAxon
Polarizability	46.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00050591

Chemspider ID

7942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flavaspidic acid

METLIN ID

Not Available

PubChem Compound

8237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Y, Liu B, Wang X, Fan Y: Comparison of Constituents and Antioxidant Activity of Above-Ground and Underground Parts of Dryopteris crassirhizoma Nakai Based on HS-SPME-GC-MS and UPLC/Q-TOF-MS. Molecules. 2022 Aug 5;27(15):4991. doi: 10.3390/molecules27154991. [PubMed:35956948 ]
Cai Z, Mo Z, Zheng S, Lan S, Xie S, Lu J, Tang C, Shen Z: Flavaspidic acid BB combined with mupirocin improves its anti-bacterial and anti-biofilm activities against Staphylococcus epidermidis. BMC Microbiol. 2022 Jul 15;22(1):179. doi: 10.1186/s12866-022-02578-y. [PubMed:35840879 ]
Yuk HJ, Kim JY, Sung YY, Kim DS: Phloroglucinol Derivatives from Dryopteris crassirhizoma as Potent Xanthine Oxidase Inhibitors. Molecules. 2020 Dec 29;26(1):122. doi: 10.3390/molecules26010122. [PubMed:33383880 ]
Yang Q, Gao L, Si J, Sun Y, Liu J, Cao L, Feng WH: Inhibition of porcine reproductive and respiratory syndrome virus replication by flavaspidic acid AB. Antiviral Res. 2013 Jan;97(1):66-73. doi: 10.1016/j.antiviral.2012.11.004. Epub 2012 Nov 21. [PubMed:23178515 ]
Magalhaes LG, Kapadia GJ, da Silva Tonuci LR, Caixeta SC, Parreira NA, Rodrigues V, Da Silva Filho AA: In vitro schistosomicidal effects of some phloroglucinol derivatives from Dryopteris species against Schistosoma mansoni adult worms. Parasitol Res. 2010 Jan;106(2):395-401. doi: 10.1007/s00436-009-1674-8. Epub 2009 Nov 7. [PubMed:19898869 ]
LOTUS database [Link]

Showing NP-Card for flavaspidic acid bb (NP0189535)

MOL for NP0189535 (flavaspidic acid bb)

3D MOL for NP0189535 (flavaspidic acid bb)

3D SDF for NP0189535 (flavaspidic acid bb)

3D-SDF for NP0189535 (flavaspidic acid bb)

PDB for NP0189535 (flavaspidic acid bb)

3D PDB for NP0189535 (flavaspidic acid bb)

SMILES for NP0189535 (flavaspidic acid bb)

INCHI for NP0189535 (flavaspidic acid bb)

Structure for NP0189535 (flavaspidic acid bb)

3D Structure for NP0189535 (flavaspidic acid bb)