NP-MRD: Showing NP-Card for (2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate (NP0286931)

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Record Information

Version

2.0

Created at

2022-09-09 15:44:47 UTC

Updated at

2022-09-09 15:44:47 UTC

NP-MRD ID

NP0286931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5'-O-methylmelledonal 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. Based on a literature review very few articles have been published on 5'-O-methylmelledonal.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092217442D          

 32 35  0  0  1  0            999 V2000
   -4.1164   -1.7959    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
   -3.0691   -0.8238    0.0000 C   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 C   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  1  0  0  0  0  0  0  0  0  0
    3.1041    0.9407    0.0000 O   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
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423   -1.8493    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 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  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 11 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
  7 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    7.9807   -0.7739    2.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8037   -0.8327    0.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089   -0.6282    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826   -0.6749   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065   -0.4742   -1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480   -0.5420   -2.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.2236   -0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -0.0216   -1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516   -0.0753   -2.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4503    0.2344   -0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490    0.4095   -1.0684 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5462    1.6560   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    0.8124   -1.0146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9887    0.7758   -2.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    1.0828   -0.2628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0834    0.1598   -0.6969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6734   -1.1460   -0.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0401    0.1471    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1768    1.1070    0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6754   -1.2136    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730    0.6226    1.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    0.9843    1.2270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5789    2.2333    1.7660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8662    0.0188    1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961   -0.5973    0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626   -1.5195    1.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7683   -2.1135    0.7769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9550   -0.3696   -0.5584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1029   -1.5200   -1.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1466   -0.1744    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.0637    1.7175 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4451   -0.3788    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7852    0.2581    2.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2605   -1.4265    2.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -1.0474    2.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0954   -0.8678   -1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -1.3633   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850    0.4358   -3.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458   -0.7176   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2599    0.3396   -2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715    1.8865    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    2.5043   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389    1.5157   -3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -0.2372   -2.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215    1.0163   -2.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3304    2.1254   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6070    0.4822   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1575   -1.6198   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8371    2.1690    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0683    0.9462    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4360    1.0147   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7114   -1.2507    0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1178   -2.0288    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7221   -1.4197    1.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -0.1928    2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8140    1.4984    2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    2.9286    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400   -0.1982    2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -1.7040    2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -1.9688   -1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2366    0.2334    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6205   -0.3400    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 25 28  1  0
 28 29  1  6
  7 30  1  0
 30 31  1  0
 30 32  2  0
 32  3  1  0
 28 11  1  0
 28 13  1  0
 22 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  1
 16 47  1  6
 17 48  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 23 57  1  0
 24 58  1  0
 26 59  1  0
 29 60  1  0
 31 61  1  0
 32 62  1  0
M  END

  Mrv1652309092217442D          

 32 35  0  0  1  0            999 V2000
   -4.1164   -1.7959    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
   -3.0691   -0.8238    0.0000 C   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 C   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  1  0  0  0  0  0  0  0  0  0
    3.1041    0.9407    0.0000 O   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
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423   -1.8493    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 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  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 11 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
  7 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4[C@@H](O)C(C)(C)C[C@@]4(O)C=C(C=O)[C@]23O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,10,16,18-19,26-27,29-30H,9,11H2,1-5H3/t16-,18-,19-,22-,23+,24+/m1/s1

> <INCHI_KEY>
PETDNGRBYPTDNI-QSNWBFGMSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.98623637307254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.9828228966666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.740594418512252

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.762718860082378

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0722485964669746

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
115.39689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aR,7R,7aS,7bR)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-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      -7.684  -3.352   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.230  -1.881   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.729  -1.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.275  -0.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.774   0.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.321   1.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.726  -0.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.225  -0.509   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.771   0.963   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.177  -1.637   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.324  -1.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.143   0.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.447  -0.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.901   0.662   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986  -0.867   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.794   1.756   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.564  -3.507   0.000  0.00  0.00           O+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
HETATM   30  C   UNK     0      -3.180  -2.323   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.132  -3.452   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.681  -2.666   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   28                                             
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   15   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   11   13   29                                             
CONECT   29   28                                                            
CONECT   30    7   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4960 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4[C@@H](O)C(C)(C)C[C@@]4(O)C=C(C=O)[C@]23O)C(O)=C1

InChI Identifier

InChI=1S/C24H30O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,10,16,18-19,26-27,29-30H,9,11H2,1-5H3/t16-,18-,19-,22-,23+,24+/m1/s1

InChI Key

PETDNGRBYPTDNI-QSNWBFGMSA-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
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Salicylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Phenoxy compound
M-cresol
Anisole
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
Toluene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Ether
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	1.98	ChemAxon
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.4 m³·mol⁻¹	ChemAxon
Polarizability	45.99 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

C00056483

Chemspider ID

159527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

183472

PDB ID

Not Available

ChEBI ID

185238

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate (NP0286931)

MOL for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D MOL for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D SDF for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D-SDF for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

PDB for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D PDB for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

SMILES for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

INCHI for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

Structure for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D Structure for NP0286931 ((2r,2as,4ar,7r,7as,7br)-3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)