NP-MRD: Showing NP-Card for Gyrophoric acid (NP0139258)

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Record Information

Version

1.0

Created at

2022-06-29 19:46:22 UTC

Updated at

2022-06-29 19:46:22 UTC

NP-MRD ID

NP0139258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gyrophoric acid

Description

Gyrophoric acid, also known as gyrophate, 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). Gyrophoric acid is a depside that can be found in the lichen Cryptothecia rubrocincta and in Xanthoparmelia pokomyi. Gyrophoric acid is found in Acarospora rugulosa, Dimelaena oreina, Lecidea fuscoatra, Parmotrema sancti-angelii, Parmotrema tinctorum, Punctelia borreri, Rinodina alba, Umbilicaria esculenta, Umbilicaria proboscidea and Umbilicaria torrefacta. Gyrophoric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121520482D          

 34 36  0  0  0  0            999 V2000
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  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
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  2 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
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -6.9977   -1.3422    1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2936   -0.2911    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9306   -0.2345    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2025    0.6922    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967    0.7598    0.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810    0.0036   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -0.6734   -1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6237   -0.0194   -0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    0.7402    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284    1.5545    1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    0.7781    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1691    0.0559   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    0.1169   -0.5247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -0.7743    0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -1.6296    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7149   -0.7620    0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963    0.1587   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8275    1.1390   -1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8799    0.1760   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5183   -0.7395    0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9113   -0.7225    0.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7430   -1.6635    1.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683   -1.6714    1.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5732   -2.5985    1.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405   -0.7085   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -0.7491   -1.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -1.5281   -2.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8228    1.5978   -0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2207    1.5560   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7995    2.4788   -1.6503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9823    0.6133   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4141    0.5419   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0788    1.3236   -0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1222   -0.4162    0.4387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5505   -2.0090    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6931   -0.8691    2.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2489   -1.9869    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882   -0.9398    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868    0.9107    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0253    2.0739    1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2944    2.3788    0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8946    1.3712    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    1.8110   -1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1560    1.8276   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2944    0.6896   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4741    0.9107   -0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2806   -0.1431    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2489   -2.3802    1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -3.2711    2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044   -1.2907   -2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436   -1.7121   -2.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2594    2.3520   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7011    2.6981   -1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7838   -0.1840    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  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
 20 22  1  0
 22 23  2  0
 23 24  1  0
 12 25  1  0
 25 26  2  0
 26 27  1  0
  4 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 34  1  0
 32 33  2  0
 31  2  1  0
 26  8  1  0
 23 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 22 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
 28 52  1  0
 30 53  1  0
 34 54  1  0
M  END


  Mrv0541 04121520482D          

 34 36  0  0  0  0            999 V2000
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  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
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  2 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
M  END
> <DATABASE_ID>
NP0139258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(OC(=O)C2=C(C)C=C(OC(=O)C3=C(C)C=C(O)C=C3O)C=C2O)=CC(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O10/c1-10-4-13(25)7-16(26)20(10)23(31)34-15-6-12(3)21(18(28)9-15)24(32)33-14-5-11(2)19(22(29)30)17(27)8-14/h4-9,25-28H,1-3H3,(H,29,30)

> <INCHI_KEY>
ATQPZSQVWCPVGV-UHFFFAOYSA-N

> <FORMULA>
C24H20O10

> <MOLECULAR_WEIGHT>
468.414

> <EXACT_MASS>
468.105646844

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.63251007456268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[4-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoic acid

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
7.229702430666666

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.55597397995785

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.84070461309796

> <JCHEM_PKA_STRONGEST_BASIC>
-4.006403761890135

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
119.96719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gyrophoric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25    8   27                                                  
CONECT   27   26                                                            
CONECT   28    4   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Gyrophate	Generator
Gyrophic acid	Generator
4-(4-(2,4-Dihydroxy-6-methylbenzoyl)oxy)-2-hydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid	MeSH

Chemical Formula

C₂₄H₂₀O₁₀

Average Mass

468.4140 Da

Monoisotopic Mass

468.10565 Da

IUPAC Name

4-[4-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoic acid

Traditional Name

gyrophoric acid

CAS Registry Number

Not Available

SMILES

CC1=CC(OC(=O)C2=C(C)C=C(OC(=O)C3=C(C)C=C(O)C=C3O)C=C2O)=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C24H20O10/c1-10-4-13(25)7-16(26)20(10)23(31)34-15-6-12(3)21(18(28)9-15)24(32)33-14-5-11(2)19(22(29)30)17(27)8-14/h4-9,25-28H,1-3H3,(H,29,30)

InChI Key

ATQPZSQVWCPVGV-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
Acarospora rugulosa	LOTUS Database	35616633
Dimelaena oreina	LOTUS Database	35616633
Lecidea fuscoatra	LOTUS Database	35616633
Parmotrema sancti-angelii	LOTUS Database	35616633
Parmotrema tinctorum	LOTUS Database	35616633
Punctelia borreri	LOTUS Database	35616633
Rinodina alba	LOTUS Database	35616633
Umbilicaria esculenta	LOTUS Database	35616633
Umbilicaria proboscidea	LOTUS Database	35616633
Umbilicaria torrefacta	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

Depside backbone
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Phenol ester
Salicylic acid or derivatives
Benzoate ester
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Tricarboxylic acid or derivatives
Phenoxy compound
Resorcinol
Benzoyl
M-cresol
1-hydroxy-4-unsubstituted benzenoid
Phenol
Toluene
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.79	ALOGPS
logP	7.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.97 m³·mol⁻¹	ChemAxon
Polarizability	45.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

Gyrophoric acid

METLIN ID

Not Available

PubChem Compound

135728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gyrophoric acid (NP0139258)

MOL for NP0139258 (Gyrophoric acid)

3D MOL for NP0139258 (Gyrophoric acid)

3D SDF for NP0139258 (Gyrophoric acid)

3D-SDF for NP0139258 (Gyrophoric acid)

PDB for NP0139258 (Gyrophoric acid)

3D PDB for NP0139258 (Gyrophoric acid)

SMILES for NP0139258 (Gyrophoric acid)

INCHI for NP0139258 (Gyrophoric acid)

Structure for NP0139258 (Gyrophoric acid)

3D Structure for NP0139258 (Gyrophoric acid)