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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:46 UTC

Update Date

2022-03-07 02:53:04 UTC

HMDB ID

HMDB0031674

Secondary Accession Numbers

HMDB31674

Metabolite Identification

Common Name

Armillarinin

Description

Armillarinin 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 a small amount of articles have been published on Armillarinin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 05061306042D          

 32 35  0  0  0  0            999 V2000
   -0.5788    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8712    0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874    2.0658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 23  7  1  0  0  0  0
 23 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 10  2  0  0  0  0
 27 14  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31  5  1  0  0  0  0
 31 15  1  0  0  0  0
 32 17  1  0  0  0  0
 32 20  1  0  0  0  0
M  END

HMDB0031674
     RDKit          3D
Armillarinin
 61 64  0  0  0  0  0  0  0  0999 V2000
    8.1859    1.9799    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6987    1.0231   -0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3643    0.6586   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    1.2570   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    0.9165   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285    1.5513    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6821   -0.0408   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.4579   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.3418   -2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.0236   -0.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.3942   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6943   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656    0.4135    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    1.4817    1.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    0.2706    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7748    1.2814    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.5208    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773    1.1086   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9208    0.4211    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -0.8646   -0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5068   -1.0493    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089   -1.3932    2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.1883    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -2.0774    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -3.2882    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6910   -3.2538    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.8153    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -0.8618    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -0.6425   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722   -1.6650   -2.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -0.2844   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0988   -1.0779   -2.9152 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1734    2.3634   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    2.8696    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    1.4931    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7316    2.0111    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    1.4033    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -1.1667   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.4194   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053    1.6999   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    1.1559    1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148    2.4730    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.5417    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.5490    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9666    2.1849    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796    1.5640   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455    0.3253   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8361    1.5193   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300    1.9151   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    0.6641    2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -0.5856    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7876    1.1426    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -0.7666   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057   -1.6296   -0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646   -1.0991    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -3.1674    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177   -4.2579    0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -0.6735    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050   -1.9951   -3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100   -2.5972   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -1.2612   -3.6827 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  0
 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
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31  3  1  0
 27 11  1  0
 27 13  1  0
 21 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 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
 22 55  1  0
 23 56  1  0
 25 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
M  END

  Mrv0541 05061306042D          

 32 35  0  0  0  0            999 V2000
   -0.5788    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8712    0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874    2.0658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 23  7  1  0  0  0  0
 23 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 10  2  0  0  0  0
 27 14  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31  5  1  0  0  0  0
 31 15  1  0  0  0  0
 32 17  1  0  0  0  0
 32 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031674

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO7/c1-12-18(14(27)6-15(31-5)19(12)25)20(28)32-17-9-22(4)16-8-21(2,3)11-23(16,29)7-13(10-26)24(17,22)30/h6-7,10,16-17,27,29-30H,8-9,11H2,1-5H3

> <INCHI_KEY>
XOGUZUVXPLTDMB-UHFFFAOYSA-N

> <FORMULA>
C24H29ClO7

> <MOLECULAR_WEIGHT>
464.936

> <EXACT_MASS>
464.160180989

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.08896430983783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.7761219129999994

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.759490633044269

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.32536236365188

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2083614593839442

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
118.78499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031674
     RDKit          3D
Armillarinin
 61 64  0  0  0  0  0  0  0  0999 V2000
    8.1859    1.9799    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6987    1.0231   -0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3643    0.6586   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    1.2570   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    0.9165   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285    1.5513    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6821   -0.0408   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.4579   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.3418   -2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.0236   -0.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.3942   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6943   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656    0.4135    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    1.4817    1.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    0.2706    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7748    1.2814    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.5208    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773    1.1086   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9208    0.4211    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -0.8646   -0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5068   -1.0493    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089   -1.3932    2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.1883    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -2.0774    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -3.2882    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6910   -3.2538    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.8153    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -0.8618    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -0.6425   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722   -1.6650   -2.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -0.2844   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0988   -1.0779   -2.9152 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1734    2.3634   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    2.8696    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    1.4931    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7316    2.0111    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    1.4033    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -1.1667   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.4194   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053    1.6999   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    1.1559    1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148    2.4730    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.5417    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.5490    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9666    2.1849    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796    1.5640   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455    0.3253   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8361    1.5193   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300    1.9151   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    0.6641    2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -0.5856    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7876    1.1426    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -0.7666   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057   -1.6296   -0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646   -1.0991    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -3.1674    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177   -4.2579    0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -0.6735    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050   -1.9951   -3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100   -2.5972   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -1.2612   -3.6827 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  0
 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
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31  3  1  0
 27 11  1  0
 27 13  1  0
 21 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 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
 22 55  1  0
 23 56  1  0
 25 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
M  END

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      -1.080   3.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.986   0.534   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.226   0.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.224  -0.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.128   2.042   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.722  -0.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.677   1.256   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.675   0.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.630   2.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.173   0.227   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.499   0.528   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      -4.083   3.856   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.269  -2.031   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.280  -1.245   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.616   3.225   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.178   1.599   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   31                                                            
CONECT    6   14   15                                                       
CONECT    7   13   23                                                       
CONECT    8   16   21                                                       
CONECT    9   17   22                                                       
CONECT   10   13   26                                                       
CONECT   11   21   23                                                       
CONECT   12    1   18   19                                                  
CONECT   13    7   10   24                                                  
CONECT   14    6   18   27                                                  
CONECT   15    6   19   31                                                  
CONECT   16    8   22   23                                                  
CONECT   17    9   24   32                                                  
CONECT   18   12   14   20                                                  
CONECT   19   12   15   25                                                  
CONECT   20   18   28   32                                                  
CONECT   21    2    3    8   11                                             
CONECT   22    4    9   16   24                                             
CONECT   23    7   11   16   29                                             
CONECT   24   13   17   22   30                                             
CONECT   25   19                                                            
CONECT   26   10                                                            
CONECT   27   14                                                            
CONECT   28   20                                                            
CONECT   29   23                                                            
CONECT   30   24                                                            
CONECT   31    5   15                                                       
CONECT   32   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0031674
HETATM    1  C1  UNL     1       8.186   1.980   0.061  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.699   1.023  -0.837  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.364   0.659  -0.924  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.464   1.257  -0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.090   0.916  -0.147  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.228   1.551   0.712  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.682  -0.041  -1.064  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.299  -0.458  -1.191  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.961  -1.342  -2.047  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.249   0.024  -0.446  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.081  -0.394  -0.587  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.131   0.694  -0.641  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.466   0.414   0.808  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.791   1.482   1.668  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.888   0.271   1.166  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.775   1.281   0.433  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.057   0.521   0.208  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.877   1.109  -0.918  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.921   0.421   1.424  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.524  -0.865  -0.183  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.507  -1.049   0.949  1.00  0.00           C  
HETATM   22  O5  UNL     1      -4.309  -1.393   2.071  1.00  0.00           O  
HETATM   23  C18 UNL     1      -2.642  -2.188   0.709  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.349  -2.077   0.630  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.543  -3.288   0.383  1.00  0.00           C  
HETATM   26  O6  UNL     1       0.691  -3.254   0.297  1.00  0.00           O  
HETATM   27  C21 UNL     1      -0.657  -0.815   0.772  1.00  0.00           C  
HETATM   28  O7  UNL     1       0.339  -0.862   1.777  1.00  0.00           O  
HETATM   29  C22 UNL     1       4.635  -0.643  -1.909  1.00  0.00           C  
HETATM   30  C23 UNL     1       4.172  -1.665  -2.882  1.00  0.00           C  
HETATM   31  C24 UNL     1       5.959  -0.284  -1.826  1.00  0.00           C  
HETATM   32 CL1  UNL     1       7.099  -1.078  -2.915  1.00  0.00          CL  
HETATM   33  H1  UNL     1       9.173   2.363  -0.323  1.00  0.00           H  
HETATM   34  H2  UNL     1       7.522   2.870   0.162  1.00  0.00           H  
HETATM   35  H3  UNL     1       8.313   1.493   1.047  1.00  0.00           H  
HETATM   36  H4  UNL     1       5.732   2.011   0.640  1.00  0.00           H  
HETATM   37  H5  UNL     1       2.273   1.403   0.768  1.00  0.00           H  
HETATM   38  H6  UNL     1      -0.180  -1.167  -1.383  1.00  0.00           H  
HETATM   39  H7  UNL     1      -1.920   0.419  -1.373  1.00  0.00           H  
HETATM   40  H8  UNL     1      -0.705   1.700  -0.844  1.00  0.00           H  
HETATM   41  H9  UNL     1       0.224   1.156   1.979  1.00  0.00           H  
HETATM   42  H10 UNL     1      -0.815   2.473   1.209  1.00  0.00           H  
HETATM   43  H11 UNL     1      -1.370   1.542   2.633  1.00  0.00           H  
HETATM   44  H12 UNL     1      -2.996   0.549   2.257  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.967   2.185   1.057  1.00  0.00           H  
HETATM   46  H14 UNL     1      -3.380   1.564  -0.546  1.00  0.00           H  
HETATM   47  H15 UNL     1      -6.145   0.325  -1.664  1.00  0.00           H  
HETATM   48  H16 UNL     1      -6.836   1.519  -0.540  1.00  0.00           H  
HETATM   49  H17 UNL     1      -5.330   1.915  -1.428  1.00  0.00           H  
HETATM   50  H18 UNL     1      -5.380   0.664   2.363  1.00  0.00           H  
HETATM   51  H19 UNL     1      -6.423  -0.586   1.490  1.00  0.00           H  
HETATM   52  H20 UNL     1      -6.788   1.143   1.367  1.00  0.00           H  
HETATM   53  H21 UNL     1      -4.024  -0.767  -1.165  1.00  0.00           H  
HETATM   54  H22 UNL     1      -5.306  -1.630  -0.153  1.00  0.00           H  
HETATM   55  H23 UNL     1      -3.765  -1.099   2.853  1.00  0.00           H  
HETATM   56  H24 UNL     1      -3.154  -3.167   0.595  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.018  -4.258   0.269  1.00  0.00           H  
HETATM   58  H26 UNL     1       1.224  -0.673   1.391  1.00  0.00           H  
HETATM   59  H27 UNL     1       5.105  -1.995  -3.451  1.00  0.00           H  
HETATM   60  H28 UNL     1       3.810  -2.597  -2.412  1.00  0.00           H  
HETATM   61  H29 UNL     1       3.524  -1.261  -3.683  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   31
CONECT    4    5   36
CONECT    5    6    7    7
CONECT    6   37
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   27   38
CONECT   12   13   39   40
CONECT   13   14   15   27
CONECT   14   41   42   43
CONECT   15   16   21   44
CONECT   16   17   45   46
CONECT   17   18   19   20
CONECT   18   47   48   49
CONECT   19   50   51   52
CONECT   20   21   53   54
CONECT   21   22   23
CONECT   22   55
CONECT   23   24   24   56
CONECT   24   25   27
CONECT   25   26   26   57
CONECT   27   28
CONECT   28   58
CONECT   29   30   31   31
CONECT   30   59   60   61
CONECT   31   32
END

HMDB0031674
     RDKit          3D
Armillarinin
 61 64  0  0  0  0  0  0  0  0999 V2000
    8.1859    1.9799    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6987    1.0231   -0.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3643    0.6586   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    1.2570   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    0.9165   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285    1.5513    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6821   -0.0408   -1.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.4579   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.3418   -2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.0236   -0.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.3942   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6943   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656    0.4135    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    1.4817    1.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    0.2706    1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7748    1.2814    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.5208    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773    1.1086   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9208    0.4211    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5239   -0.8646   -0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5068   -1.0493    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089   -1.3932    2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.1883    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -2.0774    0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -3.2882    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6910   -3.2538    0.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573   -0.8153    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394   -0.8618    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351   -0.6425   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722   -1.6650   -2.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -0.2844   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0988   -1.0779   -2.9152 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1734    2.3634   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5224    2.8696    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129    1.4931    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7316    2.0111    0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    1.4033    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -1.1667   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195    0.4194   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053    1.6999   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    1.1559    1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148    2.4730    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697    1.5417    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.5490    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9666    2.1849    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796    1.5640   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1455    0.3253   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8361    1.5193   -0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300    1.9151   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    0.6641    2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -0.5856    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7876    1.1426    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236   -0.7666   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3057   -1.6296   -0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646   -1.0991    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539   -3.1674    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177   -4.2579    0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -0.6735    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1050   -1.9951   -3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100   -2.5972   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -1.2612   -3.6827 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  0
 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
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31  3  1  0
 27 11  1  0
 27 13  1  0
 21 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 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
 22 55  1  0
 23 56  1  0
 25 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₂₄H₂₉ClO₇

Average Molecular Weight

464.936

Monoisotopic Molecular Weight

464.160180989

IUPAC Name

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

Traditional Name

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

CAS Registry Number

127486-63-9

SMILES

COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1

InChI Identifier

InChI=1S/C24H29ClO7/c1-12-18(14(27)6-15(31-5)19(12)25)20(28)32-17-9-22(4)16-8-21(2,3)11-23(16,29)7-13(10-26)24(17,22)30/h6-7,10,16-17,27,29-30H,8-9,11H2,1-5H3

InChI Key

XOGUZUVXPLTDMB-UHFFFAOYSA-N

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-methoxybenzoic acid or derivatives
O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Methoxyphenol
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Anisole
Phenoxy compound
4-chlorophenol
M-cresol
4-halophenol
Methoxybenzene
Benzoyl
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Toluene
Phenol
Aryl chloride
Benzenoid
Aryl halide
Monocyclic benzene moiety
Tertiary alcohol
Vinylogous acid
Cyclic alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Organooxygen compound
Organohalogen compound
Organochloride
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031674)

Source

Endogenous

Endogenous (HMDB: HMDB0031674)

Plant

Plant (HMDB: HMDB0031674)

Animal

Animal (HMDB: HMDB0031674)

Exogenous

Food

Food (HMDB: HMDB0031674)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0031674)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031674)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031674)

Lipid metabolism pathway (HMDB: HMDB0031674)

Cellular process

Cell signaling (HMDB: HMDB0031674)

Biochemical process

Lipid transport (HMDB: HMDB0031674)

Role

Biological role

Energy source (HMDB: HMDB0031674)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031674)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0081 g/L	ALOGPS
logP	2.95	ALOGPS
logP	3.78	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.78 m³·mol⁻¹	ChemAxon
Polarizability	48.09 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	241.215	30932474
DeepCCS	[M+Na]+	216.64	30932474
AllCCS	[M+H]+	206.0	32859911
AllCCS	[M+H-H2O]+	204.2	32859911
AllCCS	[M+NH4]+	207.8	32859911
AllCCS	[M+Na]+	208.2	32859911
AllCCS	[M-H]-	208.7	32859911
AllCCS	[M+Na-2H]-	209.5	32859911
AllCCS	[M+HCOO]-	210.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Armillarinin	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1	4580.3	Standard polar	33892256
Armillarinin	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1	3151.9	Standard non polar	33892256
Armillarinin	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1	3314.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Armillarinin,1TMS,isomer #1	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C)C=C(C=O)C23O)C(C)=C1Cl	3516.3	Semi standard non polar	33892256
Armillarinin,1TMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O[Si](C)(C)C)C(C)=C1Cl	3522.8	Semi standard non polar	33892256
Armillarinin,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(C)=C1Cl	3556.3	Semi standard non polar	33892256
Armillarinin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C)C=C(C=O)C23O)C(C)=C1Cl	3449.3	Semi standard non polar	33892256
Armillarinin,2TMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C)C=C(C=O)C23O[Si](C)(C)C)C(C)=C1Cl	3434.5	Semi standard non polar	33892256
Armillarinin,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O[Si](C)(C)C)C(C)=C1Cl	3464.7	Semi standard non polar	33892256
Armillarinin,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C)C=C(C=O)C23O[Si](C)(C)C)C(C)=C1Cl	3419.2	Semi standard non polar	33892256
Armillarinin,1TBDMS,isomer #1	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C(C)(C)C)C=C(C=O)C23O)C(C)=C1Cl	3747.9	Semi standard non polar	33892256
Armillarinin,1TBDMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O[Si](C)(C)C(C)(C)C)C(C)=C1Cl	3767.5	Semi standard non polar	33892256
Armillarinin,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(C)=C1Cl	3782.8	Semi standard non polar	33892256
Armillarinin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C(C)(C)C)C=C(C=O)C23O)C(C)=C1Cl	3890.1	Semi standard non polar	33892256
Armillarinin,2TBDMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C(C)(C)C)C=C(C=O)C23O[Si](C)(C)C(C)(C)C)C(C)=C1Cl	3886.8	Semi standard non polar	33892256
Armillarinin,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O[Si](C)(C)C(C)(C)C)C(C)=C1Cl	3906.1	Semi standard non polar	33892256
Armillarinin,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O[Si](C)(C)C(C)(C)C)C=C(C=O)C23O[Si](C)(C)C(C)(C)C)C(C)=C1Cl	4044.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r6s-4970100000-7fa0d5bbf44e03a3f3af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarinin GC-MS (3 TMS) - 70eV, Positive	splash10-0gbi-5119004000-31eaebbf47bda85ee607	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 10V, Positive-QTOF	splash10-0002-0230900000-4c1dffdb423660ade888	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 20V, Positive-QTOF	splash10-0002-0890800000-fe9bf9ff0dd1ba932eb7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 40V, Positive-QTOF	splash10-00kb-1940000000-1783990c79fb3714fec6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 10V, Negative-QTOF	splash10-03di-0130900000-7057abd7ca59a4de7b1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 20V, Negative-QTOF	splash10-02ft-0770900000-2a4637e905c4b0674be1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 40V, Negative-QTOF	splash10-00di-0930000000-cc25308848cfaf1facfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 10V, Negative-QTOF	splash10-03di-0000900000-73f0f4f85a6e4466716b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 20V, Negative-QTOF	splash10-0229-0650900000-a3ea83f08ff53f768041	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 40V, Negative-QTOF	splash10-0a5a-9810300000-a664822af06e5386a345	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 10V, Positive-QTOF	splash10-014j-0260900000-551e1b69670bce2ced93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 20V, Positive-QTOF	splash10-0002-4950100000-367c85a04117fa5e02b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarinin 40V, Positive-QTOF	splash10-0002-9460000000-fa55c1d3fd20d0c1dc6d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008334

KNApSAcK ID

C00054382

Chemspider ID

19994085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21126387

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Armillarinin (HMDB0031674)

MOL for HMDB0031674 (Armillarinin)

3D MOL for HMDB0031674 (Armillarinin)

3D SDF for HMDB0031674 (Armillarinin)

3D-SDF for HMDB0031674 (Armillarinin)

PDB for HMDB0031674 (Armillarinin)

3D PDB for HMDB0031674 (Armillarinin)

SMILES for HMDB0031674 (Armillarinin)

INCHI for HMDB0031674 (Armillarinin)

Structure for HMDB0031674 (Armillarinin)

3D Structure for HMDB0031674 (Armillarinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra