NP-MRD: Showing NP-Card for Paneolilludinic acid (NP0005691)

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Record Information

Version

2.0

Created at

2020-12-09 02:52:22 UTC

Updated at

2021-07-15 16:52:43 UTC

NP-MRD ID

NP0005691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paneolilludinic acid

Provided By

NPAtlas

Description

Paneolilludinic acid, also known as paneolilludinate, belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. Paneolilludinic acid is found in Panaeolus retirugis. Paneolilludinic acid was first documented in 2004 (PMID: 15712666). Based on a literature review very few articles have been published on Paneolilludinic acid (PMID: 33963522).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118223D          

 40 42  0  0  0  0            999 V2000
   -0.4894   -2.5089   -0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1421   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.5447    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.9417    0.2787 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6066    0.3730   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0099    0.3602    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.5938   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    1.6188   -2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.2880   -2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.4502    0.5775 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4097    0.8117    0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7097    1.5591    0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9811    0.8121    0.5618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1460    1.6745    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.6426    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.5048   -0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418   -0.6930   -1.2283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0796   -1.4792    0.0335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3300   -3.2029    0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439   -2.8147   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832   -2.5334   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.6932   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.2397    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.6338    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.1090    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    0.5484   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876   -0.5906   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.6855    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.3506   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7858    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334    1.3961   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    2.6257    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    2.5656    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    1.0728    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    2.0293   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.3200    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -1.2083   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.0873   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -1.2532    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807   -2.5602   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16  2  1  6  0  0  0
 11  3  1  0  0  0  0
 18 16  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  1  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.4894   -2.5089   -0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1421   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.5447    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.9417    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.3730   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0099    0.3602    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.5938   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    1.6188   -2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.2880   -2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.4502    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097    0.8117    0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7097    1.5591    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.8121    0.5618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1460    1.6745    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.6426    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.5048   -0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418   -0.6930   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -1.4792    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300   -3.2029    0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439   -2.8147   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832   -2.5334   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.6932   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.2397    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.6338    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.1090    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    0.5484   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876   -0.5906   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.6855    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.3506   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7858    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334    1.3961   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    2.6257    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    2.5656    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    1.0728    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    2.0293   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.3200    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -1.2083   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.0873   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -1.2532    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807   -2.5602   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16  2  1  6
 11  3  1  0
 18 16  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv1652306242118223D          

 40 42  0  0  0  0            999 V2000
   -0.4894   -2.5089   -0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1421   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.5447    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.9417    0.2787 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6066    0.3730   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0099    0.3602    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.5938   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    1.6188   -2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.2880   -2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.4502    0.5775 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4097    0.8117    0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7097    1.5591    0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9811    0.8121    0.5618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1460    1.6745    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.6426    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.5048   -0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418   -0.6930   -1.2283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0796   -1.4792    0.0335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3300   -3.2029    0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439   -2.8147   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832   -2.5334   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.6932   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.2397    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.6338    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.1090    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    0.5484   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876   -0.5906   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.6855    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.3506   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7858    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334    1.3961   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    2.6257    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    2.5656    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    1.0728    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    2.0293   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.3200    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -1.2083   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.0873   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -1.2532    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807   -2.5602   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16  2  1  6  0  0  0
 11  3  1  0  0  0  0
 18 16  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  1  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C2=C(C([H])([H])[H])C3(C([H])([H])C3([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])[C@]2([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-11-8-13(2,12(16)17)6-10(11)7-14(3,18)15(9)4-5-15/h10,18H,4-8H2,1-3H3,(H,16,17)/t10-,13-,14-/m0/s1

> <INCHI_KEY>
KPHPOAIUDVWBRH-BPNCWPANSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.010180458596924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2'S,6'S,7'aS)-6'-hydroxy-2',4',6'-trimethyl-1',2',3',6',7',7'a-hexahydrospiro[cyclopropane-1,5'-indene]-2'-carboxylic acid

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.011939465666666

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615241753032982

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48949664432487794

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
68.75009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2'S,6'S,7'aS)-6'-hydroxy-2',4',6'-trimethyl-1',3',7',7'a-tetrahydrospiro[cyclopropane-1,5'-indene]-2'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.4894   -2.5089   -0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1421   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.5447    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.9417    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.3730   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0099    0.3602    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.5938   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    1.6188   -2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.2880   -2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.4502    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097    0.8117    0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7097    1.5591    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.8121    0.5618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1460    1.6745    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.6426    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.5048   -0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418   -0.6930   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -1.4792    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300   -3.2029    0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439   -2.8147   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832   -2.5334   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.6932   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.2397    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.6338    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.1090    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    0.5484   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876   -0.5906   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.6855    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.3506   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7858    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334    1.3961   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    2.6257    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    2.5656    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    1.0728    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    2.0293   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.3200    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -1.2083   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.0873   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -1.2532    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807   -2.5602   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16  2  1  6
 11  3  1  0
 18 16  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 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      -0.489  -2.509  -0.768  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.621  -1.142  -0.206  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.464  -0.545   0.220  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.908  -0.942   0.279  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.607   0.373  -0.066  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.010   0.360   0.470  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.616   0.594  -1.540  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.058   1.619  -2.049  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.220  -0.288  -2.412  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.760   1.450   0.578  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.410   0.812   0.793  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.710   1.559   0.134  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.981   0.812   0.562  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.146   1.675   0.145  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.914   0.643   1.926  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.945  -0.505  -0.143  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.942  -0.693  -1.228  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.080  -1.479   0.034  0.00  0.00           C+0
HETATM   19  H   UNK     0      -0.330  -3.203   0.096  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.344  -2.815  -1.390  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.483  -2.533  -1.336  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.172  -1.693  -0.476  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.164  -1.240   1.303  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.270  -0.634   0.906  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.112   1.109   1.264  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.757   0.548  -0.342  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.188  -0.591  -2.247  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.233   1.686   1.563  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.730   2.351  -0.038  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.190   0.786   1.888  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.633   1.396  -0.964  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.764   2.626   0.409  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.246   2.566   0.798  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.079   1.073   0.349  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.078   2.029  -0.882  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.966  -0.320   2.175  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.635  -1.208  -2.167  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.690   0.087  -1.391  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.880  -1.253   0.764  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.881  -2.560  -0.073  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   16                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   22   23                                             
CONECT    5    4    6    7   10                                             
CONECT    6    5   24   25   26                                             
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   27                                                       
CONECT   10    5   11   28   29                                             
CONECT   11   10   12    3   30                                             
CONECT   12   11   13   31   32                                             
CONECT   13   12   14   15   16                                             
CONECT   14   13   33   34   35                                             
CONECT   15   13   36                                                       
CONECT   16   13   17    2   18                                             
CONECT   17   16   18   37   38                                             
CONECT   18   17   16   39   40                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    6                                                            
CONECT   25    6                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
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
   -0.4894   -2.5089   -0.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1421   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.5447    0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.9417    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.3730   -0.0659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0099    0.3602    0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.5938   -1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    1.6188   -2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.2880   -2.4124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    1.4502    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097    0.8117    0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7097    1.5591    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.8121    0.5618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1460    1.6745    0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.6426    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.5048   -0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418   -0.6930   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -1.4792    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300   -3.2029    0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3439   -2.8147   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832   -2.5334   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.6932   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -1.2397    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.6338    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    1.1090    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    0.5484   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876   -0.5906   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    1.6855    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    2.3506   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7858    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334    1.3961   -0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    2.6257    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2456    2.5656    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    1.0728    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775    2.0293   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.3200    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -1.2083   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896    0.0873   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -1.2532    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807   -2.5602   -0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16  2  1  6
 11  3  1  0
 18 16  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Paneolilludinate	Generator
(2's,6's,7'AS)-6'-hydroxy-2',4',6'-trimethyl-1',2',3',6',7',7'a-hexahydrospiro[cyclopropane-1,5'-indene]-2'-carboxylate	Generator

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

(2'S,6'S,7'aS)-6'-hydroxy-2',4',6'-trimethyl-1',2',3',6',7',7'a-hexahydrospiro[cyclopropane-1,5'-indene]-2'-carboxylic acid

Traditional Name

(2'S,6'S,7'aS)-6'-hydroxy-2',4',6'-trimethyl-1',3',7',7'a-tetrahydrospiro[cyclopropane-1,5'-indene]-2'-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C2C[C@](C)(C[C@H]2C[C@](C)(O)C11CC1)C(O)=O

InChI Identifier

InChI=1S/C15H22O3/c1-9-11-8-13(2,12(16)17)6-10(11)7-14(3,18)15(9)4-5-15/h10,18H,4-8H2,1-3H3,(H,16,17)/t10-,13-,14-/m0/s1

InChI Key

KPHPOAIUDVWBRH-BPNCWPANSA-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
Panaeolus retirugis	NPAtlas	15712666

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Illudanes and illudins

Alternative Parents

Substituents

Illudine sesquiterpenoid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.92	ALOGPS
logP	2.01	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.75 m³·mol⁻¹	ChemAxon
Polarizability	28.01 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

NPA014863

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9656914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11482094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma W, Huang Y, Lin L, Zhu X, Chen Y, Xu H, Wei X: Two new biologically active illudane sesquiterpenes from the mycelial cultures of Panaeolus retirugis. J Antibiot (Tokyo). 2004 Nov;57(11):721-5. doi: 10.7164/antibiotics.57.721. [PubMed:15712666 ]
Zhai YJ, Li JN, Gao YQ, Gao LL, Wang DC, Han WB, Gao JM: Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae. Nat Prod Bioprospect. 2021 Jun;11(3):325-332. doi: 10.1007/s13659-021-00299-9. Epub 2021 May 7. [PubMed:33963522 ]

Showing NP-Card for Paneolilludinic acid (NP0005691)

MOL for NP0005691 (Paneolilludinic acid)

3D MOL for NP0005691 (Paneolilludinic acid)

3D SDF for NP0005691 (Paneolilludinic acid)

3D-SDF for NP0005691 (Paneolilludinic acid)

PDB for NP0005691 (Paneolilludinic acid)

3D PDB for NP0005691 (Paneolilludinic acid)

SMILES for NP0005691 (Paneolilludinic acid)

INCHI for NP0005691 (Paneolilludinic acid)

Structure for NP0005691 (Paneolilludinic acid)

3D Structure for NP0005691 (Paneolilludinic acid)