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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:33:50 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254329

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Manoalide

Description

manoalide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. manoalide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Manoalide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Manoalide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1533004161503242D          

 30 32  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -8.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -9.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -8.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -7.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0255387
     RDKit          3D
2-Hydroxy-3-[(2R,6R)-6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)...
 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.8211    1.3256   -1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659    0.6334    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382    0.1198    0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649    0.0390    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    0.4902   -0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.3434   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674    1.4304   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7574    1.3003   -1.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0850    0.0954   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5271   -0.1109   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4940    0.6212   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964    0.0792   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9312    0.5042   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5478   -1.0318    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -1.2048    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -0.9926    2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980   -1.0112   -0.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -1.0051   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.7852   -1.7776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    0.5202    0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.2537   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237   -0.4257    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0666   -1.6650    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -2.8300   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4229   -2.0372    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3983   -0.9228    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9293    0.2118   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.6944    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525    1.9430   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405    1.0128    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    1.6078   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    2.3511   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    0.7706   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3193   -0.3640    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -1.0398    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9796    0.5821    1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340    1.4929   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.2079   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    2.3791   -1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.0440   -2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662    2.2155   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5820    0.2776    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4124    1.5070   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8225   -2.2108    0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4403   -0.3371    2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.5176    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2303   -2.5832   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2346   -0.0158    1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199    1.5267    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -1.2064   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109    0.2482   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180   -2.7783    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6727   -3.7744    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121   -2.8100   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2634   -2.4374    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -2.8973    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -0.6127    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3828   -1.2454    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6351    1.0656    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9226   -0.0909   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976    1.7419   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    2.7164    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1955    2.4700   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556    1.8496    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6541    1.3326    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207    0.0949    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 18  6  1  0
 28 22  1  0
 15 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 30 66  1  0
M  END

  Mrv1533004161503242D          

 30 32  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -8.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -9.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -8.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -7.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -7.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254329

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC1=C(C)CCCC1(C)C)=CCCC1=CCC(OC1O)C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3

> <INCHI_KEY>
FGJIDQWRRLDGDB-UHFFFAOYSA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.333076599933015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-4-{6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
4.9366320660000005

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.482109871728778

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.449862062678549

> <JCHEM_PKA_STRONGEST_BASIC>
-4.181379152188392

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
119.48259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
manoalide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255387
     RDKit          3D
2-Hydroxy-3-[(2R,6R)-6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)...
 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.8211    1.3256   -1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659    0.6334    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382    0.1198    0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649    0.0390    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    0.4902   -0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.3434   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674    1.4304   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7574    1.3003   -1.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0850    0.0954   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5271   -0.1109   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4940    0.6212   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964    0.0792   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9312    0.5042   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5478   -1.0318    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -1.2048    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -0.9926    2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980   -1.0112   -0.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -1.0051   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.7852   -1.7776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    0.5202    0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.2537   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237   -0.4257    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0666   -1.6650    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -2.8300   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4229   -2.0372    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3983   -0.9228    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9293    0.2118   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.6944    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525    1.9430   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405    1.0128    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    1.6078   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    2.3511   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    0.7706   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3193   -0.3640    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -1.0398    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9796    0.5821    1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340    1.4929   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.2079   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    2.3791   -1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.0440   -2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662    2.2155   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5820    0.2776    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4124    1.5070   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8225   -2.2108    0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4403   -0.3371    2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.5176    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2303   -2.5832   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2346   -0.0158    1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199    1.5267    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -1.2064   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109    0.2482   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180   -2.7783    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6727   -3.7744    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121   -2.8100   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2634   -2.4374    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -2.8973    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -0.6127    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3828   -1.2454    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6351    1.0656    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9226   -0.0909   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976    1.7419   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    2.7164    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1955    2.4700   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556    1.8496    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6541    1.3326    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207    0.0949    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 18  6  1  0
 28 22  1  0
 15 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 30 66  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.770 -16.230   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.675 -17.476   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.770 -16.230   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.711 -14.289   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0254329
HETATM    1  C1  UNL     1      -1.063  -1.357  -1.922  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.326   0.090  -1.973  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.445   1.006  -1.722  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.960   1.028  -1.338  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.570  -0.268  -1.005  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.042  -0.112  -0.658  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.629   1.046  -0.670  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.100   1.201  -0.324  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.431  -0.041   0.474  1.00  0.00           C  
HETATM   10  C10 UNL     1       6.854  -0.001   0.923  1.00  0.00           C  
HETATM   11  C11 UNL     1       7.211  -0.027   2.188  1.00  0.00           C  
HETATM   12  C12 UNL     1       8.659   0.026   2.281  1.00  0.00           C  
HETATM   13  O1  UNL     1       9.349   0.018   3.364  1.00  0.00           O  
HETATM   14  O2  UNL     1       9.133   0.084   0.999  1.00  0.00           O  
HETATM   15  C13 UNL     1       8.070   0.070   0.109  1.00  0.00           C  
HETATM   16  O3  UNL     1       8.054   1.322  -0.525  1.00  0.00           O  
HETATM   17  O4  UNL     1       5.162  -1.143  -0.326  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.781  -1.346  -0.307  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.462  -1.682   1.025  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.725   0.494  -2.335  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.823  -0.013  -1.546  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.143   0.166  -0.174  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.678   1.029   0.679  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.678   2.062   0.407  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.197   0.973   2.105  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.677   0.837   2.185  1.00  0.00           C  
HETATM   27  C22 UNL     1      -6.248   0.058   1.039  1.00  0.00           C  
HETATM   28  C23 UNL     1      -5.184  -0.787   0.400  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.611  -1.746   1.377  1.00  0.00           C  
HETATM   30  C25 UNL     1      -5.866  -1.576  -0.714  1.00  0.00           C  
HETATM   31  H1  UNL     1      -0.460  -1.598  -2.854  1.00  0.00           H  
HETATM   32  H2  UNL     1      -2.049  -1.941  -2.036  1.00  0.00           H  
HETATM   33  H3  UNL     1      -0.643  -1.760  -1.013  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.862   2.066  -1.845  1.00  0.00           H  
HETATM   35  H5  UNL     1       1.537   1.588  -2.136  1.00  0.00           H  
HETATM   36  H6  UNL     1       1.010   1.726  -0.425  1.00  0.00           H  
HETATM   37  H7  UNL     1       1.053  -0.668  -0.095  1.00  0.00           H  
HETATM   38  H8  UNL     1       1.475  -0.989  -1.807  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.118   1.950  -0.920  1.00  0.00           H  
HETATM   40  H10 UNL     1       5.219   2.127   0.251  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.668   1.267  -1.259  1.00  0.00           H  
HETATM   42  H12 UNL     1       4.768  -0.056   1.342  1.00  0.00           H  
HETATM   43  H13 UNL     1       6.518  -0.080   3.037  1.00  0.00           H  
HETATM   44  H14 UNL     1       8.135  -0.751  -0.644  1.00  0.00           H  
HETATM   45  H15 UNL     1       8.053   1.997   0.201  1.00  0.00           H  
HETATM   46  H16 UNL     1       3.458  -2.173  -0.946  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.886  -0.997   1.441  1.00  0.00           H  
HETATM   48  H18 UNL     1      -2.831   0.028  -3.395  1.00  0.00           H  
HETATM   49  H19 UNL     1      -2.767   1.578  -2.591  1.00  0.00           H  
HETATM   50  H20 UNL     1      -3.865  -1.165  -1.808  1.00  0.00           H  
HETATM   51  H21 UNL     1      -4.779   0.269  -2.195  1.00  0.00           H  
HETATM   52  H22 UNL     1      -1.691   1.686   0.707  1.00  0.00           H  
HETATM   53  H23 UNL     1      -2.888   2.912   1.149  1.00  0.00           H  
HETATM   54  H24 UNL     1      -2.743   2.570  -0.555  1.00  0.00           H  
HETATM   55  H25 UNL     1      -3.616   0.237   2.692  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.950   1.960   2.611  1.00  0.00           H  
HETATM   57  H27 UNL     1      -5.937   0.369   3.156  1.00  0.00           H  
HETATM   58  H28 UNL     1      -6.201   1.833   2.197  1.00  0.00           H  
HETATM   59  H29 UNL     1      -7.095  -0.533   1.425  1.00  0.00           H  
HETATM   60  H30 UNL     1      -6.684   0.751   0.280  1.00  0.00           H  
HETATM   61  H31 UNL     1      -3.493  -1.710   1.329  1.00  0.00           H  
HETATM   62  H32 UNL     1      -5.011  -1.666   2.409  1.00  0.00           H  
HETATM   63  H33 UNL     1      -4.883  -2.789   1.057  1.00  0.00           H  
HETATM   64  H34 UNL     1      -6.744  -2.074  -0.197  1.00  0.00           H  
HETATM   65  H35 UNL     1      -5.253  -2.436  -1.059  1.00  0.00           H  
HETATM   66  H36 UNL     1      -6.253  -0.936  -1.521  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    3   20
CONECT    3    4   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    7   18
CONECT    7    8   39
CONECT    8    9   40   41
CONECT    9   10   17   42
CONECT   10   11   11   15
CONECT   11   12   43
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   44
CONECT   16   45
CONECT   17   18
CONECT   18   19   46
CONECT   19   47
CONECT   20   21   48   49
CONECT   21   22   50   51
CONECT   22   23   23   28
CONECT   23   24   25
CONECT   24   52   53   54
CONECT   25   26   55   56
CONECT   26   27   57   58
CONECT   27   28   59   60
CONECT   28   29   30
CONECT   29   61   62   63
CONECT   30   64   65   66
END

HMDB0255387
     RDKit          3D
2-Hydroxy-3-[(2R,6R)-6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)...
 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.8211    1.3256   -1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659    0.6334    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382    0.1198    0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649    0.0390    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    0.4902   -0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.3434   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674    1.4304   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7574    1.3003   -1.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0850    0.0954   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5271   -0.1109   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4940    0.6212   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964    0.0792   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9312    0.5042   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5478   -1.0318    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -1.2048    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -0.9926    2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980   -1.0112   -0.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -1.0051   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -1.7852   -1.7776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    0.5202    0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.2537   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237   -0.4257    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0666   -1.6650    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434   -2.8300   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4229   -2.0372    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3983   -0.9228    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9293    0.2118   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.6944    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525    1.9430   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405    1.0128    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    1.6078   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025    2.3511   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    0.7706   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3193   -0.3640    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -1.0398    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9796    0.5821    1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340    1.4929   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.2079   -1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    2.3791   -1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.0440   -2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662    2.2155   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5820    0.2776    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4124    1.5070   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8225   -2.2108    0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4403   -0.3371    2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.5176    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2303   -2.5832   -1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2346   -0.0158    1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199    1.5267    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -1.2064   -0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109    0.2482   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180   -2.7783    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6727   -3.7744    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121   -2.8100   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2634   -2.4374    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -2.8973    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -0.6127    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3828   -1.2454    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6351    1.0656    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9226   -0.0909   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6976    1.7419   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    2.7164    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1955    2.4700   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556    1.8496    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6541    1.3326    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207    0.0949    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 18  6  1  0
 28 22  1  0
 15 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
 30 65  1  0
 30 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₅

Average Molecular Weight

416.558

Monoisotopic Molecular Weight

416.256274259

IUPAC Name

5-hydroxy-4-{6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydrofuran-2-one

Traditional Name

manoalide

CAS Registry Number

Not Available

SMILES

CC(CCC1=C(C)CCCC1(C)C)=CCCC1=CCC(OC1O)C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3

InChI Key

FGJIDQWRRLDGDB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
2-furanone
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	4.6	ALOGPS
logP	4.94	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.48 m³·mol⁻¹	ChemAxon
Polarizability	48.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	199.918	30932474
DeepCCS	[M-H]-	197.098	30932474
DeepCCS	[M-2H]-	232.442	30932474
DeepCCS	[M+Na]+	208.733	30932474
AllCCS	[M+H]+	208.0	32859911
AllCCS	[M+H-H2O]+	205.4	32859911
AllCCS	[M+NH4]+	210.3	32859911
AllCCS	[M+Na]+	211.0	32859911
AllCCS	[M-H]-	207.9	32859911
AllCCS	[M+Na-2H]-	209.6	32859911
AllCCS	[M+HCOO]-	211.7	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
manoalide,1TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3371.4	Semi standard non polar	33892256
manoalide,1TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3220.1	Standard non polar	33892256
manoalide,1TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3911.2	Standard polar	33892256
manoalide,1TMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	3411.2	Semi standard non polar	33892256
manoalide,1TMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	3229.0	Standard non polar	33892256
manoalide,1TMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	4003.0	Standard polar	33892256
manoalide,2TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3369.7	Semi standard non polar	33892256
manoalide,2TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3188.8	Standard non polar	33892256
manoalide,2TMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C)OC1O[Si](C)(C)C)CCC1=C(C)CCCC1(C)C	3677.0	Standard polar	33892256
manoalide,1TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	3594.6	Semi standard non polar	33892256
manoalide,1TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	3471.0	Standard non polar	33892256
manoalide,1TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	4021.8	Standard polar	33892256
manoalide,1TBDMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	3648.8	Semi standard non polar	33892256
manoalide,1TBDMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	3475.3	Standard non polar	33892256
manoalide,1TBDMS,isomer #2	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O)CCC1=C(C)CCCC1(C)C	4102.5	Standard polar	33892256
manoalide,2TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	3787.6	Semi standard non polar	33892256
manoalide,2TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	3612.7	Standard non polar	33892256
manoalide,2TBDMS,isomer #1	CC(=CCCC1=CCC(C2=CC(=O)OC2O[Si](C)(C)C(C)(C)C)OC1O[Si](C)(C)C(C)(C)C)CCC1=C(C)CCCC1(C)C	3831.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Manoalide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-0292100000-02c9bed97567b65558df	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Manoalide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Manoalide 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 - Manoalide 10V, Positive-QTOF	splash10-00or-0394400000-b63db15b612115e6487f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoalide 20V, Positive-QTOF	splash10-00vj-2459300000-b3cf22e7c43632e5b81c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoalide 40V, Positive-QTOF	splash10-014i-9562100000-14c5db16185c0c128dbc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoalide 10V, Negative-QTOF	splash10-014j-0105900000-9a2f8c5608bce0be465e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoalide 20V, Negative-QTOF	splash10-014i-1109600000-c5729c6df438ad1253c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoalide 40V, Negative-QTOF	splash10-0006-8449000000-21c2aa5161b53634ba5d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Manoalide

METLIN ID

Not Available

PubChem Compound

4009

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Manoalide (HMDB0254329)

MOL for HMDB0254329 (Manoalide)

3D MOL for HMDB0254329 (Manoalide)

3D SDF for HMDB0254329 (Manoalide)

3D-SDF for HMDB0254329 (Manoalide)

PDB for HMDB0254329 (Manoalide)

3D PDB for HMDB0254329 (Manoalide)

SMILES for HMDB0254329 (Manoalide)

INCHI for HMDB0254329 (Manoalide)

Structure for HMDB0254329 (Manoalide)

3D Structure for HMDB0254329 (Manoalide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra