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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:57:59 UTC

Update Date

2022-03-07 02:54:19 UTC

HMDB ID

HMDB0035027

Secondary Accession Numbers

HMDB35027

Metabolite Identification

Common Name

Melleolide F

Description

Melleolide F 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 significant number of articles have been published on Melleolide F.

Structure

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


  Mrv0541 05061308122D          

 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  1  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

HMDB0035027
     RDKit          3D
Melleolide F
 59 62  0  0  0  0  0  0  0  0999 V2000
    5.7400   -1.6975   -0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175   -0.2928   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6344    0.5137   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534    1.8300   -1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5794    2.5946   -1.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769    2.3333   -1.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935    1.5261   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    2.0118   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420    0.1962   -0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0602   -0.6141   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -1.8115   -0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.0886   -0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.9493   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517   -0.9549   -1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    0.0258   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    1.4526   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -0.3799   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    0.1899   -1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    0.2404   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    1.6594   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9321   -0.6962   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3999   -0.1174    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    0.0592    1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1948   -0.9531    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -1.0856    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394   -2.0765    2.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604   -2.7163    3.3853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -0.2377    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254    0.9316    1.2337 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -2.4168   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959   -1.8287    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8297   -1.8971   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6096    0.0821   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0377    3.1452   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    3.3678   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6674    2.9698   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -1.9613    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211   -1.9010   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422   -0.5028   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.5710   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    2.1749   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    1.6542   -1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -1.4951   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4180    1.1378   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -0.5417   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719    2.3232   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598    1.7846   -1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118    1.9292    0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.7540   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.4997   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -0.4479   -0.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -1.1089    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312    0.6364    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.0819    1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332   -1.5545    2.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -1.6103    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -2.8654    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -3.2996    2.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    0.9333    1.2101 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  1  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
 26 57  1  0
 27 58  1  0
 29 59  1  0
M  END


  Mrv0541 05061308122D          

 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  1  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>
HMDB0035027

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/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/h5-7,13,16,18,24-26,28H,8-11H2,1-4H3

> <INCHI_KEY>
PAOHIYZPMWDBLO-UHFFFAOYSA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.4807

> <EXACT_MASS>
402.204238692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
43.86025088146829

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2a-hydroxy-3-(hydroxymethyl)-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>
2.76

> <JCHEM_LOGP>
3.7936817123333317

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.55423122424302

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.69752185370273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7659305962148295

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
109.02969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035027
     RDKit          3D
Melleolide F
 59 62  0  0  0  0  0  0  0  0999 V2000
    5.7400   -1.6975   -0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175   -0.2928   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6344    0.5137   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534    1.8300   -1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5794    2.5946   -1.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769    2.3333   -1.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935    1.5261   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    2.0118   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420    0.1962   -0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0602   -0.6141   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -1.8115   -0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.0886   -0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.9493   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517   -0.9549   -1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    0.0258   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    1.4526   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -0.3799   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    0.1899   -1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    0.2404   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    1.6594   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9321   -0.6962   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3999   -0.1174    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    0.0592    1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1948   -0.9531    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -1.0856    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394   -2.0765    2.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604   -2.7163    3.3853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -0.2377    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254    0.9316    1.2337 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -2.4168   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959   -1.8287    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8297   -1.8971   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6096    0.0821   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0377    3.1452   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    3.3678   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6674    2.9698   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -1.9613    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211   -1.9010   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422   -0.5028   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.5710   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    2.1749   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    1.6542   -1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -1.4951   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4180    1.1378   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -0.5417   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719    2.3232   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598    1.7846   -1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118    1.9292    0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.7540   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.4997   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -0.4479   -0.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -1.1089    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312    0.6364    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.0819    1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332   -1.5545    2.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -1.6103    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -2.8654    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -3.2996    2.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    0.9333    1.2101 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  1  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
 26 57  1  0
 27 58  1  0
 29 59  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    HMDB0035027
HETATM    1  C1  UNL     1       5.740  -1.698  -0.058  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.517  -0.293  -0.472  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.634   0.514  -0.715  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.453   1.830  -1.102  1.00  0.00           C  
HETATM    5  O1  UNL     1       7.579   2.595  -1.333  1.00  0.00           O  
HETATM    6  C5  UNL     1       5.177   2.333  -1.245  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.093   1.526  -1.002  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.815   2.012  -1.139  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.242   0.196  -0.610  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.060  -0.614  -0.366  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.181  -1.812  -0.013  1.00  0.00           O  
HETATM   12  O4  UNL     1       1.789  -0.089  -0.515  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.671  -0.949  -0.256  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.352  -0.955  -1.346  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.182   0.026  -0.538  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.977   1.453  -1.012  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.569  -0.380  -0.264  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.627   0.190  -1.118  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.858   0.240  -0.226  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.385   1.659  -0.296  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.932  -0.696  -0.686  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.400  -0.117   1.167  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.914   0.059   1.169  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.195  -0.953   1.988  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.905  -1.086   1.707  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.039  -2.076   2.455  1.00  0.00           C  
HETATM   27  O5  UNL     1      -0.860  -2.716   3.385  1.00  0.00           O  
HETATM   28  C23 UNL     1      -0.307  -0.238   0.653  1.00  0.00           C  
HETATM   29  O6  UNL     1       0.225   0.932   1.234  1.00  0.00           O  
HETATM   30  H1  UNL     1       5.293  -2.417  -0.791  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.296  -1.829   0.968  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.830  -1.897  -0.025  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.610   0.082  -0.592  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.038   3.145  -0.606  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.083   3.368  -1.549  1.00  0.00           H  
HETATM   36  H7  UNL     1       2.667   2.970  -1.421  1.00  0.00           H  
HETATM   37  H8  UNL     1       0.959  -1.961   0.041  1.00  0.00           H  
HETATM   38  H9  UNL     1      -0.921  -1.901  -1.467  1.00  0.00           H  
HETATM   39  H10 UNL     1      -0.042  -0.503  -2.305  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.104   1.571  -1.195  1.00  0.00           H  
HETATM   41  H12 UNL     1      -1.282   2.175  -0.242  1.00  0.00           H  
HETATM   42  H13 UNL     1      -1.481   1.654  -1.980  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.633  -1.495  -0.316  1.00  0.00           H  
HETATM   44  H15 UNL     1      -3.418   1.138  -1.605  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.870  -0.542  -1.942  1.00  0.00           H  
HETATM   46  H17 UNL     1      -4.472   2.323  -0.312  1.00  0.00           H  
HETATM   47  H18 UNL     1      -5.860   1.785  -1.282  1.00  0.00           H  
HETATM   48  H19 UNL     1      -6.012   1.929   0.557  1.00  0.00           H  
HETATM   49  H20 UNL     1      -5.665  -1.754  -0.560  1.00  0.00           H  
HETATM   50  H21 UNL     1      -6.082  -0.500  -1.787  1.00  0.00           H  
HETATM   51  H22 UNL     1      -6.858  -0.448  -0.130  1.00  0.00           H  
HETATM   52  H23 UNL     1      -4.736  -1.109   1.490  1.00  0.00           H  
HETATM   53  H24 UNL     1      -4.831   0.636   1.858  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.595   1.082   1.361  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.633  -1.554   2.755  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.843  -1.610   2.888  1.00  0.00           H  
HETATM   57  H28 UNL     1       0.272  -2.865   1.724  1.00  0.00           H  
HETATM   58  H29 UNL     1      -1.478  -3.300   2.839  1.00  0.00           H  
HETATM   59  H30 UNL     1       1.198   0.933   1.210  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   56   57
CONECT   27   58
CONECT   28   29
CONECT   29   59
END

HMDB0035027
     RDKit          3D
Melleolide F
 59 62  0  0  0  0  0  0  0  0999 V2000
    5.7400   -1.6975   -0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175   -0.2928   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6344    0.5137   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4534    1.8300   -1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5794    2.5946   -1.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769    2.3333   -1.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935    1.5261   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    2.0118   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420    0.1962   -0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0602   -0.6141   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -1.8115   -0.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.0886   -0.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -0.9493   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517   -0.9549   -1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    0.0258   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    1.4526   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694   -0.3799   -0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    0.1899   -1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8578    0.2404   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    1.6594   -0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9321   -0.6962   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3999   -0.1174    1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    0.0592    1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1948   -0.9531    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -1.0856    1.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0394   -2.0765    2.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604   -2.7163    3.3853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -0.2377    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254    0.9316    1.2337 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2931   -2.4168   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959   -1.8287    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8297   -1.8971   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6096    0.0821   -0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0377    3.1452   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834    3.3678   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6674    2.9698   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -1.9613    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211   -1.9010   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422   -0.5028   -2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    1.5710   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    2.1749   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    1.6542   -1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -1.4951   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4180    1.1378   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -0.5417   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4719    2.3232   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598    1.7846   -1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0118    1.9292    0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647   -1.7540   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.4997   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8580   -0.4479   -0.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   -1.1089    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312    0.6364    1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.0819    1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332   -1.5545    2.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -1.6103    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -2.8654    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -3.2996    2.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    0.9333    1.2101 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  1  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
 26 57  1  0
 27 58  1  0
 29 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2a-Hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoic acid	HMDB

Chemical Formula

C₂₃H₃₀O₆

Average Molecular Weight

402.4807

Monoisotopic Molecular Weight

402.204238692

IUPAC Name

2a-hydroxy-3-(hydroxymethyl)-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

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

CAS Registry Number

117258-74-9

SMILES

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

InChI Identifier

InChI=1S/C23H30O6/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/h5-7,13,16,18,24-26,28H,8-11H2,1-4H3

InChI Key

PAOHIYZPMWDBLO-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
Resorcinol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
Toluene
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary alcohol
Cyclobutanol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035027)
Cell membrane (HMDB: HMDB0035027)

Cellular substructure

Extracellular (HMDB: HMDB0035027)
Membrane (HMDB: HMDB0035027)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035027)

Source

Endogenous

Endogenous (HMDB: HMDB0035027)

Plant

Plant (HMDB: HMDB0035027)

Animal

Animal (HMDB: HMDB0035027)

Exogenous

Food

Food (HMDB: HMDB0035027)

Vegetable

Mushroom

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035027)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035027)

Cellular process

Cell signaling (HMDB: HMDB0035027)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035027)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035027)

Nutrient

Nutrient (HMDB: HMDB0035027)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035027)

Emulsifier (HMDB: HMDB0035027)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.03 m³·mol⁻¹	ChemAxon
Polarizability	43.86 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]+	194.072	31661259
DarkChem	[M-H]-	188.279	31661259
DeepCCS	[M-2H]-	223.818	30932474
DeepCCS	[M+Na]+	199.029	30932474
AllCCS	[M+H]+	196.9	32859911
AllCCS	[M+H-H2O]+	194.6	32859911
AllCCS	[M+NH4]+	199.0	32859911
AllCCS	[M+Na]+	199.6	32859911
AllCCS	[M-H]-	198.0	32859911
AllCCS	[M+Na-2H]-	198.4	32859911
AllCCS	[M+HCOO]-	199.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melleolide F	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3886.8	Standard polar	33892256
Melleolide F	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3020.7	Standard non polar	33892256
Melleolide F	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3257.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melleolide F,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3323.3	Semi standard non polar	33892256
Melleolide F,1TMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3263.9	Semi standard non polar	33892256
Melleolide F,1TMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O	3204.6	Semi standard non polar	33892256
Melleolide F,1TMS,isomer #4	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C	3251.3	Semi standard non polar	33892256
Melleolide F,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(CO)C12O	3294.4	Semi standard non polar	33892256
Melleolide F,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O	3211.3	Semi standard non polar	33892256
Melleolide F,2TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C	3244.1	Semi standard non polar	33892256
Melleolide F,2TMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O	3185.8	Semi standard non polar	33892256
Melleolide F,2TMS,isomer #5	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C	3215.9	Semi standard non polar	33892256
Melleolide F,2TMS,isomer #6	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O[Si](C)(C)C	3192.7	Semi standard non polar	33892256
Melleolide F,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(CO[Si](C)(C)C)C12O	3217.7	Semi standard non polar	33892256
Melleolide F,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(CO)C12O[Si](C)(C)C	3248.2	Semi standard non polar	33892256
Melleolide F,3TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O[Si](C)(C)C	3199.9	Semi standard non polar	33892256
Melleolide F,3TMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C)C12O[Si](C)(C)C	3202.0	Semi standard non polar	33892256
Melleolide F,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(CO[Si](C)(C)C)C12O[Si](C)(C)C	3227.3	Semi standard non polar	33892256
Melleolide F,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3534.2	Semi standard non polar	33892256
Melleolide F,1TBDMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O	3463.6	Semi standard non polar	33892256
Melleolide F,1TBDMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O	3426.9	Semi standard non polar	33892256
Melleolide F,1TBDMS,isomer #4	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C(C)(C)C	3460.5	Semi standard non polar	33892256
Melleolide F,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(CO)C12O	3705.9	Semi standard non polar	33892256
Melleolide F,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O	3667.9	Semi standard non polar	33892256
Melleolide F,2TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C(C)(C)C	3681.2	Semi standard non polar	33892256
Melleolide F,2TBDMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O	3611.5	Semi standard non polar	33892256
Melleolide F,2TBDMS,isomer #5	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO)C12O[Si](C)(C)C(C)(C)C	3640.0	Semi standard non polar	33892256
Melleolide F,2TBDMS,isomer #6	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3655.5	Semi standard non polar	33892256
Melleolide F,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(CO[Si](C)(C)C(C)(C)C)C12O	3839.7	Semi standard non polar	33892256
Melleolide F,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(CO)C12O[Si](C)(C)C(C)(C)C	3873.2	Semi standard non polar	33892256
Melleolide F,3TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3853.1	Semi standard non polar	33892256
Melleolide F,3TBDMS,isomer #4	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(CO[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	3839.4	Semi standard non polar	33892256
Melleolide F,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(CO[Si](C)(C)C(C)(C)C)C12O[Si](C)(C)C(C)(C)C	4014.3	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 F GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-9670000000-7b84616adc5efd9d64a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melleolide F GC-MS (4 TMS) - 70eV, Positive	splash10-0udr-1009001000-a16bc492893106e8f35a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melleolide F 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 F 10V, Positive-QTOF	splash10-0udr-0569700000-01cc66fb75488d0d6799	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 20V, Positive-QTOF	splash10-0udr-0945100000-e0cf7b0164b05990f9ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 40V, Positive-QTOF	splash10-0udi-3931000000-7aff0394ec4d639d2416	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 10V, Negative-QTOF	splash10-0udi-0514900000-3118126a1091f1aae48c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 20V, Negative-QTOF	splash10-0fk9-0946200000-1b66c580560f5f4154e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 40V, Negative-QTOF	splash10-00di-1930000000-02c75e8cd19dc4c95dc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 10V, Positive-QTOF	splash10-0udr-0582900000-dac2c65c9f72e5b03938	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 20V, Positive-QTOF	splash10-0uei-5944200000-97f111d42759b4f78167	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 40V, Positive-QTOF	splash10-0ka9-5900000000-399b2c44a1dd93dc1446	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 10V, Negative-QTOF	splash10-0udi-0309700000-b0b0238c43ff23e5976c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 20V, Negative-QTOF	splash10-0fl0-1950200000-b12b8e4604ef578923fc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melleolide F 40V, Negative-QTOF	splash10-00xu-9721000000-1ebce1816270601fad14	2021-09-24	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

FDB013633

KNApSAcK ID

C00056548

Chemspider ID

35013816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14166118

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 F (HMDB0035027)

MOL for HMDB0035027 (Melleolide F)

3D MOL for HMDB0035027 (Melleolide F)

3D SDF for HMDB0035027 (Melleolide F)

3D-SDF for HMDB0035027 (Melleolide F)

PDB for HMDB0035027 (Melleolide F)

3D PDB for HMDB0035027 (Melleolide F)

SMILES for HMDB0035027 (Melleolide F)

INCHI for HMDB0035027 (Melleolide F)

Structure for HMDB0035027 (Melleolide F)

3D Structure for HMDB0035027 (Melleolide F)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra