NP-MRD: Showing NP-Card for 7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid (NP0286157)

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Record Information

Version

1.0

Created at

2022-09-09 14:36:49 UTC

Updated at

2022-09-09 14:36:50 UTC

NP-MRD ID

NP0286157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

Description

Physodalic acid, also known as physodalate, 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). 7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid is found in Flavoparmelia springtonensis and Hypogymnia enteromorphoides. Physodalic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502552D          

 30 32  0  0  0  0            999 V2000
   -0.9213   -4.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -3.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -4.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139    0.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -3.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   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
  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 15 30  2  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    2.6418    3.9294    1.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629    2.6056    1.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797    2.4710    2.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    1.5115    1.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    0.2543    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -0.7525    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6842   -2.0299    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909   -2.4409    0.4689 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7723   -2.9774   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2657   -4.3019   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4949   -4.5889   -0.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -5.3086   -1.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -2.6231   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5732   -3.5515   -0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0737   -1.3103   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -0.3959    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    0.9645    0.6222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887    1.5355    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    2.3939    1.6698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    1.2389    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    2.3353   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    3.5883    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    2.1954   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062    1.0069   -1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3149    1.0148   -2.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2591   -0.0675   -1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101   -1.3125   -1.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336   -1.5363   -2.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0612    0.0293   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031   -1.1340   -0.5362 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    4.5130    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2352    4.5102    2.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207    3.8307    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6109   -0.0602    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0539    0.3998    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6561   -1.7727    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -6.0869   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443   -3.2276   -0.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4505   -4.5819   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -3.5751   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1686    4.0363    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8280    4.3550    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    3.7302    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3491    3.0493   -0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7539    0.2993   -2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9304   -2.1626   -1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  9 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 26 29  2  0
 29 30  1  0
 16  6  1  0
 29 20  1  0
 30 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
 27 46  1  0
M  END


  Mrv1533004261502552D          

 30 32  0  0  0  0            999 V2000
   -0.9213   -4.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -3.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -4.3364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139    0.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -3.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   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
  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 15 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C(O)C(C(O)=O)=C(C)C2=C1OC(=O)C1=C(C)C=C(O)C(C=O)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O10/c1-7-4-12(23)10(5-21)17-13(7)20(27)30-18-11(6-28-9(3)22)15(24)14(19(25)26)8(2)16(18)29-17/h4-5,23-24H,6H2,1-3H3,(H,25,26)

> <INCHI_KEY>
SKXNIRUDASOCCN-UHFFFAOYSA-N

> <FORMULA>
C20H16O10

> <MOLECULAR_WEIGHT>
416.338

> <EXACT_MASS>
416.074346715

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
39.22692398504105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.725295626666666

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.262286993583599

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.550678754844703

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8107957883756725

> <JCHEM_POLAR_SURFACE_AREA>
156.65999999999997

> <JCHEM_REFRACTIVITY>
101.89549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -1.720  -7.501   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.248  -7.047   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.881  -8.095   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.095  -5.546   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.566  -5.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.909  -3.590   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.780  -2.543   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.692  -2.997   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.006   0.006   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.336   1.507   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.478  -0.448   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.594  -0.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.937   0.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.723  -1.635   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.111  -0.967   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.498  -1.635   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.627  -0.588   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.284   0.914   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.813   1.368   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.227   0.006   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.441  -2.543   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.312  -3.590   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.655  -5.092   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.881  -4.341   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.549  -5.728   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.341  -4.341   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    6   15                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Physodalate	Generator
Physodic acid	MeSH

Chemical Formula

C₂₀H₁₆O₁₀

Average Mass

416.3380 Da

Monoisotopic Mass

416.07435 Da

IUPAC Name

7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

Traditional Name

7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C(O)C(C(O)=O)=C(C)C2=C1OC(=O)C1=C(C)C=C(O)C(C=O)=C1O2

InChI Identifier

InChI=1S/C20H16O10/c1-7-4-12(23)10(5-21)17-13(7)20(27)30-18-11(6-28-9(3)22)15(24)14(19(25)26)8(2)16(18)29-17/h4-5,23-24H,6H2,1-3H3,(H,25,26)

InChI Key

SKXNIRUDASOCCN-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 enteromorphoides	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
Hydroxybenzoic acid
Salicylic acid or derivatives
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Dioxepine
Aryl-aldehyde
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
Organooxygen compound
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	2.9	ALOGPS
logP	3.73	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.9 m³·mol⁻¹	ChemAxon
Polarizability	39.23 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

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

5489369

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid (NP0286157)

MOL for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

3D MOL for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

3D SDF for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

3D-SDF for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

PDB for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

3D PDB for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

SMILES for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

INCHI for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

Structure for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)

3D Structure for NP0286157 (7-[(acetyloxy)methyl]-15-formyl-6,14-dihydroxy-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid)