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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:50:43 UTC

Update Date

2021-09-26 23:00:06 UTC

HMDB ID

HMDB0249338

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bolandiol

Description

15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-diol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Based on a literature review very few articles have been published on 15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bolandiol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bolandiol 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

HMDB0249338
     RDKit          3D
Bolandiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.5951   -0.9866    1.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -0.4318    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393   -1.3853   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -1.0743   -0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641   -0.5393    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -0.5617    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4073   -1.4349   -0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -1.6291   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874   -0.5171    0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710   -0.2808    0.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    0.7606    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    0.7718    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201    2.0641    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    1.8781   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217    0.8332    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    0.9046    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971    1.6552   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.8996   -1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587   -0.0077    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6432   -1.0760   -0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -0.4225    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.0413    1.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397   -0.8528    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483   -2.3941    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.5285   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -0.3945   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0697   -2.0379   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -1.1890    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911   -0.9796    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -2.4708   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -1.0443   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4121   -1.8136   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -2.5644    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -0.7421    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    0.5228   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    1.7058    0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.4746    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817    2.8226   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    1.5223   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    2.7845   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    1.1124    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328    1.4049    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    1.8313   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970    2.6712   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.3279   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3360    1.5916   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    0.6214    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.7607   -0.3131 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END


  Mrv1652309112105512D          

 20 23  0  0  0  0            999 V2000
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  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
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249338

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=CC(O)CCC34)C1CCC2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3

> <INCHI_KEY>
CMXKUJNZWYTFJN-UHFFFAOYSA-N

> <FORMULA>
C18H28O2

> <MOLECULAR_WEIGHT>
276.42

> <EXACT_MASS>
276.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.91300925392109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.654037689666666

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37770530193098

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.524960806331435

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8215065576130297

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
80.8521

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249338
     RDKit          3D
Bolandiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.5951   -0.9866    1.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -0.4318    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393   -1.3853   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -1.0743   -0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641   -0.5393    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -0.5617    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4073   -1.4349   -0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -1.6291   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874   -0.5171    0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710   -0.2808    0.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    0.7606    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    0.7718    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201    2.0641    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    1.8781   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217    0.8332    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    0.9046    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971    1.6552   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.8996   -1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587   -0.0077    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6432   -1.0760   -0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -0.4225    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.0413    1.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397   -0.8528    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483   -2.3941    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.5285   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -0.3945   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0697   -2.0379   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -1.1890    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911   -0.9796    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -2.4708   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -1.0443   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4121   -1.8136   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -2.5644    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -0.7421    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    0.5228   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    1.7058    0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.4746    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817    2.8226   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    1.5223   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    2.7845   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    1.1124    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328    1.4049    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    1.8313   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970    2.6712   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.3279   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3360    1.5916   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    0.6214    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.7607   -0.3131 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.882   3.020   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5   14                                                  
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0249338
HETATM    1  C1  UNL     1      -2.595  -0.987   1.898  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.479  -0.432   0.508  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.839  -1.385  -0.455  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.385  -1.074  -0.759  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.264  -0.539   0.483  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.738  -0.562   0.525  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.407  -1.435  -0.504  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.862  -1.629  -0.185  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.487  -0.517   0.578  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.771  -0.281   0.087  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.732   0.761   0.479  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.395   0.772   0.452  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.720   2.064   0.355  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.315   1.878  -0.161  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.322   0.833   0.749  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.787   0.905   0.602  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.297   1.655  -0.581  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.507   0.900  -1.120  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.859  -0.008   0.021  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.643  -1.076  -0.332  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.979  -0.422   2.643  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.273  -2.041   1.986  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.640  -0.853   2.238  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.848  -2.394   0.050  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.429  -1.529  -1.391  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.283  -0.395  -1.628  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.070  -2.038  -1.065  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.133  -1.189   1.322  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.091  -0.980   1.519  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.970  -2.471  -0.535  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.327  -1.044  -1.526  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.412  -1.814  -1.136  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.999  -2.564   0.422  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.568  -0.742   1.674  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.788   0.523  -0.484  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.262   1.706   0.429  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.623   2.475   1.392  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.282   2.823  -0.228  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.409   1.522  -1.204  1.00  0.00           H  
HETATM   40  H20 UNL     1      -0.283   2.785  -0.148  1.00  0.00           H  
HETATM   41  H21 UNL     1      -0.019   1.112   1.779  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.233   1.405   1.515  1.00  0.00           H  
HETATM   43  H23 UNL     1      -1.591   1.831  -1.385  1.00  0.00           H  
HETATM   44  H24 UNL     1      -2.697   2.671  -0.289  1.00  0.00           H  
HETATM   45  H25 UNL     1      -3.147   0.328  -2.010  1.00  0.00           H  
HETATM   46  H26 UNL     1      -4.336   1.592  -1.397  1.00  0.00           H  
HETATM   47  H27 UNL     1      -4.295   0.621   0.825  1.00  0.00           H  
HETATM   48  H28 UNL     1      -5.595  -0.761  -0.313  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7   12   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   11   34
CONECT   10   35
CONECT   11   12   12   36
CONECT   12   13
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41
CONECT   16   17   42
CONECT   17   18   43   44
CONECT   18   19   45   46
CONECT   19   20   47
CONECT   20   48
END

HMDB0249338
     RDKit          3D
Bolandiol
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.5951   -0.9866    1.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -0.4318    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393   -1.3853   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -1.0743   -0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641   -0.5393    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -0.5617    0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4073   -1.4349   -0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -1.6291   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874   -0.5171    0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710   -0.2808    0.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    0.7606    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    0.7718    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7201    2.0641    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148    1.8781   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217    0.8332    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    0.9046    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971    1.6552   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.8996   -1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587   -0.0077    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6432   -1.0760   -0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786   -0.4225    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728   -2.0413    1.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397   -0.8528    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483   -2.3941    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.5285   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832   -0.3945   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0697   -2.0379   -1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1327   -1.1890    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911   -0.9796    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -2.4708   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -1.0443   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4121   -1.8136   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -2.5644    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5685   -0.7421    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    0.5228   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    1.7058    0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.4746    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817    2.8226   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    1.5223   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2834    2.7845   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    1.1124    1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2328    1.4049    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    1.8313   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970    2.6712   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.3279   -2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3360    1.5916   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    0.6214    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949   -0.7607   -0.3131 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₈O₂

Average Molecular Weight

276.42

Monoisotopic Molecular Weight

276.208930142

IUPAC Name

15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

Traditional Name

15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=CC(O)CCC34)C1CCC2O

InChI Identifier

InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3

InChI Key

CMXKUJNZWYTFJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
17-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-4-steroid
Delta-4-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	2.61	ALOGPS
logP	2.65	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.52	ChemAxon
pKa (Strongest Basic)	-0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.85 m³·mol⁻¹	ChemAxon
Polarizability	32.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	197.645	30932474
DeepCCS	[M+Na]+	173.21	30932474
AllCCS	[M+H]+	172.3	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	175.3	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bolandiol	CC12CCC3C(CCC4=CC(O)CCC34)C1CCC2O	2726.5	Standard polar	33892256
Bolandiol	CC12CCC3C(CCC4=CC(O)CCC34)C1CCC2O	2433.2	Standard non polar	33892256
Bolandiol	CC12CCC3C(CCC4=CC(O)CCC34)C1CCC2O	2502.0	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 - Bolandiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-067j-0290000000-cad2103937cae44c78b0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bolandiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Bolandiol 10V, Positive-QTOF	splash10-056r-0090000000-a733b5247bc04c07260a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolandiol 20V, Positive-QTOF	splash10-0006-0290000000-c8471f46dcd266d3c616	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolandiol 40V, Positive-QTOF	splash10-004i-1900000000-39ad2ab9b721f19a9387	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolandiol 10V, Negative-QTOF	splash10-004i-0090000000-4d3066b364d5c97a28e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolandiol 20V, Negative-QTOF	splash10-004i-0090000000-8d47daf62e3a289f59bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bolandiol 40V, Negative-QTOF	splash10-00di-0190000000-9391cfdd6512786864bd	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

23750

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25440

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 Bolandiol (HMDB0249338)

MOL for HMDB0249338 (Bolandiol)

3D MOL for HMDB0249338 (Bolandiol)

3D SDF for HMDB0249338 (Bolandiol)

3D-SDF for HMDB0249338 (Bolandiol)

PDB for HMDB0249338 (Bolandiol)

3D PDB for HMDB0249338 (Bolandiol)

SMILES for HMDB0249338 (Bolandiol)

INCHI for HMDB0249338 (Bolandiol)

Structure for HMDB0249338 (Bolandiol)

3D Structure for HMDB0249338 (Bolandiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra