NP-MRD: Showing NP-Card for Pinastric acid (NP0023539)

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Record Information

Version

2.0

Created at

2021-01-06 08:36:36 UTC

Updated at

2021-07-15 17:42:01 UTC

NP-MRD ID

NP0023539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pinastric acid

Provided By

NPAtlas

Description

Pinastric acid is found in Chrysothrix candelaris, Flavoparmelia caperata, Parmelia and Vulpicida pinastri. Pinastric acid was first documented in 1976 (PMID: 932945). Based on a literature review very few articles have been published on methyl 2-[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-phenylacetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120423D          

 42 44  0  0  0  0            999 V2000
   -4.5727   -3.0608   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963   -1.7857   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.5071   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.4442   -0.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -0.1649   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    0.2060    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917    1.5377    0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.6289    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659    2.6500    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    0.2922    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.0153    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.4727    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.2417    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721   -0.4933    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.7670    0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844   -0.3648    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -0.9851   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.7472   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.5383   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -1.8717   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.8610    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.6000    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    1.5788    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3718    2.8139    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    3.0882   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691    2.0834   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9837   -3.0922   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -3.2875   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -3.8184   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.0457    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    0.6315    1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216   -1.2575    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276    0.1048    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3564    0.3591    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -1.5666   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1478   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -2.2473   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3621    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    1.3817    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    3.5630    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0668    4.0446   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    2.3404   -1.1069 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19  6  1  0  0  0  0
 26 21  1  0  0  0  0
 18 11  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
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
 22 38  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
 26 42  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5727   -3.0608   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963   -1.7857   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.5071   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.4442   -0.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -0.1649   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    0.2060    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917    1.5377    0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.6289    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659    2.6500    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    0.2922    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.0153    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.4727    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.2417    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721   -0.4933    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.7670    0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844   -0.3648    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -0.9851   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.7472   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.5383   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -1.8717   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.8610    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.6000    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    1.5788    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3718    2.8139    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    3.0882   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691    2.0834   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9837   -3.0922   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -3.2875   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -3.8184   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.0457    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    0.6315    1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216   -1.2575    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276    0.1048    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3564    0.3591    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -1.5666   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1478   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -2.2473   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3621    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    1.3817    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    3.5630    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0668    4.0446   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    2.3404   -1.1069 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  6  1  0
 26 21  1  0
 18 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  1  0
 26 42  1  0
M  END


  Mrv1652306242120423D          

 42 44  0  0  0  0            999 V2000
   -4.5727   -3.0608   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963   -1.7857   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.5071   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.4442   -0.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -0.1649   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    0.2060    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917    1.5377    0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.6289    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659    2.6500    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    0.2922    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.0153    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.4727    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.2417    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721   -0.4933    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.7670    0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844   -0.3648    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -0.9851   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.7472   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.5383   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -1.8717   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.8610    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.6000    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    1.5788    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3718    2.8139    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    3.0882   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691    2.0834   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9837   -3.0922   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -3.2875   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -3.8184   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.0457    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    0.6315    1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216   -1.2575    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276    0.1048    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3564    0.3591    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -1.5666   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1478   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -2.2473   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3621    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    1.3817    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    3.5630    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0668    4.0446   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    2.3404   -1.1069 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19  6  1  0  0  0  0
 26 21  1  0  0  0  0
 18 11  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
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
 22 38  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
 26 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)O\C1=C(\C(=O)OC([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O6/c1-24-14-10-8-13(9-11-14)15-17(21)18(26-20(15)23)16(19(22)25-2)12-6-4-3-5-7-12/h3-11,21H,1-2H3/b18-16+

> <INCHI_KEY>
KXQKSBAGVQMQSN-FBMGVBCBSA-N

> <FORMULA>
C20H16O6

> <MOLECULAR_WEIGHT>
352.342

> <EXACT_MASS>
352.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
37.1442658637516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-phenylacetate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
3.0698446020000003

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.009473442005588

> <JCHEM_PKA_STRONGEST_BASIC>
-4.831197969842443

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
95.35450000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2-ylidene](phenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5727   -3.0608   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963   -1.7857   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.5071   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.4442   -0.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -0.1649   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    0.2060    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917    1.5377    0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.6289    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659    2.6500    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    0.2922    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.0153    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.4727    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.2417    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721   -0.4933    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.7670    0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844   -0.3648    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -0.9851   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.7472   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.5383   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -1.8717   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.8610    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.6000    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    1.5788    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3718    2.8139    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    3.0882   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691    2.0834   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9837   -3.0922   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -3.2875   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -3.8184   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.0457    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    0.6315    1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216   -1.2575    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276    0.1048    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3564    0.3591    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -1.5666   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1478   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -2.2473   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3621    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    1.3817    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    3.5630    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0668    4.0446   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    2.3404   -1.1069 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  6  1  0
 26 21  1  0
 18 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  1  0
 26 42  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      -4.573  -3.061  -0.927  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.096  -1.786  -0.596  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.720  -1.507  -0.469  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.976  -2.444  -0.663  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.369  -0.165  -0.132  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.109   0.206   0.001  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.792   1.538   0.339  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.567   1.629   0.406  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.266   2.650   0.682  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.133   0.292   0.096  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.561  -0.015   0.063  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.396   0.473   1.079  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.753   0.242   1.105  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.372  -0.493   0.119  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.719  -0.767   0.074  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.684  -0.365   0.987  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.555  -0.985  -0.897  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.183  -0.747  -0.917  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.130  -0.538  -0.142  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.253  -1.872  -0.466  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.446   0.861   0.057  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.577   0.600   0.763  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.551   1.579   0.886  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.372   2.814   0.293  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.235   3.088  -0.421  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.269   2.083  -0.529  0.00  0.00           C+0
HETATM   27  H   UNK     0      -4.984  -3.092  -1.962  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.442  -3.288  -0.263  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.807  -3.818  -0.748  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.909   1.046   1.849  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.377   0.632   1.906  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.122  -1.258   1.517  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.528   0.105   0.398  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.356   0.359   1.754  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.028  -1.567  -1.681  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.597  -1.148  -1.740  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.595  -2.247  -1.340  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.702  -0.362   1.218  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.464   1.382   1.446  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.148   3.563   0.403  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.067   4.045  -0.893  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.389   2.340  -1.107  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   32   33   34                                             
CONECT   17   14   18   35                                                  
CONECT   18   17   11   36                                                  
CONECT   19   10   20    6                                                  
CONECT   20   19   37                                                       
CONECT   21    5   22   26                                                  
CONECT   22   21   23   38                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23   25   40                                                  
CONECT   25   24   26   41                                                  
CONECT   26   25   21   42                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   25                                                            
CONECT   42   26                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5727   -3.0608   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0963   -1.7857   -0.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -1.5071   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.4442   -0.6632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -0.1649   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    0.2060    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917    1.5377    0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671    1.6289    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659    2.6500    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    0.2922    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -0.0153    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.4727    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.2417    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721   -0.4933    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -0.7670    0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6844   -0.3648    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -0.9851   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.7472   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.5383   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -1.8717   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4460    0.8610    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5774    0.6000    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    1.5788    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3718    2.8139    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    3.0882   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2691    2.0834   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9837   -3.0922   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -3.2875   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -3.8184   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.0457    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    0.6315    1.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1216   -1.2575    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5276    0.1048    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3564    0.3591    1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -1.5666   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1478   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -2.2473   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3621    1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4636    1.3817    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    3.5630    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0668    4.0446   -0.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3888    2.3404   -1.1069 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  6  1  0
 26 21  1  0
 18 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  1  0
 26 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 2-[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-phenylacetic acid	Generator
Pinastrate	Generator
Pinastric acid, potassium salt	MeSH

Chemical Formula

C₂₀H₁₆O₆

Average Mass

352.3420 Da

Monoisotopic Mass

352.09469 Da

IUPAC Name

methyl 2-[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-phenylacetate

Traditional Name

methyl [(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2-ylidene](phenyl)acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=C(OC)C=C1)\C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H16O6/c1-24-14-10-8-13(9-11-14)15-17(21)18(26-20(15)23)16(19(22)25-2)12-6-4-3-5-7-12/h3-11,21H,1-2H3/b18-16+

InChI Key

KXQKSBAGVQMQSN-FBMGVBCBSA-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
Chrysothrix candelaris	LOTUS Database	35616633
Flavoparmelia caperata	LOTUS Database	35616633
Parmelia	NPAtlas	932945
Vulpicida pinastri	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	ALOGPS
logP	3.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.35 m³·mol⁻¹	ChemAxon
Polarizability	37.14 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

NPA004943

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20123550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54679633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Serra T, Polonia J: Isolation of pinastric acid and ergosterol from Parmelia caperata (L.) Arch. J Pharm Sci. 1976 May;65(5):737-8. doi: 10.1002/jps.2600650528. [PubMed:932945 ]

Showing NP-Card for Pinastric acid (NP0023539)

MOL for NP0023539 (Pinastric acid)

3D MOL for NP0023539 (Pinastric acid)

3D SDF for NP0023539 (Pinastric acid)

3D-SDF for NP0023539 (Pinastric acid)

PDB for NP0023539 (Pinastric acid)

3D PDB for NP0023539 (Pinastric acid)

SMILES for NP0023539 (Pinastric acid)

INCHI for NP0023539 (Pinastric acid)

Structure for NP0023539 (Pinastric acid)

3D Structure for NP0023539 (Pinastric acid)