NP-MRD: Showing NP-Card for [(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate (NP0290136)

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Record Information

Version

2.0

Created at

2022-09-09 20:40:54 UTC

Updated at

2022-09-09 20:40:54 UTC

NP-MRD ID

NP0290136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate

Description

[(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate 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. [(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate is found in Desarmillaria tabescens. Based on a literature review very few articles have been published on [(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092222402D          

 30 33  0  0  1  0            999 V2000
   -0.1163    1.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550    2.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    2.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    2.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    3.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    3.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225    4.4744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550    3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    3.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6676   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    6.1147   -0.0385   -1.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6842    0.6204   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536    1.3119    0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3166    1.9448    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2913    2.6363    1.9092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193    1.9116    1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    1.2261    0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7722    1.1889    1.3213 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    0.5763   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3940   -0.1424   -1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6594   -0.7403   -2.1439 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555   -0.2082   -0.6602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084   -0.9133   -1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2479   -0.8622   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -0.3183   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -0.2549   -0.9620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3601    0.9713   -1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566    0.8854   -0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1182    2.2022   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4082   -0.1940   -0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358    0.3671    0.9784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6537    1.4556    1.8551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    0.0159    0.5378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6928   -1.1035    1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5881   -0.8566    2.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.4958    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7818   -2.8866    0.5803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6481   -3.5851   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -1.4224    0.5272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6737   -1.0905    1.3649 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2015    0.1001   -2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555    0.4342   -2.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9476   -1.1349   -1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6801    1.3505   -0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292    3.6192    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    2.4239    2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    1.6494    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1154   -0.5024   -2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -1.9881   -1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    0.0659   -2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1903   -1.1348   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    1.8529   -1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    0.9437   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6290    2.1540    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3313    2.9881    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8587    2.3751   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4559    0.0486   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1854   -1.1743   -0.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820   -0.4147   -1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2975   -0.4485    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    2.1626    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885    0.9115    0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    0.1301    2.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -0.8796    3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -1.6794    3.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -2.6381    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -3.0736    1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2108   -3.3921    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0682   -3.1422   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -1.8081    2.0690 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  1
  9  2  1  0
 29 14  1  0
 23 16  1  0
 29 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  1
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 23 52  1  6
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  1
 28 59  1  0
 30 60  1  0
M  END


  Mrv1652309092222402D          

 30 33  0  0  1  0            999 V2000
   -0.1163    1.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550    2.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    2.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    2.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    2.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    3.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    3.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225    4.4744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550    3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    3.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6676   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0290136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)OCC1=C[C@@H]2CC(C)(C)[C@H](O)[C@H]2[C@@]2(C)C[C@@H](O)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-11-5-14(24)7-15(25)17(11)20(28)30-10-13-6-12-8-21(2,3)19(27)18(12)22(4)9-16(26)23(13,22)29/h5-7,12,16,18-19,24-27,29H,8-10H2,1-4H3/t12-,16-,18+,19-,22-,23+/m1/s1

> <INCHI_KEY>
OEBGQVIRXPDBGY-SDEDHOBLSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.93198352129545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_LOGP>
2.6408243753333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.555840783486394

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.699307889516506

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0342443644107737

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
110.4682

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.217   3.021   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.036   4.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.575   4.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.394   5.572   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.933   5.515   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.674   6.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.135   6.991   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.415   8.352   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.316   5.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.223   5.744   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.943   7.105   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.986   0.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.846  -2.038   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.499   0.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.376   1.013   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.874   1.356   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23   25   26   29                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   24   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(2R,2AS,4as,7R,7ar,7BR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

[(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

[(2R,2aS,4aS,7R,7aR,7bR)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OCC1=C[C@@H]2CC(C)(C)[C@H](O)[C@H]2[C@@]2(C)C[C@@H](O)[C@@]12O

InChI Identifier

InChI=1S/C23H30O7/c1-11-5-14(24)7-15(25)17(11)20(28)30-10-13-6-12-8-21(2,3)19(27)18(12)22(4)9-16(26)23(13,22)29/h5-7,12,16,18-19,24-27,29H,8-10H2,1-4H3/t12-,16-,18+,19-,22-,23+/m1/s1

InChI Key

OEBGQVIRXPDBGY-SDEDHOBLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Desarmillaria tabescens	LOTUS Database	35616633

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

Illudane sesquiterpenoid
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Resorcinol
M-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Toluene
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.64	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.47 m³·mol⁻¹	ChemAxon
Polarizability	44.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163029499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate (NP0290136)

MOL for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0290136 ([(2r,2as,4as,7r,7ar,7br)-2,2a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methyl 2,4-dihydroxy-6-methylbenzoate)