NP-MRD: Showing NP-Card for Psoromic acid (NP0004827)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:14:18 UTC

Updated at

2021-07-15 16:50:16 UTC

NP-MRD ID

NP0004827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psoromic acid

Provided By

NPAtlas

Description

Psoromic acid is found in Givotia madagascariensis, Lepraria eburnea, Rhizoplaca melanophthalma and Unknown-fungus sp.. Psoromic acid was first documented in 1963 (PMID: 14040789). Based on a literature review very few articles have been published on 15-formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]Pentadeca-1(11),3(8),4,6,12,14-hexaene-4-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 40 42  0  0  0  0            999 V2000
    5.6930    0.6640   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    1.2369    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    0.7042   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.3755   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -0.8869   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1142   -1.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3547   -2.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -3.0523   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.3069   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649    0.7880    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374    1.2716    0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    2.4529    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536    1.5301    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.0124    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.1578    2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    0.2285    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    0.5032    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    1.3936    2.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.1230    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714   -0.9667   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.5264   -1.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -1.2090   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -2.0325   -2.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613   -2.6107   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.5908   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -0.9530   -0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    1.4433   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.4288   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.2455   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799   -0.8567   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529   -3.6089   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    3.2647    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    2.8238    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    2.1596    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.9433    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3088    2.4346    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    1.6104    2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    0.0452    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -2.1269   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1564   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  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
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 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  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 11  3  1  0  0  0  0
 25 16  1  0  0  0  0
 26  9  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  8 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 19 38  1  0  0  0  0
 21 39  1  0  0  0  0
 23 40  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    5.6930    0.6640   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    1.2369    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    0.7042   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.3755   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -0.8869   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1142   -1.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3547   -2.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -3.0523   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.3069   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649    0.7880    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374    1.2716    0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    2.4529    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536    1.5301    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.0124    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.1578    2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    0.2285    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    0.5032    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    1.3936    2.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.1230    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714   -0.9667   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.5264   -1.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -1.2090   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -2.0325   -2.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613   -2.6107   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.5908   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -0.9530   -0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    1.4433   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.4288   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.2455   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799   -0.8567   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529   -3.6089   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    3.2647    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    2.8238    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    2.1596    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.9433    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3088    2.4346    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    1.6104    2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    0.0452    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -2.1269   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1564   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 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  1  0
 23 24  2  0
 22 25  2  0
 25 26  1  0
 11  3  1  0
 25 16  1  0
 26  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 23 40  1  0
M  END


  Mrv1652306242121113D          

 40 42  0  0  0  0            999 V2000
    5.6930    0.6640   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    1.2369    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    0.7042   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.3755   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -0.8869   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1142   -1.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3547   -2.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -3.0523   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.3069   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649    0.7880    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374    1.2716    0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    2.4529    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536    1.5301    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.0124    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.1578    2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    0.2285    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    0.5032    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    1.3936    2.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.1230    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714   -0.9667   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.5264   -1.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -1.2090   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -2.0325   -2.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613   -2.6107   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.5908   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -0.9530   -0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    1.4433   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.4288   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.2455   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799   -0.8567   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529   -3.6089   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    3.2647    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    2.8238    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    2.1596    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.9433    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3088    2.4346    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    1.6104    2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    0.0452    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -2.1269   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1564   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  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
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 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  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 11  3  1  0  0  0  0
 25 16  1  0  0  0  0
 26  9  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  8 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 19 38  1  0  0  0  0
 21 39  1  0  0  0  0
 23 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C2OC3=C(C([H])=O)C(O[H])=C([H])C(=C3C(=O)OC2=C(C(OC([H])([H])[H])=C1[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O8/c1-7-4-11(20)10(6-19)15-13(7)18(23)26-14-8(2)12(24-3)5-9(17(21)22)16(14)25-15/h4-6,20H,1-3H3,(H,21,22)

> <INCHI_KEY>
FUCWJKJZOHOLEO-UHFFFAOYSA-N

> <FORMULA>
C18H14O8

> <MOLECULAR_WEIGHT>
358.299

> <EXACT_MASS>
358.068867424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98368173756059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-4-carboxylic acid

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.5474140396666662

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.262924911239922

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3341579740269776

> <JCHEM_PKA_STRONGEST_BASIC>
-3.805731087479576

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
90.4104

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    5.6930    0.6640   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    1.2369    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    0.7042   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.3755   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -0.8869   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1142   -1.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3547   -2.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -3.0523   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.3069   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649    0.7880    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374    1.2716    0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    2.4529    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536    1.5301    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.0124    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.1578    2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    0.2285    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    0.5032    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    1.3936    2.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.1230    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714   -0.9667   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.5264   -1.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -1.2090   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -2.0325   -2.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613   -2.6107   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.5908   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -0.9530   -0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    1.4433   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.4288   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.2455   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799   -0.8567   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529   -3.6089   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    3.2647    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    2.8238    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    2.1596    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.9433    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3088    2.4346    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    1.6104    2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    0.0452    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -2.1269   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1564   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 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  1  0
 23 24  2  0
 22 25  2  0
 25 26  1  0
 11  3  1  0
 25 16  1  0
 26  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.693   0.664  -0.602  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.582   1.237   0.063  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.309   0.704  -0.116  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -0.376  -0.925  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.763  -0.887  -1.079  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.648  -2.114  -1.835  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.439  -2.355  -2.799  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.703  -3.052  -1.539  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.709  -0.307  -0.428  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.965   0.788   0.395  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.237   1.272   0.538  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.495   2.453   1.426  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.054   1.530   1.166  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.142   1.012   1.659  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.522   1.158   2.814  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.086   0.229   0.832  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.370   0.503   1.256  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.664   1.394   2.399  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.346  -0.123   0.519  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.071  -0.967  -0.572  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.144  -1.526  -1.219  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.783  -1.209  -0.957  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.451  -2.033  -2.117  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.261  -2.611  -2.863  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.763  -0.591  -0.223  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.506  -0.953  -0.733  0.00  0.00           O+0
HETATM   27  H   UNK     0       6.508   1.443  -0.574  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.452   0.429  -1.649  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.006  -0.246  -0.045  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.880  -0.857  -1.458  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.653  -3.609  -0.717  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.765   3.265   1.189  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.519   2.824   1.289  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.370   2.160   2.490  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.698   0.943   3.386  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.309   2.435   2.307  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.780   1.610   2.267  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.391   0.045   0.796  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.122  -2.127  -1.978  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.425  -2.156  -2.363  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   31                                                       
CONECT    9    5   10   26                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12    3                                                  
CONECT   12   11   32   33   34                                             
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   35   36   37                                             
CONECT   19   17   20   38                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   39                                                       
CONECT   22   20   23   25                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23                                                            
CONECT   25   22   26   16                                                  
CONECT   26   25    9                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    8                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   18                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   21                                                            
CONECT   40   23                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
    5.6930    0.6640   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    1.2369    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    0.7042   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.3755   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -0.8869   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1142   -1.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3547   -2.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -3.0523   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -0.3069   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9649    0.7880    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374    1.2716    0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    2.4529    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536    1.5301    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.0124    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.1578    2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    0.2285    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701    0.5032    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    1.3936    2.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.1230    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714   -0.9667   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1439   -1.5264   -1.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -1.2090   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507   -2.0325   -2.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2613   -2.6107   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.5908   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058   -0.9530   -0.7325 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083    1.4433   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524    0.4288   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.2455   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799   -0.8567   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529   -3.6089   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    3.2647    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5190    2.8238    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    2.1596    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.9433    3.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3088    2.4346    2.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    1.6104    2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    0.0452    0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -2.1269   -1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1564   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 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  1  0
 23 24  2  0
 22 25  2  0
 25 26  1  0
 11  3  1  0
 25 16  1  0
 26  9  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 23 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
15-Formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0,]pentadeca-1(11),3(8),4,6,12,14-hexaene-4-carboxylate	Generator
4-Formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo(b,e)(1,4)dioxepine-6-carboxylic acid	MeSH
Psoromate	Generator
15-Formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaene-4-carboxylate	Generator

Chemical Formula

C₁₈H₁₄O₈

Average Mass

358.2990 Da

Monoisotopic Mass

358.06887 Da

IUPAC Name

15-formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-4-carboxylic acid

Traditional Name

15-formyl-14-hydroxy-6-methoxy-7,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C2=C(OC3=C(C(C)=CC(O)=C3C=O)C(=O)O2)C(=C1)C(O)=O

InChI Identifier

InChI=1S/C18H14O8/c1-7-4-11(20)10(6-19)15-13(7)18(23)26-14-8(2)12(24-3)5-9(17(21)22)16(14)25-15/h4-6,20H,1-3H3,(H,21,22)

InChI Key

FUCWJKJZOHOLEO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Givotia madagascariensis	LOTUS Database	35616633
Lepraria eburnea	LOTUS Database	35616633
Rhizoplaca melanophthalma	LOTUS Database	35616633
Unknown-fungus sp.	NPAtlas	14040789

Chemical Taxonomy

Description

This compound 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
M-methoxybenzoic acid or derivatives
Anisole
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Alkyl aryl ether
Aryl-aldehyde
Dioxepine
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aldehyde
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	2.29	ALOGPS
logP	3.55	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.41 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017497

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

ARATANI H, NAKAGAWA A, TANIGUCHI T, TANAKA M: [Pharmacological studies on psoromic acid, a constituent of lichens]. J Antibiot B. 1963 Feb;16:4-7. [PubMed:14040789 ]

Showing NP-Card for Psoromic acid (NP0004827)

MOL for NP0004827 (Psoromic acid)

3D MOL for NP0004827 (Psoromic acid)

3D SDF for NP0004827 (Psoromic acid)

3D-SDF for NP0004827 (Psoromic acid)

PDB for NP0004827 (Psoromic acid)

3D PDB for NP0004827 (Psoromic acid)

SMILES for NP0004827 (Psoromic acid)

INCHI for NP0004827 (Psoromic acid)

Structure for NP0004827 (Psoromic acid)

3D Structure for NP0004827 (Psoromic acid)