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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:59 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037040

Secondary Accession Numbers

HMDB37040

Metabolite Identification

Common Name

Armillaric acid

Description

Armillaric acid, also known as armillarate, 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 Armillaric acid.

Structure

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


  Mrv0541 05061309312D          

 30 33  0  0  0  0            999 V2000
   -1.7788    2.8888    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
   -2.8261    1.9166    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
   -2.5079    0.5236    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
   -2.0218    2.1004    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
   -3.0691    1.1282    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
    2.6711    1.4877    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
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    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
   -0.6563    1.6795    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
   -3.8734    0.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 O   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
    0.5303   -0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.4679    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
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  1  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  9  1  0  0  0  0
 22  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 23 14  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26 19  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 17  1  0  0  0  0
 30 20  1  0  0  0  0
M  END

HMDB0037040
     RDKit          3D
Armillaric acid
 58 61  0  0  0  0  0  0  0  0999 V2000
    5.2082   -2.4115    1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980   -1.0662    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964   -0.5478    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8997    0.7040    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    1.2711   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8034    1.4375   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.9090   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094    1.7272   -0.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3008   -0.3476    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.9287    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -2.0854    0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -0.3574   -0.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.8600    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357   -0.9366   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750    0.2433   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    1.5245   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871    0.1011   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1592    1.3858   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5164    1.0261   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228    1.5836   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972    1.5450    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -0.4723   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1692   -0.9454   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -1.3070    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082   -0.9651    1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4050    2.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.0684    3.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -2.1636    3.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1428    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.0249    1.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2123   -2.8579    1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6268   -2.4120    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168   -3.0887    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5473   -1.1254    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546    0.7289    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101    2.4274   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6007   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -1.9033    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5655   -0.7171   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470   -1.8571   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    1.9713   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094    1.3307   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388    2.2619   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -0.1120   -2.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852    1.9514   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6637    2.0820   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.8511   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9474    2.5639   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2151    1.8070   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938    2.3877    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    0.7536    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541    1.8587    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -0.8269   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1321   -0.8521    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.8924   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461   -1.9252    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.7531    4.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    1.2746    1.7830 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  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
  9  2  1  0
 29 13  1  0
 29 15  1  0
 23 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 28 57  1  0
 30 58  1  0
M  END


  Mrv0541 05061309312D          

 30 33  0  0  0  0            999 V2000
   -1.7788    2.8888    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
   -2.8261    1.9166    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
   -2.5079    0.5236    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
   -2.0218    2.1004    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
   -3.0691    1.1282    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
    2.6711    1.4877    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
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    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
   -0.6563    1.6795    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
   -3.8734    0.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 O   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
    0.5303   -0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.4679    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
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  1  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  9  1  0  0  0  0
 22  4  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 23 14  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26 19  2  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 17  1  0  0  0  0
 30 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037040

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O

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

> <INCHI_KEY>
AOCKXACXCVTXBB-UHFFFAOYSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.4642

> <EXACT_MASS>
416.18350325

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.05938288109212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]indene-3-carboxylic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
4.2661454679999995

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.69755141755162

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.008610930267844

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8034171307519715

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
108.97219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]indene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037040
     RDKit          3D
Armillaric acid
 58 61  0  0  0  0  0  0  0  0999 V2000
    5.2082   -2.4115    1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980   -1.0662    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964   -0.5478    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8997    0.7040    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    1.2711   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8034    1.4375   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.9090   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094    1.7272   -0.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3008   -0.3476    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.9287    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -2.0854    0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -0.3574   -0.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.8600    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357   -0.9366   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750    0.2433   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    1.5245   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871    0.1011   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1592    1.3858   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5164    1.0261   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228    1.5836   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972    1.5450    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -0.4723   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1692   -0.9454   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -1.3070    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082   -0.9651    1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4050    2.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.0684    3.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -2.1636    3.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1428    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.0249    1.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2123   -2.8579    1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6268   -2.4120    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168   -3.0887    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5473   -1.1254    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546    0.7289    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101    2.4274   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6007   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -1.9033    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5655   -0.7171   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470   -1.8571   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    1.9713   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094    1.3307   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388    2.2619   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -0.1120   -2.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852    1.9514   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6637    2.0820   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.8511   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9474    2.5639   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2151    1.8070   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938    2.3877    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    0.7536    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541    1.8587    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -0.8269   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1321   -0.8521    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.8924   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461   -1.9252    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.7531    4.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    1.2746    1.7830 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  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
  9  2  1  0
 29 13  1  0
 29 15  1  0
 23 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 28 57  1  0
 30 58  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      -3.320   5.392   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      -5.275   3.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.774   3.921   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.729   2.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.726   2.792   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.225   3.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.230   1.763   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.132   0.192   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.990  -1.078   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.771   4.607   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.499   0.483   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   11                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   11   13                                                       
CONECT    6   12   14                                                       
CONECT    7   13   16                                                       
CONECT    8   12   21                                                       
CONECT    9   15   21                                                       
CONECT   10   17   22                                                       
CONECT   11    1    5   18                                                  
CONECT   12    6    8   15                                                  
CONECT   13    5    7   24                                                  
CONECT   14    6   19   23                                                  
CONECT   15    9   12   22                                                  
CONECT   16    7   18   25                                                  
CONECT   17   10   23   30                                                  
CONECT   18   11   16   20                                                  
CONECT   19   14   26   27                                                  
CONECT   20   18   28   30                                                  
CONECT   21    2    3    8    9                                             
CONECT   22    4   10   15   23                                             
CONECT   23   14   17   22   29                                             
CONECT   24   13                                                            
CONECT   25   16                                                            
CONECT   26   19                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   23                                                            
CONECT   30   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0037040
HETATM    1  C1  UNL     1       5.208  -2.411   1.154  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.398  -1.066   0.609  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.696  -0.548   0.529  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.900   0.704   0.025  1.00  0.00           C  
HETATM    5  O1  UNL     1       8.163   1.271  -0.080  1.00  0.00           O  
HETATM    6  C5  UNL     1       5.803   1.438  -0.400  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.506   0.909  -0.315  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.509   1.727  -0.765  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.301  -0.348   0.191  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.991  -0.929   0.295  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.773  -2.085   0.758  1.00  0.00           O  
HETATM   12  O4  UNL     1       1.793  -0.357  -0.073  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.549  -0.860   0.005  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.136  -0.937  -1.340  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.975   0.243  -0.878  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.287   1.525  -1.370  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.387   0.101  -1.312  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.159   1.386  -1.111  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.516   1.026  -0.609  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.623   1.584  -1.506  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.797   1.545   0.788  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.612  -0.472  -0.559  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.169  -0.945  -0.621  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.742  -1.307   0.705  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.608  -0.965   1.250  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.286  -1.405   2.633  1.00  0.00           C  
HETATM   27  O5  UNL     1      -0.210  -1.068   3.122  1.00  0.00           O  
HETATM   28  O6  UNL     1      -2.194  -2.164   3.305  1.00  0.00           O  
HETATM   29  C23 UNL     1      -0.634  -0.143   0.510  1.00  0.00           C  
HETATM   30  O7  UNL     1      -0.400   1.025   1.245  1.00  0.00           O  
HETATM   31  H1  UNL     1       6.212  -2.858   1.439  1.00  0.00           H  
HETATM   32  H2  UNL     1       4.627  -2.412   2.096  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.817  -3.089   0.371  1.00  0.00           H  
HETATM   34  H4  UNL     1       7.547  -1.125   0.862  1.00  0.00           H  
HETATM   35  H5  UNL     1       8.955   0.729   0.232  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.910   2.427  -0.805  1.00  0.00           H  
HETATM   37  H7  UNL     1       2.547   1.601  -0.813  1.00  0.00           H  
HETATM   38  H8  UNL     1       0.570  -1.903   0.447  1.00  0.00           H  
HETATM   39  H9  UNL     1       0.565  -0.717  -2.150  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.747  -1.857  -1.482  1.00  0.00           H  
HETATM   41  H11 UNL     1       0.184   1.971  -0.469  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.509   1.331  -2.087  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.039   2.262  -1.718  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.414  -0.112  -2.403  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.285   1.951  -2.071  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.664   2.082  -0.416  1.00  0.00           H  
HETATM   47  H17 UNL     1      -6.437   0.851  -1.582  1.00  0.00           H  
HETATM   48  H18 UNL     1      -5.947   2.564  -1.088  1.00  0.00           H  
HETATM   49  H19 UNL     1      -5.215   1.807  -2.514  1.00  0.00           H  
HETATM   50  H20 UNL     1      -4.094   2.388   1.004  1.00  0.00           H  
HETATM   51  H21 UNL     1      -4.544   0.754   1.528  1.00  0.00           H  
HETATM   52  H22 UNL     1      -5.854   1.859   0.918  1.00  0.00           H  
HETATM   53  H23 UNL     1      -5.181  -0.827  -1.451  1.00  0.00           H  
HETATM   54  H24 UNL     1      -5.132  -0.852   0.322  1.00  0.00           H  
HETATM   55  H25 UNL     1      -3.206  -1.892  -1.240  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.446  -1.925   1.294  1.00  0.00           H  
HETATM   57  H27 UNL     1      -1.907  -2.753   4.087  1.00  0.00           H  
HETATM   58  H28 UNL     1      -1.188   1.275   1.783  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3    9
CONECT    3    4   34
CONECT    4    5    6    6
CONECT    5   35
CONECT    6    7   36
CONECT    7    8    9    9
CONECT    8   37
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   29   38
CONECT   14   15   39   40
CONECT   15   16   17   29
CONECT   16   41   42   43
CONECT   17   18   23   44
CONECT   18   19   45   46
CONECT   19   20   21   22
CONECT   20   47   48   49
CONECT   21   50   51   52
CONECT   22   23   53   54
CONECT   23   24   55
CONECT   24   25   25   56
CONECT   25   26   29
CONECT   26   27   27   28
CONECT   28   57
CONECT   29   30
CONECT   30   58
END

HMDB0037040
     RDKit          3D
Armillaric acid
 58 61  0  0  0  0  0  0  0  0999 V2000
    5.2082   -2.4115    1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980   -1.0662    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964   -0.5478    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8997    0.7040    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631    1.2711   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8034    1.4375   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.9090   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094    1.7272   -0.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3008   -0.3476    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -0.9287    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -2.0854    0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -0.3574   -0.0730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493   -0.8600    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357   -0.9366   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750    0.2433   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871    1.5245   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871    0.1011   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1592    1.3858   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5164    1.0261   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228    1.5836   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972    1.5450    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -0.4723   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1692   -0.9454   -0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -1.3070    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082   -0.9651    1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2857   -1.4050    2.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.0684    3.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -2.1636    3.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.1428    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.0249    1.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2123   -2.8579    1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6268   -2.4120    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168   -3.0887    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5473   -1.1254    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9546    0.7289    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101    2.4274   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6007   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -1.9033    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5655   -0.7171   -2.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470   -1.8571   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    1.9713   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094    1.3307   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388    2.2619   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4143   -0.1120   -2.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852    1.9514   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6637    2.0820   -0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.8511   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9474    2.5639   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2151    1.8070   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938    2.3877    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5445    0.7536    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8541    1.8587    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1809   -0.8269   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1321   -0.8521    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063   -1.8924   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4461   -1.9252    1.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.7531    4.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    1.2746    1.7830 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  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
  9  2  1  0
 29 13  1  0
 29 15  1  0
 23 17  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 28 57  1  0
 30 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Armillarate	Generator
2-(2,4-Dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]indene-3-carboxylate	HMDB

Chemical Formula

C₂₃H₂₈O₇

Average Molecular Weight

416.4642

Monoisotopic Molecular Weight

416.18350325

IUPAC Name

2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]indene-3-carboxylic acid

Traditional Name

2-(2,4-dihydroxy-6-methylbenzoyloxy)-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]indene-3-carboxylic acid

CAS Registry Number

129251-06-5

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O

InChI Identifier

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

InChI Key

AOCKXACXCVTXBB-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-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
M-cresol
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0037040)
Cell membrane (HMDB: HMDB0037040)

Cellular substructure

Extracellular (HMDB: HMDB0037040)
Membrane (HMDB: HMDB0037040)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037040)

Source

Endogenous

Endogenous (HMDB: HMDB0037040)

Plant

Plant (HMDB: HMDB0037040)

Animal

Animal (HMDB: HMDB0037040)

Exogenous

Food

Food (HMDB: HMDB0037040)

Vegetable

Mushroom

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037040)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037040)

Cellular process

Cell signaling (HMDB: HMDB0037040)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037040)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037040)

Nutrient

Nutrient (HMDB: HMDB0037040)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037040)

Emulsifier (HMDB: HMDB0037040)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.26 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	0.097 g/L	ALOGPS
logP	3.22	ALOGPS
logP	4.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.97 m³·mol⁻¹	ChemAxon
Polarizability	44.06 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
DarkChem	[M+H]+	195.447	31661259
DarkChem	[M-H]-	190.086	31661259
DeepCCS	[M-2H]-	225.388	30932474
DeepCCS	[M+Na]+	200.616	30932474
AllCCS	[M+H]+	198.4	32859911
AllCCS	[M+H-H2O]+	196.2	32859911
AllCCS	[M+NH4]+	200.4	32859911
AllCCS	[M+Na]+	201.0	32859911
AllCCS	[M-H]-	199.8	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	200.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Armillaric acid	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O	4798.4	Standard polar	33892256
Armillaric acid	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O	3009.4	Standard non polar	33892256
Armillaric acid	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(O)=O)C12O	3305.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Armillaric acid,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3424.8	Semi standard non polar	33892256
Armillaric acid,1TMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3382.0	Semi standard non polar	33892256
Armillaric acid,1TMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O	3304.9	Semi standard non polar	33892256
Armillaric acid,1TMS,isomer #4	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C	3370.1	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3399.8	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O	3282.7	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C	3356.8	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O	3263.9	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #5	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C	3306.8	Semi standard non polar	33892256
Armillaric acid,2TMS,isomer #6	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C	3243.6	Semi standard non polar	33892256
Armillaric acid,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O	3283.5	Semi standard non polar	33892256
Armillaric acid,3TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C	3337.5	Semi standard non polar	33892256
Armillaric acid,3TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C	3240.8	Semi standard non polar	33892256
Armillaric acid,3TMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C	3234.0	Semi standard non polar	33892256
Armillaric acid,4TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C)C12O[Si](C)(C)C	3267.7	Semi standard non polar	33892256
Armillaric acid,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3663.5	Semi standard non polar	33892256
Armillaric acid,1TBDMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3605.4	Semi standard non polar	33892256
Armillaric acid,1TBDMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O	3525.9	Semi standard non polar	33892256
Armillaric acid,1TBDMS,isomer #4	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C	3595.0	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O	3859.0	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O	3722.4	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C	3831.5	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O	3687.2	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #5	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C	3760.8	Semi standard non polar	33892256
Armillaric acid,2TBDMS,isomer #6	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3702.7	Semi standard non polar	33892256
Armillaric acid,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O	3895.1	Semi standard non polar	33892256
Armillaric acid,3TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O)C12O[Si](C)(C)C(C)(C)C	3992.4	Semi standard non polar	33892256
Armillaric acid,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3887.4	Semi standard non polar	33892256
Armillaric acid,3TBDMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3853.6	Semi standard non polar	33892256
Armillaric acid,4TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C(=O)O[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	4051.5	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 - Armillaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kms-7892000000-89bab919b2280bd8f269	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillaric acid GC-MS (3 TMS) - 70eV, Positive	splash10-0006-0091000000-5146a188da3fdf8bd5a2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillaric acid 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 - Armillaric acid 10V, Positive-QTOF	splash10-014j-0567900000-f44950c76b357ed20bfb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 20V, Positive-QTOF	splash10-0uea-0955100000-88746aa04bec04fb68b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 40V, Positive-QTOF	splash10-0udi-3920000000-99bdcb1f526438196fd3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 10V, Negative-QTOF	splash10-01b9-0616900000-6441e0c9c692f1c0e8d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 20V, Negative-QTOF	splash10-00xr-0956200000-66ee22457931bbbe64ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 40V, Negative-QTOF	splash10-00di-1930000000-5c63fa662b6916c8ba53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 10V, Negative-QTOF	splash10-0udi-0109000000-4582574ae4b38a5a4cd0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 20V, Negative-QTOF	splash10-00di-0965000000-5ed4c9f099ee40027160	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 40V, Negative-QTOF	splash10-00di-4912000000-b3eaa0112ab9c04e35bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 10V, Positive-QTOF	splash10-00kb-0492600000-4e483b077750f45ff8bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 20V, Positive-QTOF	splash10-0uea-4954100000-d441c1375d1d17074219	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillaric acid 40V, Positive-QTOF	splash10-0zgs-6912000000-9e8abcdf16d0c83fafc5	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

FDB016022

KNApSAcK ID

C00021455

Chemspider ID

19343439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53461967

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1858881

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 Armillaric acid (HMDB0037040)

MOL for HMDB0037040 (Armillaric acid)

3D MOL for HMDB0037040 (Armillaric acid)

3D SDF for HMDB0037040 (Armillaric acid)

3D-SDF for HMDB0037040 (Armillaric acid)

PDB for HMDB0037040 (Armillaric acid)

3D PDB for HMDB0037040 (Armillaric acid)

SMILES for HMDB0037040 (Armillaric acid)

INCHI for HMDB0037040 (Armillaric acid)

Structure for HMDB0037040 (Armillaric acid)

3D Structure for HMDB0037040 (Armillaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra