Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:41:52 UTC

Update Date

2022-03-07 02:54:36 UTC

HMDB ID

HMDB0035689

Secondary Accession Numbers

HMDB35689

Metabolite Identification

Common Name

Melleolide

Description

Melleolide 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 Melleolide.

Structure

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


  Mrv0541 05061308382D          

 29 32  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 19  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 16  1  0  0  0  0
 23 14  1  0  0  0  0
 23 18  1  0  0  0  0
 23 22  1  0  0  0  0
 24 11  2  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 23  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
M  END

HMDB0035689
     RDKit          3D
Melleolide
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.7680   -0.3768   -1.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0802   -0.0479   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.3951   -1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652   -0.1149   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -0.4762   -1.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684    0.5313   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.9115    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.5483    1.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.6172    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.9799    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    1.5719    1.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.6832    0.3329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    1.0677    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    1.9490    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    1.1903    0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    1.9571    2.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    0.8514   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7294    0.3366    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.7519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058   -0.4345   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2009   -2.0927    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -0.8294   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713   -0.1864   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -1.2395   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5044   -1.0978    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -2.2100    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -2.1512    1.8988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.1138    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.2460    2.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -0.8863   -2.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1674   -1.0857   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630    0.5406   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1584   -0.9180   -2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0008   -1.3865   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    0.7623    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658    1.8999    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    1.5954    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2455    3.0078    0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.7588   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    1.5326    2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    3.0240    2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    2.0044    1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    1.7745   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -0.0824    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    1.1370    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    0.6393   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9308   -0.6838   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447   -1.0219   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954   -2.1846    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -2.1495    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704   -2.8964   -0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -0.2890   -2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.8854   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123    0.2338   -2.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -2.1756   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -3.1432    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -0.7810    2.6613 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
 25 28  1  0
 28 29  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 26 56  1  0
 29 57  1  0
M  END


  Mrv0541 05061308382D          

 29 32  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 19  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 16  1  0  0  0  0
 23 14  1  0  0  0  0
 23 18  1  0  0  0  0
 23 22  1  0  0  0  0
 24 11  2  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 20  2  0  0  0  0
 28 23  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035689

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O6/c1-12-5-15(25)7-17(26)19(12)20(27)29-18-10-22(4)16-9-21(2,3)8-13(16)6-14(11-24)23(18,22)28/h5-7,11,13,16,18,25-26,28H,8-10H2,1-4H3

> <INCHI_KEY>
SJZRUQOYQZRISL-UHFFFAOYSA-N

> <FORMULA>
C23H28O6

> <MOLECULAR_WEIGHT>
400.4648

> <EXACT_MASS>
400.188588628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
43.06506164059985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
4.107529215666666

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.553558546998199

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697502462221147

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7622191427378207

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
108.04679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035689
     RDKit          3D
Melleolide
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.7680   -0.3768   -1.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0802   -0.0479   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.3951   -1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652   -0.1149   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -0.4762   -1.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684    0.5313   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.9115    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.5483    1.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.6172    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.9799    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    1.5719    1.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.6832    0.3329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    1.0677    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    1.9490    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    1.1903    0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    1.9571    2.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    0.8514   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7294    0.3366    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.7519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058   -0.4345   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2009   -2.0927    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -0.8294   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713   -0.1864   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -1.2395   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5044   -1.0978    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -2.2100    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -2.1512    1.8988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.1138    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.2460    2.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -0.8863   -2.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1674   -1.0857   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630    0.5406   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1584   -0.9180   -2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0008   -1.3865   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    0.7623    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658    1.8999    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    1.5954    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2455    3.0078    0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.7588   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    1.5326    2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    3.0240    2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    2.0044    1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    1.7745   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -0.0824    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    1.1370    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    0.6393   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9308   -0.6838   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447   -1.0219   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954   -2.1846    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -2.1495    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704   -2.8964   -0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -0.2890   -2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.8854   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123    0.2338   -2.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -2.1756   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -3.1432    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -0.7810    2.6613 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
 25 28  1  0
 28 29  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 26 56  1  0
 29 57  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      -2.726   2.792   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.681   0.977   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      -4.087  -1.623   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       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.706   1.416   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      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.631   0.535   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       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.538  -2.409   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.499   0.483   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   12   15                                                       
CONECT    6   13   14                                                       
CONECT    7   15   17                                                       
CONECT    8   13   21                                                       
CONECT    9   16   21                                                       
CONECT   10   18   22                                                       
CONECT   11   14   24                                                       
CONECT   12    1    5   19                                                  
CONECT   13    6    8   16                                                  
CONECT   14    6   11   23                                                  
CONECT   15    5    7   25                                                  
CONECT   16    9   13   22                                                  
CONECT   17    7   19   26                                                  
CONECT   18   10   23   29                                                  
CONECT   19   12   17   20                                                  
CONECT   20   19   27   29                                                  
CONECT   21    2    3    8    9                                             
CONECT   22    4   10   16   23                                             
CONECT   23   14   18   22   28                                             
CONECT   24   11                                                            
CONECT   25   15                                                            
CONECT   26   17                                                            
CONECT   27   20                                                            
CONECT   28   23                                                            
CONECT   29   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0035689
HETATM    1  C1  UNL     1       2.768  -0.377  -1.664  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.080  -0.048  -1.086  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.230  -0.395  -1.762  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.465  -0.115  -1.280  1.00  0.00           C  
HETATM    5  O1  UNL     1       7.617  -0.476  -1.982  1.00  0.00           O  
HETATM    6  C5  UNL     1       6.568   0.531  -0.087  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.435   0.911   0.650  1.00  0.00           C  
HETATM    8  O2  UNL     1       5.674   1.548   1.821  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.211   0.617   0.141  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.997   0.980   0.843  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.011   1.572   1.931  1.00  0.00           O  
HETATM   12  O4  UNL     1       1.725   0.683   0.333  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.611   1.068   1.067  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.297   1.949   0.216  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.455   1.190   0.829  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.003   1.957   2.012  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.493   0.851  -0.183  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.729   0.337   0.473  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.264  -0.752  -0.430  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.706  -0.435  -0.792  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.201  -2.093   0.288  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.386  -0.829  -1.637  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.071  -0.186  -1.174  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.206  -1.240  -0.665  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.504  -1.098   0.422  1.00  0.00           C  
HETATM   26  C22 UNL     1       0.335  -2.210   0.855  1.00  0.00           C  
HETATM   27  O5  UNL     1       1.045  -2.151   1.899  1.00  0.00           O  
HETATM   28  C23 UNL     1      -0.531   0.114   1.209  1.00  0.00           C  
HETATM   29  O6  UNL     1      -0.669  -0.246   2.578  1.00  0.00           O  
HETATM   30  H1  UNL     1       2.934  -0.886  -2.647  1.00  0.00           H  
HETATM   31  H2  UNL     1       2.167  -1.086  -1.076  1.00  0.00           H  
HETATM   32  H3  UNL     1       2.163   0.541  -1.920  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.158  -0.918  -2.727  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.001  -1.386  -1.780  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.544   0.762   0.312  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.066   1.900   2.490  1.00  0.00           H  
HETATM   37  H8  UNL     1       0.821   1.595   2.021  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.245   3.008   0.489  1.00  0.00           H  
HETATM   39  H10 UNL     1      -0.167   1.759  -0.870  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.668   1.533   2.979  1.00  0.00           H  
HETATM   41  H12 UNL     1      -1.655   3.024   2.010  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.111   2.004   1.936  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.742   1.774  -0.747  1.00  0.00           H  
HETATM   44  H15 UNL     1      -3.549  -0.082   1.476  1.00  0.00           H  
HETATM   45  H16 UNL     1      -4.510   1.137   0.615  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.858   0.639  -0.637  1.00  0.00           H  
HETATM   47  H18 UNL     1      -5.931  -0.684  -1.853  1.00  0.00           H  
HETATM   48  H19 UNL     1      -6.345  -1.022  -0.100  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.995  -2.185   1.052  1.00  0.00           H  
HETATM   50  H21 UNL     1      -3.209  -2.149   0.782  1.00  0.00           H  
HETATM   51  H22 UNL     1      -4.270  -2.896  -0.483  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.810  -0.289  -2.488  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.168  -1.885  -1.899  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.612   0.234  -2.096  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.166  -2.176  -1.243  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.392  -3.143   0.304  1.00  0.00           H  
HETATM   57  H28 UNL     1      -1.493  -0.781   2.661  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    9
CONECT    3    4   33
CONECT    4    5    6    6
CONECT    5   34
CONECT    6    7   35
CONECT    7    8    9    9
CONECT    8   36
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   28   37
CONECT   14   15   38   39
CONECT   15   16   17   28
CONECT   16   40   41   42
CONECT   17   18   23   43
CONECT   18   19   44   45
CONECT   19   20   21   22
CONECT   20   46   47   48
CONECT   21   49   50   51
CONECT   22   23   52   53
CONECT   23   24   54
CONECT   24   25   25   55
CONECT   25   26   28
CONECT   26   27   27   56
CONECT   28   29
CONECT   29   57
END

HMDB0035689
     RDKit          3D
Melleolide
 57 60  0  0  0  0  0  0  0  0999 V2000
    2.7680   -0.3768   -1.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0802   -0.0479   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.3951   -1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652   -0.1149   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -0.4762   -1.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684    0.5313   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4354    0.9115    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    1.5483    1.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2112    0.6172    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967    0.9799    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    1.5719    1.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250    0.6832    0.3329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6107    1.0677    1.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    1.9490    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550    1.1903    0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    1.9571    2.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    0.8514   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7294    0.3366    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.7519   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058   -0.4345   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2009   -2.0927    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858   -0.8294   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713   -0.1864   -1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -1.2395   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5044   -1.0978    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -2.2100    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -2.1512    1.8988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5307    0.1138    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -0.2460    2.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -0.8863   -2.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1674   -1.0857   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630    0.5406   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1584   -0.9180   -2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0008   -1.3865   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    0.7623    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658    1.8999    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    1.5954    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2455    3.0078    0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.7588   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    1.5326    2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    3.0240    2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    2.0044    1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    1.7745   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -0.0824    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5104    1.1370    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    0.6393   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9308   -0.6838   -1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447   -1.0219   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954   -2.1846    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -2.1495    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704   -2.8964   -0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8099   -0.2890   -2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.8854   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123    0.2338   -2.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -2.1756   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -3.1432    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935   -0.7810    2.6613 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
 25 28  1  0
 28 29  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 26 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₂₃H₂₈O₆

Average Molecular Weight

400.4648

Monoisotopic Molecular Weight

400.188588628

IUPAC Name

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

Traditional Name

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

CAS Registry Number

82869-08-7

SMILES

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

InChI Identifier

InChI=1S/C23H28O6/c1-12-5-15(25)7-17(26)19(12)20(27)29-18-10-22(4)16-9-21(2,3)8-13(16)6-14(11-24)23(18,22)28/h5-7,11,13,16,18,25-26,28H,8-10H2,1-4H3

InChI Key

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035689)

Source

Endogenous

Endogenous (HMDB: HMDB0035689)

Plant

Plant (HMDB: HMDB0035689)

Animal

Animal (HMDB: HMDB0035689)

Exogenous

Food

Food (HMDB: HMDB0035689)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0035689)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035689)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035689)

Lipid metabolism pathway (HMDB: HMDB0035689)

Cellular process

Cell signaling (HMDB: HMDB0035689)

Biochemical process

Lipid transport (HMDB: HMDB0035689)

Role

Biological role

Energy source (HMDB: HMDB0035689)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035689)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.33	ALOGPS
logP	4.11	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.05 m³·mol⁻¹	ChemAxon
Polarizability	43.07 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]+	190.271	31661259
DarkChem	[M-H]-	186.247	31661259
DeepCCS	[M-2H]-	223.708	30932474
DeepCCS	[M+Na]+	198.936	30932474
AllCCS	[M+H]+	196.5	32859911
AllCCS	[M+H-H2O]+	194.2	32859911
AllCCS	[M+NH4]+	198.6	32859911
AllCCS	[M+Na]+	199.2	32859911
AllCCS	[M-H]-	197.8	32859911
AllCCS	[M+Na-2H]-	198.1	32859911
AllCCS	[M+HCOO]-	198.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.23 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8376 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2490.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	219.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	809.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	753.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1056.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	480.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1721.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	217.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	154.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	35.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melleolide	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O	4456.7	Standard polar	33892256
Melleolide	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O	2935.1	Standard non polar	33892256
Melleolide	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O	3175.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melleolide,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O	3284.7	Semi standard non polar	33892256
Melleolide,1TMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O	3233.5	Semi standard non polar	33892256
Melleolide,1TMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O[Si](C)(C)C	3241.2	Semi standard non polar	33892256
Melleolide,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)C12O	3265.3	Semi standard non polar	33892256
Melleolide,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O[Si](C)(C)C	3251.4	Semi standard non polar	33892256
Melleolide,2TMS,isomer #3	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O[Si](C)(C)C	3219.2	Semi standard non polar	33892256
Melleolide,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)C12O[Si](C)(C)C	3263.6	Semi standard non polar	33892256
Melleolide,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)C12O	3511.1	Semi standard non polar	33892256
Melleolide,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)C12O	3451.4	Semi standard non polar	33892256
Melleolide,1TBDMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O[Si](C)(C)C(C)(C)C	3477.8	Semi standard non polar	33892256
Melleolide,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)C12O	3691.0	Semi standard non polar	33892256
Melleolide,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)C12O[Si](C)(C)C(C)(C)C	3694.1	Semi standard non polar	33892256
Melleolide,2TBDMS,isomer #3	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12O[Si](C)(C)C(C)(C)C	3650.7	Semi standard non polar	33892256
Melleolide,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)C12O[Si](C)(C)C(C)(C)C	3849.8	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 - Melleolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pba-3891000000-ac928b496425dc787d37	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melleolide GC-MS (3 TMS) - 70eV, Positive	splash10-004i-1090001000-13db372d9747bf0eef94	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melleolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melleolide 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 - Melleolide 10V, Positive-QTOF	splash10-0udi-0554900000-99650a5e5fc100689a53	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 20V, Positive-QTOF	splash10-0ue9-1942100000-49cbdab2b3d93e37cd9f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 40V, Positive-QTOF	splash10-0ue9-3920000000-5c7ae6ea7657ac251289	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 10V, Negative-QTOF	splash10-0002-0419000000-2a642c5acb73e4c7294f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 20V, Negative-QTOF	splash10-006t-0956000000-6f17322662173d60037e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 40V, Negative-QTOF	splash10-00di-2930000000-16f17e499fe4fb6a1f24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 10V, Positive-QTOF	splash10-0ue9-0592800000-54d8ebff9c2ef069e5d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 20V, Positive-QTOF	splash10-0ue9-5944100000-e6417d665ebd6061ba7a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 40V, Positive-QTOF	splash10-0zg0-4911000000-f9e11f2b4b9b2e74a357	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 10V, Negative-QTOF	splash10-0002-0209000000-0ec93e71adcb7044bb48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 20V, Negative-QTOF	splash10-00dj-1954000000-bfc5406abf40a051b3da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide 40V, Negative-QTOF	splash10-00di-6912000000-9e4d975d3a4b7402cd04	2021-09-23	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

FDB014406

KNApSAcK ID

C00021452

Chemspider ID

385066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

435402

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Melleolide (HMDB0035689)

MOL for HMDB0035689 (Melleolide)

3D MOL for HMDB0035689 (Melleolide)

3D SDF for HMDB0035689 (Melleolide)

3D-SDF for HMDB0035689 (Melleolide)

PDB for HMDB0035689 (Melleolide)

3D PDB for HMDB0035689 (Melleolide)

SMILES for HMDB0035689 (Melleolide)

INCHI for HMDB0035689 (Melleolide)

Structure for HMDB0035689 (Melleolide)

3D Structure for HMDB0035689 (Melleolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra