NP-MRD: Showing NP-Card for physodic acid (NP0299310)

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Record Information

Version

2.0

Created at

2022-09-10 11:04:13 UTC

Updated at

2022-09-10 11:04:13 UTC

NP-MRD ID

NP0299310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

physodic acid

Description

Physodic acid, also known as physodate, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). physodic acid is found in Flavoparmelia springtonensis, Hypogymnia enteromorpha, Hypotrachyna livida and Rhizoplaca melanophthalma. Physodic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161515212D          

 34 36  0  0  0  0            999 V2000
    4.1168   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9746   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6891   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6891   -0.3569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4036   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325    0.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325    0.8806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5470   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5470   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3150   -1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5581   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3808   -2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8456   -1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6683   -1.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1330   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9557   -1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4204   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7388   -3.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5615   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9194   -3.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0262   -2.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740   -3.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6320   -4.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4514   -3.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0934   -2.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2707   -3.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096   -2.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -2.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  9 34  1  0  0  0  0
 14 34  2  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    9.4997    1.2299    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216    0.6101    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6087    0.1774   -1.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423   -0.4508   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1900    0.4651   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962   -0.2585   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -0.7444   -1.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816   -0.3586    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8938   -1.0263    0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.3375    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -2.9833    1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827   -4.2836    1.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -2.3642    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072   -1.0749    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358   -0.4307    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0026    0.9111   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    1.4536    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.6080   -1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    1.6114   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    2.7360   -1.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849    2.9636   -1.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    4.1344   -2.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    1.9580   -1.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3872    2.0889   -1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2148    1.2233   -1.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9593    3.2124   -2.0287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4453    0.7924   -0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028   -0.2802   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895   -0.0080    1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6727   -1.0942    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9212   -1.2995    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7689   -2.4173    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0550    0.6425   -0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359   -0.5882   -0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2616    0.5607    0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4970    2.1759    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7284    1.5161   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1193   -0.2025    0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3959    1.3919    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5530    1.0054   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817   -0.6297   -1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -1.3863   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -0.7455   -2.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0420    1.3529   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722    0.8471    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -1.1729    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    0.3852    1.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -2.8541    1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815   -4.4157    2.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -2.8780    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576    3.5198   -1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3884    4.4839   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840    3.0669   -2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -1.1921   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0749   -0.6534   -0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827   -0.0196    1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1705    1.0100    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802   -2.0318    1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0334   -0.8951    2.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6857   -1.6322   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4912   -0.3597    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5466   -2.7546    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2343   -2.0186    2.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1099   -3.2863    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 23 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 27 33  2  0
 33 34  1  0
 15  9  1  0
 33 19  1  0
 34 14  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  8 46  1  0
  8 47  1  0
 10 48  1  0
 12 49  1  0
 13 50  1  0
 20 51  1  0
 22 52  1  0
 26 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
 30 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
M  END


  Mrv1533004161515212D          

 34 36  0  0  0  0            999 V2000
    4.1168   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9746   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6891   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6891   -0.3569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4036   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325    0.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325    0.8806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5470   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5470   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3150   -1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5581   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3808   -2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8456   -1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6683   -1.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1330   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9557   -1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4204   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7388   -3.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5615   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9194   -3.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0262   -2.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2740   -3.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6320   -4.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4514   -3.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0934   -2.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2707   -3.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7096   -2.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -2.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8325   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  9 34  1  0  0  0  0
 14 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)CC1=CC(O)=CC2=C1C(=O)OC1=CC(O)=C(C(O)=O)C(CCCCC)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O8/c1-3-5-7-9-16(27)11-15-12-17(28)13-20-22(15)26(32)34-21-14-19(29)23(25(30)31)18(24(21)33-20)10-8-6-4-2/h12-14,28-29H,3-11H2,1-2H3,(H,30,31)

> <INCHI_KEY>
KVTYWHGIZSCFLG-UHFFFAOYSA-N

> <FORMULA>
C26H30O8

> <MOLECULAR_WEIGHT>
470.518

> <EXACT_MASS>
470.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.91939881487682

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,14-dihydroxy-10-oxo-12-(2-oxoheptyl)-4-pentyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-5-carboxylic acid

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
6.955486563666668

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.029724336160118

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.566754473277582

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7834209002278354

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
125.99549999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,14-dihydroxy-10-oxo-12-(2-oxoheptyl)-4-pentyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.685  -2.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.018  -2.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.352  -2.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.686  -2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.019  -2.976   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.353  -2.206   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.353  -0.666   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.687  -2.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.020  -2.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.020  -0.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.354   0.104   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.354   1.644   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.688  -0.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.688  -2.206   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.121  -2.769   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      21.575  -4.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.111  -4.355   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.978  -3.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.514  -3.198   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.382  -1.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.917  -2.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.785  -0.768   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.779  -5.743   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.315  -5.858   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      25.983  -7.246   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      26.182  -4.586   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      22.912  -7.015   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      23.580  -8.403   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      21.376  -6.900   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.708  -5.513   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      19.172  -5.628   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.125  -4.499   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.653  -4.953   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.354  -2.976   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   16   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    9   14                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Physodate	Generator
Physodalic acid	MeSH
6,14-Dihydroxy-10-oxo-12-(2-oxoheptyl)-4-pentyl-2,9-dioxatricyclo[9.4.0.0,]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylate	Generator

Chemical Formula

C₂₆H₃₀O₈

Average Mass

470.5180 Da

Monoisotopic Mass

470.19407 Da

IUPAC Name

6,14-dihydroxy-10-oxo-12-(2-oxoheptyl)-4-pentyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-5-carboxylic acid

Traditional Name

6,14-dihydroxy-10-oxo-12-(2-oxoheptyl)-4-pentyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)CC1=CC(O)=CC2=C1C(=O)OC1=CC(O)=C(C(O)=O)C(CCCCC)=C1O2

InChI Identifier

InChI=1S/C26H30O8/c1-3-5-7-9-16(27)11-15-12-17(28)13-20-22(15)26(32)34-21-14-19(29)23(25(30)31)18(24(21)33-20)10-8-6-4-2/h12-14,28-29H,3-11H2,1-2H3,(H,30,31)

InChI Key

KVTYWHGIZSCFLG-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
Flavoparmelia springtonensis	LOTUS Database	35616633
Hypogymnia enteromorpha	LOTUS Database	35616633
Hypotrachyna livida	LOTUS Database	35616633
Rhizoplaca melanophthalma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Diaryl ether
Salicylic acid or derivatives
Hydroxybenzoic acid
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Dioxepine
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	5.36	ALOGPS
logP	6.96	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	2.57	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126 m³·mol⁻¹	ChemAxon
Polarizability	49.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65751

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for physodic acid (NP0299310)

MOL for NP0299310 (physodic acid)

3D MOL for NP0299310 (physodic acid)

3D SDF for NP0299310 (physodic acid)

3D-SDF for NP0299310 (physodic acid)

PDB for NP0299310 (physodic acid)

3D PDB for NP0299310 (physodic acid)

SMILES for NP0299310 (physodic acid)

INCHI for NP0299310 (physodic acid)

Structure for NP0299310 (physodic acid)

3D Structure for NP0299310 (physodic acid)