NP-MRD: Showing NP-Card for Illudin S (NP0004898)

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Record Information

Version

2.0

Created at

2020-12-09 02:17:54 UTC

Updated at

2021-07-15 16:50:28 UTC

NP-MRD ID

NP0004898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Illudin S

Provided By

NPAtlas

Description

Illudin S is found in Omphalotus japonicus, Lamptreomyces japonicus, Omphalotus illudens and Omphalotus olivascens. Illudin S was first documented in 2003 (PMID: 14510611). Based on a literature review a small amount of articles have been published on (-)-illudin s (PMID: 34039990) (PMID: 33851984) (PMID: 32378541) (PMID: 32152397).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118093D          

 39 41  0  0  0  0            999 V2000
   -0.8860   -2.4814   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.0051   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.4410   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.9895    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    1.3503    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.1855   -0.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475    0.3882   -1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -0.0118    1.2000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3458    1.1216    1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.9789   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9190   -1.6743   -1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    1.7783    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.0256    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    1.1144    0.5694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0898    2.0364    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    1.1288    1.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.2719    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5545   -0.8666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2914   -1.0600    0.5508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4325   -2.7682   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.9325   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -2.9410    0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.3635    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -0.2175   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1274   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6457    1.4901   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.1458    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.9010    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.4334    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.6813    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -2.5446   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    1.7572    0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477    3.0504    0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133    2.0952   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    0.9537    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.2718   -1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9710    0.2626   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -0.6069    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.1627    0.6280 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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17  2  1  6  0  0  0
 10  3  1  0  0  0  0
 19 17  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  1  0  0  0
 11 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
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 16 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
 19 39  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.8860   -2.4814   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.0051   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.4410   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.9895    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    1.3503    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.1855   -0.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475    0.3882   -1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -0.0118    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458    1.1216    1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.9789   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9190   -1.6743   -1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    1.7783    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.0256    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    1.1144    0.5694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0898    2.0364    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    1.1288    1.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.2719    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5545   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914   -1.0600    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325   -2.7682   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.9325   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -2.9410    0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.3635    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -0.2175   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1274   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6457    1.4901   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.1458    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.9010    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.4334    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.6813    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -2.5446   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    1.7572    0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477    3.0504    0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0848    0.9537    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.2718   -1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9710    0.2626   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -0.6069    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.1627    0.6280 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  2  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  1
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17  2  1  6
 10  3  1  0
 19 17  1  0
  1 20  1  0
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  5 23  1  0
  7 24  1  0
  7 25  1  0
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  8 27  1  0
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  9 29  1  0
 10 30  1  1
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 15 32  1  0
 15 33  1  0
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 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

  Mrv1652306242118093D          

 39 41  0  0  0  0            999 V2000
   -0.8860   -2.4814   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.0051   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.4410   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.9895    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    1.3503    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.1855   -0.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475    0.3882   -1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -0.0118    1.2000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3458    1.1216    1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.9789   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9190   -1.6743   -1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    1.7783    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.0256    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    1.1144    0.5694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0898    2.0364    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    1.1288    1.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.2719    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5545   -0.8666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2914   -1.0600    0.5508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4325   -2.7682   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.9325   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -2.9410    0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.3635    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -0.2175   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1274   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6457    1.4901   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.1458    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.9010    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.4334    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.6813    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -2.5446   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    1.7572    0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477    3.0504    0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0848    0.9537    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.2718   -1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9710    0.2626   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -0.6069    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.1627    0.6280 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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17  2  1  6  0  0  0
 10  3  1  0  0  0  0
 19 17  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  1  0  0  0
 11 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 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
 19 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(C([H])=C2C(=C(C([H])([H])[H])C3(C([H])([H])C3([H])[H])[C@@](O[H])(C2=O)C([H])([H])[H])[C@@]1([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-10-9(6-13(2,7-16)12(10)18)11(17)14(3,19)15(8)4-5-15/h6,12,16,18-19H,4-5,7H2,1-3H3/t12-,13+,14+/m1/s1

> <INCHI_KEY>
DDLLIYKVDWPHJI-RDBSUJKOSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.17245451440752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2'S,3'R,6'R)-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-7'-one

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
0.059551084333333476

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.911999888261189

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.73583987567909

> <JCHEM_PKA_STRONGEST_BASIC>
-2.804639199649273

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.6101

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
illudin S

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.8860   -2.4814   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.0051   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.4410   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.9895    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    1.3503    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.1855   -0.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475    0.3882   -1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -0.0118    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458    1.1216    1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.9789   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9190   -1.6743   -1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6317    3.0256    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0898    2.0364    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    1.1288    1.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.2719    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2914   -1.0600    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1668    2.3635    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -0.2175   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  3  4  1  0
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 19 39  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      -0.886  -2.481  -0.250  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.850  -1.005  -0.067  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.346  -0.441  -0.025  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.511   0.990   0.149  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.768   1.350   0.163  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.635   0.186  -0.003  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.447   0.388  -1.266  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.540  -0.012   1.200  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.346   1.122   1.367  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.723  -0.979  -0.125  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.919  -1.674  -1.320  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.712   1.778   0.277  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.632   3.026   0.131  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.004   1.114   0.569  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.090   2.036   0.006  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.161   1.129   1.965  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.114  -0.272   0.054  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.246  -0.555  -0.867  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.291  -1.060   0.551  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.433  -2.768  -1.176  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.115  -2.933  -0.323  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.357  -2.941   0.667  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.167   2.364   0.280  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.355  -0.218  -1.268  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.776   0.127  -2.120  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.646   1.490  -1.360  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.875  -0.146   2.080  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.168  -0.901   1.001  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.639   1.433   0.473  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.857  -1.681   0.747  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.338  -2.545  -1.147  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.085   1.757   0.358  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.848   3.050   0.387  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.013   2.095  -1.104  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.085   0.954   2.235  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.151  -1.272  -1.701  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.971   0.263  -1.071  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.000  -0.607   1.271  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.242  -2.163   0.628  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3   17                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8   10                                             
CONECT    7    6   24   25   26                                             
CONECT    8    6    9   27   28                                             
CONECT    9    8   29                                                       
CONECT   10    6   11    3   30                                             
CONECT   11   10   31                                                       
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14   32   33   34                                             
CONECT   16   14   35                                                       
CONECT   17   14   18    2   19                                             
CONECT   18   17   19   36   37                                             
CONECT   19   18   17   38   39                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    5                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -0.8860   -2.4814   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.0051   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.4410   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.9895    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    1.3503    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.1855   -0.0028 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4475    0.3882   -1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -0.0118    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458    1.1216    1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.9789   -0.1253 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9190   -1.6743   -1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    1.7783    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    3.0256    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    1.1144    0.5694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0898    2.0364    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    1.1288    1.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.2719    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5545   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914   -1.0600    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325   -2.7682   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154   -2.9325   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -2.9410    0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668    2.3635    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -0.2175   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1274   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6457    1.4901   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -0.1458    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.9010    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.4334    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8574   -1.6813    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -2.5446   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    1.7572    0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477    3.0504    0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133    2.0952   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    0.9537    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1505   -1.2718   -1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9710    0.2626   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -0.6069    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -2.1627    0.6280 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  2  0
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 19 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Illudin S	ChEMBL
Lampterol	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(2'S,3'R,6'R)-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-7'-one

Traditional Name

illudin S

CAS Registry Number

Not Available

SMILES

CC1=C2[C@@H](O)[C@](C)(CO)C=C2C(=O)[C@](C)(O)C11CC1

InChI Identifier

InChI=1S/C15H20O4/c1-8-10-9(6-13(2,7-16)12(10)18)11(17)14(3,19)15(8)4-5-15/h6,12,16,18-19H,4-5,7H2,1-3H3/t12-,13+,14+/m1/s1

InChI Key

DDLLIYKVDWPHJI-RDBSUJKOSA-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
Lampteromyces japonicus	LOTUS Database	35616633
Lamptreomyces japonicus	-	KNApSAcK
Omphalotus illudens	NPAtlas	14510611
Omphalotus olivascens	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Clitocybe illudens	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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
Cyclohexenone
Acyloin
Tertiary alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:5867 )
Illudane and protoilludane sesquiterpenoids (C09688 )
Terpenoids (C09688 )
Illudane and protoilludane sesquiterpenoids (LMPR0103590002 )

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	0.38	ALOGPS
logP	0.06	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.61 m³·mol⁻¹	ChemAxon
Polarizability	28.17 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

NPA019033

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003151

Chemspider ID

305173

KEGG Compound ID

C09688

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

Lehmann VK, Huang A, Ibanez-Calero S, Wilson GR, Rinehart KL: Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens. J Nat Prod. 2003 Sep;66(9):1257-8. doi: 10.1021/np030205w. [PubMed:14510611 ]
Goulielmaki E, Tsekrekou M, Batsiotos N, Ascensao-Ferreira M, Ledaki E, Stratigi K, Chatzinikolaou G, Topalis P, Kosteas T, Altmuller J, Demmers JA, Barbosa-Morais NL, Garinis GA: The splicing factor XAB2 interacts with ERCC1-XPF and XPG for R-loop processing. Nat Commun. 2021 May 26;12(1):3153. doi: 10.1038/s41467-021-23505-1. [PubMed:34039990 ]
Aoki S, Aboshi T, Onodera T, Kimura KI, Arai D, Iizuka Y, Murayama T: Omphaloprenol A: a new bioactive polyisoprenepolyol isolated from the mycelium of poisonous mushroom Omphalotus japonicus. Biosci Biotechnol Biochem. 2021 May 25;85(6):1364-1370. doi: 10.1093/bbb/zbab063. [PubMed:33851984 ]
Aoki S, Aboshi T, Shiono Y, Kimura KI, Murata T, Arai D, Iizuka Y, Murayama T: Constituents of the Fruiting Body of Poisonous Mushroom Omphalotus japonicus. Chem Pharm Bull (Tokyo). 2020;68(5):436-442. doi: 10.1248/cpb.c19-01009. [PubMed:32378541 ]
Apelt K, Zoutendijk I, Gout DY, Wondergem AP, van den Heuvel D, Luijsterburg MS: Human HMGN1 and HMGN2 are not required for transcription-coupled DNA repair. Sci Rep. 2020 Mar 9;10(1):4332. doi: 10.1038/s41598-020-61243-4. [PubMed:32152397 ]

Showing NP-Card for Illudin S (NP0004898)

MOL for NP0004898 (Illudin S)

3D MOL for NP0004898 (Illudin S)

3D SDF for NP0004898 (Illudin S)

3D-SDF for NP0004898 (Illudin S)

PDB for NP0004898 (Illudin S)

3D PDB for NP0004898 (Illudin S)

SMILES for NP0004898 (Illudin S)

INCHI for NP0004898 (Illudin S)

Structure for NP0004898 (Illudin S)

3D Structure for NP0004898 (Illudin S)