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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:40:36 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036524

Secondary Accession Numbers

HMDB36524

Metabolite Identification

Common Name

3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide

Description

3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide.

Structure

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

  Mrv0541 05061309112D          

 28 30  0  0  0  0            999 V2000
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    5.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1839    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    3.6960    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 18  4  1  0  0  0  0
 18 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 16  1  0  0  0  0
 28 20  1  0  0  0  0
M  END

HMDB0036524
     RDKit          3D
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen...
 57 59  0  0  0  0  0  0  0  0999 V2000
    1.0443   -2.9750    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -2.7138    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492   -1.6011   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901   -0.2013    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    0.0231    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468    0.3466    1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.4583    2.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962    0.5774    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    1.4632   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674    1.1595    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7460    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052   -0.4190    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.6604    2.2518 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593    0.8345   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    1.8226   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671    0.4374   -1.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142    0.8304   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.9051   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.2533    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    0.2433    1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.7467    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700    2.2836    1.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046   -1.0033   -2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.9635   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892   -2.0218   -0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -3.2582   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189   -3.8185   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -5.0331   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.9470    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -4.0283    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -2.2597    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -0.1048    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.6864   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    2.4386   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    0.8968   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.4771    2.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -1.3376   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6402   -0.0972   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8924    0.3216    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -1.3611    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208    1.4083   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    1.8740   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    2.8103   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    0.9801   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553    0.0604   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.7816   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7832    0.0097   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9210    1.7136   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489    2.1452    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    0.5400    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    2.6596   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.5902    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    2.6876    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    3.1962    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -1.1499   -2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411   -1.1902   -2.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -2.7714   -0.6869 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27  2  1  0
 24  3  1  0
 21 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 25 57  1  0
M  END

  Mrv0541 05061309112D          

 28 30  0  0  0  0            999 V2000
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    5.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1839    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    3.6960    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 18  4  1  0  0  0  0
 18 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 16  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036524

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H29ClO7/c1-9-14-15(27-17(24)19(5,25)11(3)21)18(4)10(2)13(22)7-6-12(18)8-20(14,26)28-16(9)23/h10-13,15,22,25-26H,6-8H2,1-5H3

> <INCHI_KEY>
IYBZGGXFPLMHRX-UHFFFAOYSA-N

> <FORMULA>
C20H29ClO7

> <MOLECULAR_WEIGHT>
416.893

> <EXACT_MASS>
416.160180989

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.609180284616436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
2.2295938630000007

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.79195469006081

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.061968232601705

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8264845630611557

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
100.75489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036524
     RDKit          3D
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen...
 57 59  0  0  0  0  0  0  0  0999 V2000
    1.0443   -2.9750    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -2.7138    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492   -1.6011   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901   -0.2013    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    0.0231    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468    0.3466    1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.4583    2.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962    0.5774    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    1.4632   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674    1.1595    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7460    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052   -0.4190    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.6604    2.2518 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593    0.8345   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    1.8226   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671    0.4374   -1.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142    0.8304   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.9051   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.2533    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    0.2433    1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.7467    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700    2.2836    1.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046   -1.0033   -2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.9635   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892   -2.0218   -0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -3.2582   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189   -3.8185   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -5.0331   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.9470    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -4.0283    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -2.2597    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -0.1048    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.6864   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    2.4386   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    0.8968   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.4771    2.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -1.3376   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6402   -0.0972   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8924    0.3216    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -1.3611    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208    1.4083   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    1.8740   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    2.8103   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    0.9801   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553    0.0604   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.7816   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7832    0.0097   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9210    1.7136   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489    2.1452    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    0.5400    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    2.6596   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.5902    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    2.6876    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    3.1962    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -1.1499   -2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411   -1.1902   -2.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -2.7714   -0.6869 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27  2  1  0
 24  3  1  0
 21 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.507   9.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864   5.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.343   8.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.737   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       3.507   6.899   0.000  0.00  0.00          Cl+0
HETATM   22  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.137   5.923   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.197   9.773   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.036   0.541   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8   12   20                                                       
CONECT    9    1   14   16                                                  
CONECT   10    2   13   18                                                  
CONECT   11    3   19   21                                                  
CONECT   12    6    8   18                                                  
CONECT   13    7   10   22                                                  
CONECT   14    9   15   20                                                  
CONECT   15   14   18   27                                                  
CONECT   16    9   23   28                                                  
CONECT   17   19   24   27                                                  
CONECT   18    4   10   12   15                                             
CONECT   19    5   11   17   25                                             
CONECT   20    8   14   26   28                                             
CONECT   21   11                                                            
CONECT   22   13                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   15   17                                                       
CONECT   28   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0036524
HETATM    1  C1  UNL     1       1.044  -2.975   1.085  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.076  -2.714   0.131  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.649  -1.601  -0.231  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.390  -0.201   0.160  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.012   0.023   0.090  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.847   0.347   1.113  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.369   0.458   2.267  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.296   0.577   0.900  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.615   1.463  -0.266  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.867   1.159   2.059  1.00  0.00           O  
HETATM   11  C8  UNL     1       4.043  -0.746   0.720  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.505  -0.419   0.473  1.00  0.00           C  
HETATM   13 CL1  UNL     1       3.986  -1.660   2.252  1.00  0.00          CL  
HETATM   14  C10 UNL     1      -1.159   0.834  -0.605  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.063   1.823  -1.107  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.967   0.437  -1.761  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.414   0.830  -1.770  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.125   0.905  -0.484  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.304   1.253   0.707  1.00  0.00           C  
HETATM   20  O4  UNL     1      -3.327   0.243   1.628  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.951   1.747   0.305  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.170   2.284   1.463  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.805  -1.003  -2.222  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.784  -1.963  -1.096  1.00  0.00           C  
HETATM   25  O5  UNL     1      -2.989  -2.022  -0.390  1.00  0.00           O  
HETATM   26  O6  UNL     1      -1.535  -3.258  -1.528  1.00  0.00           O  
HETATM   27  C20 UNL     1      -0.619  -3.818  -0.675  1.00  0.00           C  
HETATM   28  O7  UNL     1      -0.313  -5.033  -0.606  1.00  0.00           O  
HETATM   29  H1  UNL     1       1.967  -2.947   0.482  1.00  0.00           H  
HETATM   30  H2  UNL     1       0.953  -4.028   1.437  1.00  0.00           H  
HETATM   31  H3  UNL     1       1.002  -2.260   1.920  1.00  0.00           H  
HETATM   32  H4  UNL     1      -0.639  -0.105   1.235  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.696   1.686  -0.271  1.00  0.00           H  
HETATM   34  H6  UNL     1       3.095   2.439  -0.216  1.00  0.00           H  
HETATM   35  H7  UNL     1       3.313   0.897  -1.192  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.176   1.477   2.679  1.00  0.00           H  
HETATM   37  H9  UNL     1       3.641  -1.338  -0.092  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.640  -0.097  -0.575  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.892   0.322   1.194  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.115  -1.361   0.592  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.221   1.408  -2.117  1.00  0.00           H  
HETATM   42  H14 UNL     1       0.771   1.874  -0.422  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.508   2.810  -1.318  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.558   0.980  -2.680  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.955   0.060  -2.401  1.00  0.00           H  
HETATM   46  H18 UNL     1      -3.602   1.782  -2.358  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.783   0.010  -0.260  1.00  0.00           H  
HETATM   48  H20 UNL     1      -4.921   1.714  -0.579  1.00  0.00           H  
HETATM   49  H21 UNL     1      -3.749   2.145   1.259  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.409   0.540   2.573  1.00  0.00           H  
HETATM   51  H23 UNL     1      -2.173   2.660  -0.338  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.118   1.590   2.317  1.00  0.00           H  
HETATM   53  H25 UNL     1      -0.202   2.688   1.132  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.742   3.196   1.813  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.872  -1.150  -2.812  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.641  -1.190  -2.927  1.00  0.00           H  
HETATM   57  H29 UNL     1      -3.556  -2.771  -0.687  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   27
CONECT    3    4   24
CONECT    4    5   14   32
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   11
CONECT    9   33   34   35
CONECT   10   36
CONECT   11   12   13   37
CONECT   12   38   39   40
CONECT   14   15   16   21
CONECT   15   41   42   43
CONECT   16   17   23   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   21   49
CONECT   20   50
CONECT   21   22   51
CONECT   22   52   53   54
CONECT   23   24   55   56
CONECT   24   25   26
CONECT   25   57
CONECT   26   27
CONECT   27   28   28
END

HMDB0036524
     RDKit          3D
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen...
 57 59  0  0  0  0  0  0  0  0999 V2000
    1.0443   -2.9750    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -2.7138    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492   -1.6011   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901   -0.2013    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    0.0231    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468    0.3466    1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.4583    2.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962    0.5774    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    1.4632   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674    1.1595    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.7460    0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052   -0.4190    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -1.6604    2.2518 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593    0.8345   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    1.8226   -1.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671    0.4374   -1.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142    0.8304   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1247    0.9051   -0.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.2533    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    0.2433    1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.7467    0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700    2.2836    1.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046   -1.0033   -2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.9635   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892   -2.0218   -0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -3.2582   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189   -3.8185   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -5.0331   -0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.9470    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -4.0283    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -2.2597    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -0.1048    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.6864   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    2.4386   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    0.8968   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760    1.4771    2.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -1.3376   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6402   -0.0972   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8924    0.3216    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -1.3611    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208    1.4083   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    1.8740   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    2.8103   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578    0.9801   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553    0.0604   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    1.7816   -2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7832    0.0097   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9210    1.7136   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489    2.1452    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    0.5400    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    2.6596   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.5902    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2019    2.6876    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421    3.1962    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -1.1499   -2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411   -1.1902   -2.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -2.7714   -0.6869 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
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
  4 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27  2  1  0
 24  3  1  0
 21 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,9a-Dihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoic acid	HMDB

Chemical Formula

C₂₀H₂₉ClO₇

Average Molecular Weight

416.893

Monoisotopic Molecular Weight

416.160180989

IUPAC Name

6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate

Traditional Name

6,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-chloro-2-hydroxy-2-methylbutanoate

CAS Registry Number

264607-21-8

SMILES

CC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C

InChI Identifier

InChI=1S/C20H29ClO7/c1-9-14-15(27-17(24)19(5,25)11(3)21)18(4)10(2)13(22)7-6-12(18)8-20(14,26)28-16(9)23/h10-13,15,22,25-26H,6-8H2,1-5H3

InChI Key

IYBZGGXFPLMHRX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Alcohol
Alkyl halide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organohalogen compound
Organochloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036524)

Source

Endogenous

Endogenous (HMDB: HMDB0036524)

Animal

Animal (HMDB: HMDB0036524)

Exogenous

Food

Food (HMDB: HMDB0036524)

Exogenous (HMDB: HMDB0036524)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036524)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036524)

Lipid metabolism pathway (HMDB: HMDB0036524)

Cellular process

Cell signaling (HMDB: HMDB0036524)

Biochemical process

Lipid transport (HMDB: HMDB0036524)

Role

Biological role

Energy source (HMDB: HMDB0036524)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036524)

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	0.38 g/L	ALOGPS
logP	1.37	ALOGPS
logP	2.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.06	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	41.61 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	221.208	30932474
DeepCCS	[M+Na]+	196.312	30932474
AllCCS	[M+H]+	192.5	32859911
AllCCS	[M+H-H2O]+	190.3	32859911
AllCCS	[M+NH4]+	194.5	32859911
AllCCS	[M+Na]+	195.0	32859911
AllCCS	[M-H]-	197.7	32859911
AllCCS	[M+Na-2H]-	198.5	32859911
AllCCS	[M+HCOO]-	199.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide	CC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	3908.1	Standard polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide	CC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	2680.9	Standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide	CC(Cl)C(C)(O)C(=O)OC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	2966.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O)OC1=O	2993.0	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TMS,isomer #2	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O[Si](C)(C)C)OC1=O	3010.5	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TMS,isomer #3	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C)C3C)CC2(O)OC1=O	2942.4	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C)C3C)CC2(O)OC1=O	2988.7	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TMS,isomer #2	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O[Si](C)(C)C)OC1=O	3039.3	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TMS,isomer #3	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C)C3C)CC2(O[Si](C)(C)C)OC1=O	2993.3	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,3TMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C)C3C)CC2(O[Si](C)(C)C)OC1=O	3032.0	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O)OC1=O	3238.3	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #2	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	3241.3	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #3	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C(C)(C)C)C3C)CC2(O)OC1=O	3181.0	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C(C)(C)C)C3C)CC2(O)OC1=O	3442.9	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #2	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(C)Cl)C3(C)C(CCC(O)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	3486.7	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #3	CC1=C2C(OC(=O)C(C)(O)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C(C)(C)C)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	3437.0	Semi standard non polar	33892256
3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide,3TBDMS,isomer #1	CC1=C2C(OC(=O)C(C)(O[Si](C)(C)C(C)(C)C)C(C)Cl)C3(C)C(CCC(O[Si](C)(C)C(C)(C)C)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	3685.3	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 - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-4529000000-23fd3dceaf4cf759952d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide GC-MS (3 TMS) - 70eV, Positive	splash10-00b9-5920152000-c4844badf8e80b7c642c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 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 - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-014j-0139300000-166ae6f892fd166b1da0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-00kk-5898100000-48f5f0631cb117c0ca50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-014r-2920000000-f6fd2e15c1600e577cae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-014i-1257900000-2335a4c444a659f1bb83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-0aor-3749100000-b3ee2426370f82a0f50a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0a70-2290000000-e1fade7a461d56fe04b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-015a-0009500000-a8d91049b9dd77ce78c9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-00kb-2198200000-9ea3e5bdd393d1117f28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0cds-3690000000-7ab23b0a147f1fe3daa6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-014r-5410900000-f4dbdf892de0dc2ab932	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-001i-9300100000-70ab0ff3bcd12781f757	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-001i-9000000000-aff380d12baac4fdebf1	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB015424

KNApSAcK ID

Not Available

Chemspider ID

35014160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752004

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 3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide (HMDB0036524)

MOL for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

PDB for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

Structure for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0036524 (3b,8b-Dihydroxy-6b-(3-chloro-2-hydroxy-2-methylbutanoyloxy)-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra