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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:58 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029530

Secondary Accession Numbers

HMDB29530

Metabolite Identification

Common Name

Glabrene

Description

Glabrene belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Based on a literature review a significant number of articles have been published on Glabrene.

Structure

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

HMDB0029530
     RDKit          3D
Glabrene
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.3312    2.1367    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    0.7874    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    1.0187    2.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462   -0.0947    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2315   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.6676   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -2.8803   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -3.6607   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -3.2878   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.4606   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -1.2609   -0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.3703   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899   -0.6808   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476    0.1328   -0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445   -0.2299   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121    0.5707   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.7670    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5646    2.6013    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1885    2.1175    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.3252    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    1.6658    0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672    0.9099    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -0.8768   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7642    0.3170    0.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    2.3621    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010    1.9811   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    2.9254    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    1.1827    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.1493    2.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8509    1.8889    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563    0.2207    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7302   -1.9079   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -4.5394   -2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -4.2220   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018   -2.7911   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -1.6139   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -1.1778   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    0.2639   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    3.2844    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    3.0609    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0592    1.5641   -0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426    0.7204    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 11 23  2  0
 23 24  1  0
 24  2  1  0
 23  6  1  0
 22 12  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
M  END


  Mrv0541 02241218072D          

 24 27  0  0  0  0            999 V2000
   -2.4992    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -0.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -1.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -1.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -0.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005    0.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005    1.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -0.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9133   -1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148    1.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -1.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 23  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029530

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2OC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20(2)8-7-16-17(22)6-5-15(19(16)24-20)13-9-12-3-4-14(21)10-18(12)23-11-13/h3-10,21-22H,11H2,1-2H3

> <INCHI_KEY>
NGGYSPUAKQMTNP-UHFFFAOYSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.3545

> <EXACT_MASS>
322.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.07498492471448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(7-hydroxy-2H-chromen-3-yl)-2,2-dimethyl-2H-chromen-5-ol

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
3.986108861333333

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.743105974207852

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.129382801095653

> <JCHEM_PKA_STRONGEST_BASIC>
-4.611443392843117

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
94.12660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(7-hydroxy-2H-chromen-3-yl)-2,2-dimethylchromen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029530
     RDKit          3D
Glabrene
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.3312    2.1367    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    0.7874    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    1.0187    2.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462   -0.0947    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2315   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.6676   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -2.8803   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -3.6607   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -3.2878   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.4606   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -1.2609   -0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.3703   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899   -0.6808   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476    0.1328   -0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445   -0.2299   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121    0.5707   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.7670    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5646    2.6013    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1885    2.1175    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.3252    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    1.6658    0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672    0.9099    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -0.8768   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7642    0.3170    0.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    2.3621    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010    1.9811   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    2.9254    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    1.1827    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.1493    2.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8509    1.8889    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563    0.2207    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7302   -1.9079   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -4.5394   -2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -4.2220   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018   -2.7911   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -1.6139   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -1.1778   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    0.2639   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    3.2844    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    3.0609    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0592    1.5641   -0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426    0.7204    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 11 23  2  0
 23 24  1  0
 24  2  1  0
 23  6  1  0
 22 12  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.665   0.285   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.665  -1.256   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.332  -2.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -1.256   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.332   1.053   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.668  -2.027   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.663  -1.256   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.663   0.285   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.668   1.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.998   1.056   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334   0.285   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.668   1.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.668   2.595   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.334   3.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.998   2.595   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.334  -1.256   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.668  -2.029   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.001  -1.256   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.001   0.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.897  -3.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.438  -3.365   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.001   3.365   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.001  -2.027   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17   12   18                                                       
CONECT   18   17   19   21   22                                             
CONECT   19   18   20                                                       
CONECT   20   13   19                                                       
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23   14                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0029530
HETATM    1  C1  UNL     1      -3.331   2.137   0.005  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.031   0.787   0.645  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.177   1.019   2.153  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.146  -0.095   0.264  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.924  -1.231  -0.340  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.575  -1.668  -0.657  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.345  -2.880  -1.302  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.456  -3.661  -1.630  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.070  -3.288  -1.600  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.004  -2.461  -1.244  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.169  -1.261  -0.610  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.932  -0.370  -0.227  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.190  -0.681  -0.489  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.348   0.133  -0.151  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.644  -0.230  -0.443  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.712   0.571  -0.105  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.488   1.767   0.542  1.00  0.00           C  
HETATM   18  O2  UNL     1       6.565   2.601   0.897  1.00  0.00           O  
HETATM   19  C17 UNL     1       4.188   2.117   0.827  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.105   1.325   0.494  1.00  0.00           C  
HETATM   21  O3  UNL     1       1.810   1.666   0.773  1.00  0.00           O  
HETATM   22  C19 UNL     1       0.667   0.910   0.479  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.465  -0.877  -0.323  1.00  0.00           C  
HETATM   24  O4  UNL     1      -1.764   0.317   0.315  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.390   2.362   0.254  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.301   1.981  -1.110  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.660   2.925   0.343  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.177   1.183   2.570  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.658   0.149   2.650  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.851   1.889   2.356  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.156   0.221   0.496  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.730  -1.908  -0.636  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.387  -4.539  -2.091  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.883  -4.222  -2.097  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.002  -2.791  -1.483  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.421  -1.614  -0.999  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.826  -1.178  -0.955  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.702   0.264  -0.343  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.830   3.284   0.189  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.012   3.061   1.336  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.059   1.564  -0.209  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.143   0.720   1.453  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   23   23
CONECT   12   13   13   22
CONECT   13   14   36
CONECT   14   15   15   20
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18   19
CONECT   18   39
CONECT   19   20   20   40
CONECT   20   21
CONECT   21   22
CONECT   22   41   42
CONECT   23   24
END

HMDB0029530
     RDKit          3D
Glabrene
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.3312    2.1367    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    0.7874    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    1.0187    2.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462   -0.0947    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2315   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.6676   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -2.8803   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -3.6607   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -3.2878   -1.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.4606   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -1.2609   -0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.3703   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899   -0.6808   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476    0.1328   -0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445   -0.2299   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121    0.5707   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.7670    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5646    2.6013    0.8968 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1885    2.1175    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.3252    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    1.6658    0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672    0.9099    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -0.8768   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7642    0.3170    0.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904    2.3621    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010    1.9811   -1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    2.9254    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775    1.1827    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.1493    2.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8509    1.8889    2.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563    0.2207    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7302   -1.9079   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -4.5394   -2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -4.2220   -2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018   -2.7911   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -1.6139   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -1.1778   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    0.2639   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    3.2844    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    3.0609    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0592    1.5641   -0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1426    0.7204    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 11 23  2  0
 23 24  1  0
 24  2  1  0
 23  6  1  0
 22 12  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',2'-Dimethyl-2H,2'H-(3,8')bi(1-benzopyranyl)-7,5'-diol	HMDB
2',2'-Dimethyl-2H,2'H-[3,8']bi[1-benzopyranyl]-7,5'-diol	HMDB
2',2'-Dimethyl[3,8'-bi-2H-1-benzopyran]-5',7-diol, 9ci	HMDB
Glabrene	MeSH

Chemical Formula

C₂₀H₁₈O₄

Average Molecular Weight

322.3545

Monoisotopic Molecular Weight

322.120509064

IUPAC Name

8-(7-hydroxy-2H-chromen-3-yl)-2,2-dimethyl-2H-chromen-5-ol

Traditional Name

8-(7-hydroxy-2H-chromen-3-yl)-2,2-dimethylchromen-5-ol

CAS Registry Number

60008-03-9

SMILES

CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2OC1

InChI Identifier

InChI=1S/C20H18O4/c1-20(2)8-7-16-17(22)6-5-15(19(16)24-20)13-9-12-3-4-14(21)10-18(12)23-11-13/h3-10,21-22H,11H2,1-2H3

InChI Key

NGGYSPUAKQMTNP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Hydroxyisoflavonoid
Isoflav-3-ene skeleton
2,2-dimethyl-1-benzopyran
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029530)

Cellular substructure

Membrane (HMDB: HMDB0029530)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029530)

Source

Endogenous

Endogenous (HMDB: HMDB0029530)

Plant

Plant (HMDB: HMDB0029530)

Exogenous

Food

Food (HMDB: HMDB0029530)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 203 °C	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	0.0093 g/L	ALOGPS
logP	3.68	ALOGPS
logP	3.99	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.13 m³·mol⁻¹	ChemAxon
Polarizability	35.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.72	31661259
DarkChem	[M-H]-	174.188	31661259
DeepCCS	[M+H]+	173.0	30932474
DeepCCS	[M-H]-	170.642	30932474
DeepCCS	[M-2H]-	204.532	30932474
DeepCCS	[M+Na]+	179.76	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.1	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	180.5	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glabrene	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2OC1	3960.7	Standard polar	33892256
Glabrene	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2OC1	2898.0	Standard non polar	33892256
Glabrene	CC1(C)OC2=C(C=CC(O)=C2C=C1)C1=CC2=CC=C(O)C=C2OC1	3193.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glabrene,1TMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C)C=CC(C3=CC4=CC=C(O)C=C4OC3)=C2O1	2997.1	Semi standard non polar	33892256
Glabrene,1TMS,isomer #2	CC1(C)C=CC2=C(O)C=CC(C3=CC4=CC=C(O[Si](C)(C)C)C=C4OC3)=C2O1	2976.5	Semi standard non polar	33892256
Glabrene,2TMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C)C=CC(C3=CC4=CC=C(O[Si](C)(C)C)C=C4OC3)=C2O1	2927.0	Semi standard non polar	33892256
Glabrene,1TBDMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C=CC(C3=CC4=CC=C(O)C=C4OC3)=C2O1	3270.3	Semi standard non polar	33892256
Glabrene,1TBDMS,isomer #2	CC1(C)C=CC2=C(O)C=CC(C3=CC4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OC3)=C2O1	3248.0	Semi standard non polar	33892256
Glabrene,2TBDMS,isomer #1	CC1(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C=CC(C3=CC4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OC3)=C2O1	3463.7	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 - Glabrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-0495000000-e03f71738095583625d9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glabrene GC-MS (2 TMS) - 70eV, Positive	splash10-0zml-5159600000-5a3918af85dc78822d83	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glabrene 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 - Glabrene 10V, Positive-QTOF	splash10-00di-0129000000-c87f7c62836517f3760c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 20V, Positive-QTOF	splash10-00di-1964000000-8d52b7dae333307c260e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 40V, Positive-QTOF	splash10-0aor-5970000000-46a2bef4b1221c37b038	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 10V, Negative-QTOF	splash10-00di-0009000000-363c0bafec7c93646c24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 20V, Negative-QTOF	splash10-00fr-1849000000-0dea319a2b82c5bb07ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 40V, Negative-QTOF	splash10-0a4r-0590000000-3ed45da8dbb8763b0238	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 10V, Positive-QTOF	splash10-00di-0009000000-17eb34705e2ef23f703b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 20V, Positive-QTOF	splash10-00di-0059000000-894c03ecce09c3dc22a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 40V, Positive-QTOF	splash10-05o0-1291000000-57c35197174af3fe00e6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 10V, Negative-QTOF	splash10-00di-0009000000-a4f58630e05faac231a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 20V, Negative-QTOF	splash10-00di-0009000000-22df309a364997384205	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glabrene 40V, Negative-QTOF	splash10-004i-0190000000-99f55e7828c1c8089997	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB000671

KNApSAcK ID

C00009755

Chemspider ID

421858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glabrene

METLIN ID

Not Available

PubChem Compound

480774

PDB ID

Not Available

ChEBI ID

603420

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Glabrene (HMDB0029530)

MOL for HMDB0029530 (Glabrene)

3D MOL for HMDB0029530 (Glabrene)

3D SDF for HMDB0029530 (Glabrene)

3D-SDF for HMDB0029530 (Glabrene)

PDB for HMDB0029530 (Glabrene)

3D PDB for HMDB0029530 (Glabrene)

SMILES for HMDB0029530 (Glabrene)

INCHI for HMDB0029530 (Glabrene)

Structure for HMDB0029530 (Glabrene)

3D Structure for HMDB0029530 (Glabrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra