NP-MRD: Showing NP-Card for (2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0328068)

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Record Information

Version

2.0

Created at

2022-09-12 11:12:11 UTC

Updated at

2022-09-12 11:12:11 UTC

NP-MRD ID

NP0328068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

13-Hydroxydihydromelleolide 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,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate was first documented in 2015 (PMID: 25524590). Based on a literature review very few articles have been published on 13-hydroxydihydromelleolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213122D          

 30 33  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  2  0  0  0  0  0  0  0  0  0
    3.5165   -1.8786    0.0000 O   0  0  0  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
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 13 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    3.0099    0.7081    1.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817    0.7012    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4677    0.9121    1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6748    0.9296    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8430    1.1456    1.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7306    0.7357   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5384    0.5224   -1.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905    0.3373   -2.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3225    0.5032   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0778    0.2961   -1.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.1125   -2.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646    0.2784   -0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    0.1011   -1.1965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2278    1.3347   -1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3885    0.3777   -1.1587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8475    0.2629   -2.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    0.6276   -0.2457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5834   -0.4362   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3965   -0.3136    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7029   -1.7036    1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7304    0.3469    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167    0.4995    1.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.6881    1.2035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6754    1.8500    1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -0.5318    1.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379   -1.1312    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111   -2.3466    1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -2.6257    2.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457   -0.7238   -0.7390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6772   -1.8279   -1.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.5593    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -0.2677    1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300    0.9047    2.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    1.0703    2.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7261    1.1579    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6794    0.7470   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    0.1715   -3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710   -0.0153   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    2.0843   -1.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0531    1.7170    0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    0.8616   -3.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.5314   -2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7251   -0.8021   -2.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9956    1.5911   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -0.1967   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494   -1.4456   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7796   -1.9575    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -2.4821    0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4444   -1.7151    2.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6088    1.1622   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.7357    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3814   -0.4450    0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5398   -0.0196    2.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174    1.5054    1.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182    2.6538    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5054   -0.9000    2.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108   -3.2207    0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2003   -2.1832    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -1.9018    2.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -2.5311   -1.4565 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  6
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  6
  9  2  1  0
 29 13  1  0
 29 15  1  0
 23 17  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  6
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
M  END


  Mrv1652309122213122D          

 30 33  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  2  0  0  0  0  0  0  0  0  0
    3.5165   -1.8786    0.0000 O   0  0  0  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
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 13 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328068

> <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@@]3(O)C=C(CO)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-12-5-14(25)6-15(26)18(12)19(27)30-17-9-21(4)16-8-20(2,3)11-22(16,28)7-13(10-24)23(17,21)29/h5-7,16-17,24-26,28-29H,8-11H2,1-4H3/t16-,17-,21-,22+,23+/m1/s1

> <INCHI_KEY>
ABFOJGYAILKEJB-MTJRIOAFSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.96911125526339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,4aR,7aR,7bR)-2a,4a-dihydroxy-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>
2.7123356773333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.554032105589004

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697519014801244

> <JCHEM_PKA_STRONGEST_BASIC>
-2.771949516122305

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
110.48079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  O   UNK     0       6.564  -3.507   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   30  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   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   29                                             
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   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   13   15   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

(2R,2aS,4aR,7aR,7bR)-2a,4a-dihydroxy-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,4aR,7aR,7bR)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,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@@]3(O)C=C(CO)[C@]12O

InChI Identifier

InChI=1S/C23H30O7/c1-12-5-14(25)6-15(26)18(12)19(27)30-17-9-21(4)16-8-20(2,3)11-22(16,28)7-13(10-24)23(17,21)29/h5-7,16-17,24-26,28-29H,8-11H2,1-4H3/t16-,17-,21-,22+,23+/m1/s1

InChI Key

ABFOJGYAILKEJB-MTJRIOAFSA-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

Not Available

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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Cyclic alcohol
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen 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	2.71	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-2.8	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	110.48 m³·mol⁻¹	ChemAxon
Polarizability	43.97 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

C00021467

Chemspider ID

26346325

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54584947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kobori H, Sekiya A, Suzuki T, Choi JH, Hirai H, Kawagishi H: Bioactive sesquiterpene aryl esters from the culture broth of Armillaria sp. J Nat Prod. 2015 Jan 23;78(1):163-7. doi: 10.1021/np500322t. Epub 2014 Dec 19. [PubMed:25524590 ]
LOTUS database [Link]

Showing NP-Card for (2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0328068)

MOL for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0328068 ((2r,2as,4ar,7ar,7br)-2a,4a-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)