NP-MRD: Showing NP-Card for (2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0184865)

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Record Information

Version

2.0

Created at

2022-09-04 00:06:16 UTC

Updated at

2022-09-04 00:06:16 UTC

NP-MRD ID

NP0184865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202062D          

 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  2  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  1  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
    3.8695   -1.0521    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
    4.7863   -0.4368    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
    3.2455    0.1279    0.0000 C   0  0  2  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
  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
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 13 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 18 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    5.5111   -1.5479   -1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929   -0.3927   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8536    0.0741    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9701    1.1411    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2066    1.6495    1.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534    1.7789    1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5688    1.3178    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094    2.0078    1.6004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486    0.2391    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1506   -0.2639   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -1.2769   -0.9610 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    0.2709    0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7427   -0.3001   -0.2541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0846    0.8249   -0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2378   -0.0086   -0.5753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3487   -1.2075   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732    0.4244    0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1393   -0.8852    0.4967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2349   -1.7497    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511   -1.4969    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -2.4454    2.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5976   -3.4636    2.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -0.3579    0.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4210    0.7659    1.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2843   -0.2693    1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8036    0.6552    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6880   -0.1571   -0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4722    1.8497    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5630    1.0389   -0.7335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6957    0.6716   -2.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -2.3990   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5637   -1.8890   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383   -1.3503   -2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7480   -0.4183   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602    2.3697    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9196    2.6209    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5736    1.8537    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959   -1.1521   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608    0.8140   -1.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    1.7961   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135   -1.1279   -2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -2.1315   -0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3490   -1.2388   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    1.0186    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566   -1.4328   -0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734   -2.6442    1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484   -2.2774    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148    0.5247    2.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -0.9537    1.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9254    0.4097    2.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1437   -0.6392   -1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1783   -0.9834   -0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4753    0.5095   -1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0031    2.8129    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5500    1.8227    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4558    1.7630    1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4954    2.1486   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588    1.2867   -2.6148 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 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 20 23  1  0
 23 24  1  1
  9  2  1  0
 23 13  1  0
 23 15  1  0
 29 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  1
 18 45  1  6
 25 49  1  0
 25 50  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  6
 30 58  1  0
 19 46  1  0
 21 47  1  0
 24 48  1  0
M  END


  Mrv1652309042202062D          

 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  2  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  1  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
    3.8695   -1.0521    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
    4.7863   -0.4368    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
    3.2455    0.1279    0.0000 C   0  0  2  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
  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
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 13 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 18 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0184865

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O7/c1-11-5-14(25)7-15(26)17(11)20(28)30-16-9-22(4)18-12(8-21(2,3)19(18)27)6-13(10-24)23(16,22)29/h5-7,10,12,16,18-19,25-27,29H,8-9H2,1-4H3/t12-,16+,18+,19+,22+,23+/m0/s1

> <INCHI_KEY>
VNRLQDGXGABKPC-PKPCJMEJSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.47

> <EXACT_MASS>
416.183503242

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.203772606132304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aR,4aR,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-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>
2.9546718786666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.553480130605575

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697501334604752

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0342593569572927

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
109.48529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aR,4aR,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-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                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.499  -3.161   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.794   1.756   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   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   29                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   13   15   24                                             
CONECT   24   23                                                            
CONECT   25   18   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   17   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,2AR,4ar,7R,7as,7BR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₃H₂₈O₇

Average Mass

416.4700 Da

Monoisotopic Mass

416.18350 Da

IUPAC Name

(2R,2aR,4aR,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-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,2aR,4aR,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-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]3[C@H](CC(C)(C)[C@@H]3O)C=C(C=O)[C@@]12O

InChI Identifier

InChI=1S/C23H28O7/c1-11-5-14(25)7-15(26)17(11)20(28)30-16-9-22(4)18-12(8-21(2,3)19(18)27)6-13(10-24)23(16,22)29/h5-7,10,12,16,18-19,25-27,29H,8-9H2,1-4H3/t12-,16+,18+,19+,22+,23+/m0/s1

InChI Key

VNRLQDGXGABKPC-PKPCJMEJSA-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
Resorcinol
M-cresol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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	2.95	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.49 m³·mol⁻¹	ChemAxon
Polarizability	44.2 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

163008957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate (NP0184865)

MOL for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0184865 ((2r,2ar,4ar,7r,7as,7br)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate)