NP-MRD: Showing NP-Card for 3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate (NP0256414)

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Record Information

Version

2.0

Created at

2022-09-07 21:14:05 UTC

Updated at

2022-09-07 21:14:05 UTC

NP-MRD ID

NP0256414

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

Description

Armillarin 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. Armillarin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Armillarin has been detected, but not quantified in, mushrooms. This could make armillarin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311042D          

 30 33  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16  8  2  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23  4  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
 24 23  1  0  0  0  0
 25 12  2  0  0  0  0
 26 18  1  0  0  0  0
 27 21  2  0  0  0  0
 28 24  1  0  0  0  0
 29  5  1  0  0  0  0
 29 16  1  0  0  0  0
 30 19  1  0  0  0  0
 30 21  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    8.8088    0.6637    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9540   -0.0456    0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5850    0.1227    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6947   -0.5327   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353   -0.3679   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953   -1.0968   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7990    0.5066    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721    0.7180    0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810    1.5028    1.3027 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    0.0712   -0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.2565   -0.2398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6586    0.6205   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365   -0.4104   -1.1438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0704   -1.3518   -2.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9409    0.2751   -0.6530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2384   -0.4494   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2174    0.4632   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4081    1.6837   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5399   -0.1955    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4753    0.7666    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    0.5578    0.8027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4308   -0.5265    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3970   -1.2416    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941   -2.2930    2.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.9728    1.6609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003   -0.9526   -0.1319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1981   -2.1371   -0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    1.1886    1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180    2.0828    2.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681    0.9873    1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8602    0.3742    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6853    1.7618    0.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6333    0.3416    1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0780   -1.2264   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373   -0.4109   -2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -1.8052   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734   -1.7526   -0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1794    0.9905    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158    1.6517   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    0.3371   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1442   -1.6399   -2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4938   -2.2704   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7776   -0.8136   -2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293    1.2648   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -0.4233   -1.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2591   -1.4323   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4545    2.0472   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1922    1.4375   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7455    2.5206   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0077    0.2551    0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2011    0.0738   -0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4697   -1.2999    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8274    0.0163    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920    1.7916    1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877    1.5097    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.7079    2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254   -2.4978    3.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580   -1.9511   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    2.4394    2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7479    1.5250    1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 30  2  0
 30 28  1  0
 28 29  1  0
 28  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
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 23 26  1  0
 26 27  1  6
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 26 11  1  0
 26 13  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 60  1  0
 29 59  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  6
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  6
 22 56  1  0
 24 57  1  0
 27 58  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  4 34  1  0
M  END


  Mrv0541 05061311042D          

 30 33  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16  8  2  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23  4  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
 24 23  1  0  0  0  0
 25 12  2  0  0  0  0
 26 18  1  0  0  0  0
 27 21  2  0  0  0  0
 28 24  1  0  0  0  0
 29  5  1  0  0  0  0
 29 16  1  0  0  0  0
 30 19  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256414

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C=C(C=O)C23O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O6/c1-13-6-16(29-5)8-18(26)20(13)21(27)30-19-11-23(4)17-10-22(2,3)9-14(17)7-15(12-25)24(19,23)28/h6-8,12,14,17,19,26,28H,9-11H2,1-5H3

> <INCHI_KEY>
ISKWRTCZWOXOOF-UHFFFAOYSA-N

> <FORMULA>
C24H30O6

> <MOLECULAR_WEIGHT>
414.4914

> <EXACT_MASS>
414.204238692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31187819442127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.253423271666666

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.797799551113524

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.762775387266155

> <JCHEM_PKA_STRONGEST_BASIC>
-3.762219142737824

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
112.52909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.726   2.792   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.684   0.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.087  -1.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.631   0.535   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.538  -2.409   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.499   0.483   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   29                                                            
CONECT    6   13   16                                                       
CONECT    7   14   15                                                       
CONECT    8   16   18                                                       
CONECT    9   14   22                                                       
CONECT   10   17   22                                                       
CONECT   11   19   23                                                       
CONECT   12   15   25                                                       
CONECT   13    1    6   20                                                  
CONECT   14    7    9   17                                                  
CONECT   15    7   12   24                                                  
CONECT   16    6    8   29                                                  
CONECT   17   10   14   23                                                  
CONECT   18    8   20   26                                                  
CONECT   19   11   24   30                                                  
CONECT   20   13   18   21                                                  
CONECT   21   20   27   30                                                  
CONECT   22    2    3    9   10                                             
CONECT   23    4   11   17   24                                             
CONECT   24   15   19   23   28                                             
CONECT   25   12                                                            
CONECT   26   18                                                            
CONECT   27   21                                                            
CONECT   28   24                                                            
CONECT   29    5   16                                                       
CONECT   30   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
3-Formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₃₀O₆

Average Mass

414.4914 Da

Monoisotopic Mass

414.20424 Da

IUPAC Name

3-formyl-2a-hydroxy-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

3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C=C(C=O)C23O)C(C)=C1

InChI Identifier

InChI=1S/C24H30O6/c1-13-6-16(29-5)8-18(26)20(13)21(27)30-19-11-23(4)17-10-22(2,3)9-14(17)7-15(12-25)24(19,23)28/h6-8,12,14,17,19,26,28H,9-11H2,1-5H3

InChI Key

ISKWRTCZWOXOOF-UHFFFAOYSA-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
Methoxyphenol
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Phenoxy compound
M-cresol
Anisole
Methoxybenzene
Benzoyl
Phenol ether
Phenol
Toluene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Vinylogous acid
Cyclobutanol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Aldehyde
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
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	3.79	ALOGPS
logP	4.25	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.53 m³·mol⁻¹	ChemAxon
Polarizability	45.31 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

HMDB0039380

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018945

KNApSAcK ID

Not Available

Chemspider ID

26502956

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53462326

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate (NP0256414)

MOL for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D MOL for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D SDF for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D-SDF for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

PDB for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D PDB for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

SMILES for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

INCHI for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

Structure for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)

3D Structure for NP0256414 (3-formyl-2a-hydroxy-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate)