NP-MRD: Showing NP-Card for (2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0306587)

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Record Information

Version

2.0

Created at

2022-09-10 23:09:19 UTC

Updated at

2022-09-10 23:09:19 UTC

NP-MRD ID

NP0306587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Melleolide F belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. (2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate is found in Armillaria, Armillaria novae-zelandiae and Armillaria tabescens. (2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate was first documented in 2014 (PMID: 24906293). Based on a literature review a small amount of articles have been published on melleolide F (PMID: 31403293) (PMID: 26655762).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201092D          

 29 32  0  0  1  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1480    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.4336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897    0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.4642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2455    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -1.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6180   -1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -2.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -1.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8032   -1.6935    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
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  1  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 13 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    5.1092    2.0148   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3179    0.7892   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6426    0.3490   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9290   -0.7782    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2486   -1.2070    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9237   -1.4713    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -1.0112    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -1.6873    1.3316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967    0.1089   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477    0.6062   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7056    1.6638   -0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983    0.0313    0.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    0.5993    0.1873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2533    0.9518    1.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    0.8360    0.4542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4923    2.0841   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712    0.4084    1.1319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9376    1.1588    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7313    0.4770   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0979   -0.0068    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9940    1.3389   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.7871   -0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1376   -0.9998    0.7253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0145   -1.9213    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -1.5543    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -2.6283    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062   -3.8172    0.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6227   -0.2015   -0.2520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7616   -0.0448   -1.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0757    2.4074   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4722    1.8621   -2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096    2.8251   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4654    0.8597   -1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9934   -0.7206   -0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482   -2.3463    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7997   -2.5118    1.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810    1.5506   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.1763    2.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    1.9896    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1198    1.9122   -1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807    2.5277   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8577    2.8911    0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4607    0.3032    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    0.9993    1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    2.2426    0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4492   -0.8274   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0670   -0.3685    1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8478    0.8241    0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148    1.1930   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8250    2.3950   -1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142    1.0909   -2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4172   -0.5761   -1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6568   -1.6375   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -1.3075    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -2.9598    0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -2.7101   -0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -2.3106    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -4.2327    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813   -0.8422   -2.1129 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  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  1  6
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  6
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  1
 24 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
M  END


  Mrv1652309112201092D          

 29 32  0  0  1  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1480    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.4336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897    0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.4642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2455    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -1.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6180   -1.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -1.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -2.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -1.1322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8032   -1.6935    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
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  1  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 13 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0306587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)O[C@@H]1C[C@]2(C)[C@H]3CC(C)(C)C[C@H]3C=C(CO)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/c1-12-5-15(25)7-17(26)19(12)20(27)29-18-10-22(4)16-9-21(2,3)8-13(16)6-14(11-24)23(18,22)28/h5-7,13,16,18,24-26,28H,8-11H2,1-4H3/t13-,16+,18-,22-,23+/m1/s1

> <INCHI_KEY>
PAOHIYZPMWDBLO-IDOJSZHESA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.487

> <EXACT_MASS>
402.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.83596235253276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.7936817123333317

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.55423122424302

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.69752185370273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7659305962148295

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
109.02969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.132  -3.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.180  -2.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.681  -2.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.729  -1.538   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.230  -1.881   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.275  -0.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.774   0.277   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.321   1.749   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.726  -0.852   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.225  -0.509   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.771   0.963   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.177  -1.637   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.324  -1.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.143   0.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.447  -0.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.901   0.662   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986  -0.867   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.499  -3.161   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   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   28                                             
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   13   15   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₆

Average Mass

402.4870 Da

Monoisotopic Mass

402.20424 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(=O)O[C@@H]1C[C@]2(C)[C@H]3CC(C)(C)C[C@H]3C=C(CO)[C@]12O

InChI Identifier

InChI=1S/C23H30O6/c1-12-5-15(25)7-17(26)19(12)20(27)29-18-10-22(4)16-9-21(2,3)8-13(16)6-14(11-24)23(18,22)28/h5-7,13,16,18,24-26,28H,8-11H2,1-4H3/t13-,16+,18-,22-,23+/m1/s1

InChI Key

PAOHIYZPMWDBLO-IDOJSZHESA-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
Armillaria	LOTUS Database	35616633
Armillaria novae-zelandiae	LOTUS Database	35616633
Armillaria tabescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
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
M-cresol
Resorcinol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
Toluene
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
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	3.79	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.03 m³·mol⁻¹	ChemAxon
Polarizability	43.84 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

C00056548

Chemspider ID

8962608

KEGG Compound ID

Not Available

BioCyc ID

CPD-20140

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10787295

PDB ID

Not Available

ChEBI ID

167712

Good Scents ID

Not Available

References

General References

Bohnert M, Nutzmann HW, Schroeckh V, Horn F, Dahse HM, Brakhage AA, Hoffmeister D: Cytotoxic and antifungal activities of melleolide antibiotics follow dissimilar structure-activity relationships. Phytochemistry. 2014 Sep;105:101-8. doi: 10.1016/j.phytochem.2014.05.009. Epub 2014 Jun 3. [PubMed:24906293 ]
Shimoda K, Yamaoka Y, Yoo D, Yamada KI, Takikawa H, Takasu K: Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and Echinocidins. J Org Chem. 2019 Sep 6;84(17):11014-11024. doi: 10.1021/acs.joc.9b01589. Epub 2019 Aug 12. [PubMed:31403293 ]
Wick J, Heine D, Lackner G, Misiek M, Tauber J, Jagusch H, Hertweck C, Hoffmeister D: A Fivefold Parallelized Biosynthetic Process Secures Chlorination of Armillaria mellea (Honey Mushroom) Toxins. Appl Environ Microbiol. 2015 Dec 11;82(4):1196-1204. doi: 10.1128/AEM.03168-15. Print 2016 Feb 15. [PubMed:26655762 ]
LOTUS database [Link]

Showing NP-Card for (2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0306587)

MOL for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0306587 ((2r,2as,4as,7as,7br)-2a-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)