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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:14:35 UTC

Update Date

2022-03-07 02:57:04 UTC

HMDB ID

HMDB0041551

Secondary Accession Numbers

HMDB41551

Metabolite Identification

Common Name

3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide

Description

3,8-Dihydroxy-6-methoxy-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 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide.

Structure

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

HMDB0041551
     RDKit          3D
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2539    2.9348   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    1.6292   -0.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204    0.7017    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.0688    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852   -0.0995    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    0.3518    2.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052   -0.8307   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895   -1.1701    0.0266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.0643   -1.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -0.5281   -1.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    0.5374   -2.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7782   -1.4922   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125   -0.8088   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -1.6328   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.7327   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.3020   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043    1.5728   -0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -0.1324    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523    0.7695    1.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -0.4144    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -1.5601    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    3.6635   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    3.1734    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982    3.0406    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113    1.1568    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591    1.1795    2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645    0.7417    2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015   -0.5096    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330    0.2433   -3.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.4771   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.6540   -2.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.1283   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110   -2.5453   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -1.9179   -2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348   -1.3826   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807   -0.1825   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227    0.3237    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    2.0899   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -1.1245    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.8299    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    0.4091    2.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    1.7814    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -2.3838    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8657    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -1.1199    2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 10  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

  Mrv0541 05061312452D          

 21 23  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
    2.0701    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    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
    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
    2.0701    1.9354    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
    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
    0.5549    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
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041551

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-8-12-13(20-4)15(3)9(2)11(17)6-5-10(15)7-16(12,19)21-14(8)18/h9-11,13,17,19H,5-7H2,1-4H3

> <INCHI_KEY>
PVRCOBIICILOMH-UHFFFAOYSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.3588

> <EXACT_MASS>
296.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.379172340750205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9a-dihydroxy-4-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.5230559600000007

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.93682156740634

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.186209835836038

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8264718982148276

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.43169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9a-dihydroxy-4-methoxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041551
     RDKit          3D
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2539    2.9348   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    1.6292   -0.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204    0.7017    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.0688    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852   -0.0995    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    0.3518    2.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052   -0.8307   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895   -1.1701    0.0266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.0643   -1.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -0.5281   -1.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    0.5374   -2.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7782   -1.4922   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125   -0.8088   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -1.6328   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.7327   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.3020   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043    1.5728   -0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -0.1324    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523    0.7695    1.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -0.4144    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -1.5601    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    3.6635   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    3.1734    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982    3.0406    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113    1.1568    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591    1.1795    2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645    0.7417    2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015   -0.5096    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330    0.2433   -3.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.4771   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.6540   -2.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.1283   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110   -2.5453   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -1.9179   -2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348   -1.3826   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807   -0.1825   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227    0.3237    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    2.0899   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -1.1245    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.8299    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    0.4091    2.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    1.7814    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -2.3838    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8657    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -1.1199    2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 10  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  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       3.864   5.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.036   0.541   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   20                                                            
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   10   16                                                       
CONECT    8    1   12   14                                                  
CONECT    9    2   11   15                                                  
CONECT   10    5    7   15                                                  
CONECT   11    6    9   17                                                  
CONECT   12    8   13   16                                                  
CONECT   13   12   15   20                                                  
CONECT   14    8   18   21                                                  
CONECT   15    3    9   10   13                                             
CONECT   16    7   12   19   21                                             
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   16                                                            
CONECT   20    4   13                                                       
CONECT   21   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0041551
HETATM    1  C1  UNL     1       0.254   2.935  -0.096  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.299   1.629  -0.575  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.520   0.702   0.427  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.842   0.069   0.083  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.985  -0.099   0.683  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.325   0.352   2.041  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.905  -0.831  -0.211  1.00  0.00           C  
HETATM    8  O2  UNL     1       5.090  -1.170   0.027  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.182  -1.064  -1.372  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.898  -0.528  -1.295  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.719   0.537  -2.197  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.778  -1.492  -1.527  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.513  -0.809  -1.144  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.726  -1.633  -1.488  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.933  -0.733  -1.380  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.817   0.302  -0.310  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.604   1.573  -0.769  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.849  -0.132   0.786  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.952   0.769   1.987  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.475  -0.414   0.317  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.081  -1.560   1.168  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.077   3.663  -0.909  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.181   3.173   0.446  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.598   3.041   0.606  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.611   1.157   1.427  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.659   1.179   2.374  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.365   0.742   2.059  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.201  -0.510   2.725  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.833   0.243  -3.129  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.911  -2.477  -1.081  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.717  -1.654  -2.641  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.572   0.128  -1.733  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.811  -2.545  -0.883  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.631  -1.918  -2.554  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.835  -1.383  -1.267  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.081  -0.183  -2.354  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.823   0.324   0.210  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.444   2.090  -0.860  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.282  -1.125   1.127  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.031   0.830   2.584  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.744   0.409   2.710  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.336   1.781   1.673  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.646  -2.384   1.260  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.080  -1.866   0.860  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.189  -1.120   2.200  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4   20   25
CONECT    4    5    5   10
CONECT    5    6    7
CONECT    6   26   27   28
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   30   31
CONECT   13   14   20   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   18   37
CONECT   17   38
CONECT   18   19   20   39
CONECT   19   40   41   42
CONECT   20   21
CONECT   21   43   44   45
END

HMDB0041551
     RDKit          3D
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide
 45 47  0  0  0  0  0  0  0  0999 V2000
    0.2539    2.9348   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2994    1.6292   -0.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204    0.7017    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.0688    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852   -0.0995    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    0.3518    2.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052   -0.8307   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895   -1.1701    0.0266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.0643   -1.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -0.5281   -1.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    0.5374   -2.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7782   -1.4922   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125   -0.8088   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -1.6328   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.7327   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.3020   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043    1.5728   -0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -0.1324    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523    0.7695    1.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750   -0.4144    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813   -1.5601    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    3.6635   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    3.1734    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5982    3.0406    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113    1.1568    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591    1.1795    2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645    0.7417    2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015   -0.5096    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330    0.2433   -3.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.4771   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172   -1.6540   -2.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    0.1283   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8110   -2.5453   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312   -1.9179   -2.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348   -1.3826   -1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0807   -0.1825   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227    0.3237    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    2.0899   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -1.1245    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.8299    2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    0.4091    2.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    1.7814    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -2.3838    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8657    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -1.1199    2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 10  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄O₅

Average Molecular Weight

296.3588

Monoisotopic Molecular Weight

296.162373878

IUPAC Name

6,9a-dihydroxy-4-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

6,9a-dihydroxy-4-methoxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

COC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C

InChI Identifier

InChI=1S/C16H24O5/c1-8-12-13(20-4)15(3)9(2)11(17)6-5-10(15)7-16(12,19)21-14(8)18/h9-11,13,17,19H,5-7H2,1-4H3

InChI Key

PVRCOBIICILOMH-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
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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: HMDB0041551)

Source

Endogenous

Endogenous (HMDB: HMDB0041551)

Plant

Plant (HMDB: HMDB0041551)

Animal

Animal (HMDB: HMDB0041551)

Exogenous

Food

Food (HMDB: HMDB0041551)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0041551)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0041551)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0041551)

Lipid metabolism pathway (HMDB: HMDB0041551)

Cellular process

Cell signaling (HMDB: HMDB0041551)

Biochemical process

Lipid transport (HMDB: HMDB0041551)

Role

Biological role

Energy source (HMDB: HMDB0041551)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041551)

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	2.3 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.52	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.43 m³·mol⁻¹	ChemAxon
Polarizability	31.38 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
DarkChem	[M+H]+	168.656	31661259
DarkChem	[M-H]-	168.003	31661259
DeepCCS	[M-2H]-	201.299	30932474
DeepCCS	[M+Na]+	176.526	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide	COC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	3491.4	Standard polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide	COC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	2283.6	Standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide	COC1C2=C(C)C(=O)OC2(O)CC2CCC(O)C(C)C12C	2394.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	COC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)CC2CCC(O)C(C)C21C	2401.9	Semi standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #2	COC1C2=C(C)C(=O)OC2(O)CC2CCC(O[Si](C)(C)C)C(C)C21C	2352.3	Semi standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	COC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)CC2CCC(O[Si](C)(C)C)C(C)C21C	2444.0	Semi standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	COC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)CC2CCC(O)C(C)C21C	2625.3	Semi standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #2	COC1C2=C(C)C(=O)OC2(O)CC2CCC(O[Si](C)(C)C(C)(C)C)C(C)C21C	2585.9	Semi standard non polar	33892256
3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	COC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)CC2CCC(O[Si](C)(C)C(C)(C)C)C(C)C21C	2882.7	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 - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uyi-0390000000-c32dc7abde7669edf3c9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide GC-MS (2 TMS) - 70eV, Positive	splash10-05dm-9188600000-a0e9de8383f4ec428d9e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-Dihydroxy-6-methoxy-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 - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-004j-0090000000-15dada739b125cde9fbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-0fba-2090000000-16383624c325a0d2b1d0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0f7c-2910000000-e722e1263d47d07e6df2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-1f91bf6c8b1903621d4d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-0f92-0090000000-ed4bad38ff5590093ee6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0550-2590000000-eb3179068cd7ef43b5c4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-d119a7ee6aef23a1a76a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-0002-0090000000-d9628b6c4ee4d7a71cc6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-00ks-2790000000-6dd0431f2304f91362cc	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-002b-0090000000-3eefac8f8c18e3110b9d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-0002-0190000000-022499c248f7d8814fba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0uea-3980000000-d1348e655cf60beebc03	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

FDB021534

KNApSAcK ID

Not Available

Chemspider ID

35015202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85265509

PDB ID

Not Available

ChEBI ID

174828

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 3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide (HMDB0041551)

MOL for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

PDB for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

Structure for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0041551 (3,8-Dihydroxy-6-methoxy-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra