Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:21 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036448

Secondary Accession Numbers

HMDB36448

Metabolite Identification

Common Name

Zedoarondiol

Description

Zedoarondiol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Based on a literature review a significant number of articles have been published on Zedoarondiol.

Structure

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

HMDB0036448
     RDKit          3D
Zedoarondiol
 42 43  0  0  0  0  0  0  0  0999 V2000
    2.7317   -2.5926    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857   -1.0885   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0944   -0.4827   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.3644    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -1.1595    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -0.4499   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578    0.7822    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4193    1.0454   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -0.3436   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -1.3185   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186   -1.6615    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931   -2.4291   -1.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    1.9796    0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    3.2062    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    2.2113    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    1.9938   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.0677   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9346    1.5777    0.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -2.8733    0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -2.9467    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868   -3.0528   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -1.2739   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    0.2665   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -0.0054    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -1.3264    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.1296   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -0.2869   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482    0.6146    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.6977    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.4296   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368   -0.4718   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.5564   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0004   -2.5586    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.9571    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029   -0.8820    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529   -2.3959   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042    3.2933   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547    4.0872    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.1787    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.3960    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    3.0293   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331    1.7505   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 05061309092D          

 18 19  0  0  0  0            999 V2000
    3.3158    0.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986   -0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872    0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    2.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    1.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    0.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    3.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036448

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=C1CC2C(CCC2(C)O)C(C)(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-9(2)10-7-12-11(5-6-14(12,3)17)15(4,18)8-13(10)16/h11-12,17-18H,5-8H2,1-4H3

> <INCHI_KEY>
TXIKNNOOLCGADE-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.3493

> <EXACT_MASS>
252.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.559205633686165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-decahydroazulen-6-one

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.6684790029999998

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.986591548859057

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.357022737543517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.901566956677086

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.38519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036448
     RDKit          3D
Zedoarondiol
 42 43  0  0  0  0  0  0  0  0999 V2000
    2.7317   -2.5926    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857   -1.0885   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0944   -0.4827   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.3644    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -1.1595    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -0.4499   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578    0.7822    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4193    1.0454   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -0.3436   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -1.3185   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186   -1.6615    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931   -2.4291   -1.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    1.9796    0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    3.2062    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    2.2113    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    1.9938   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.0677   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9346    1.5777    0.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -2.8733    0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -2.9467    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868   -3.0528   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -1.2739   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    0.2665   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -0.0054    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -1.3264    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.1296   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -0.2869   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482    0.6146    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.6977    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.4296   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368   -0.4718   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.5564   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0004   -2.5586    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.9571    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029   -0.8820    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529   -2.3959   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042    3.2933   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547    4.0872    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.1787    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.3960    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    3.0293   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331    1.7505   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  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       6.189   0.487   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.104  -1.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.163   0.196   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.001   5.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.463   4.095   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.369   2.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.205   1.119   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.706   4.236   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667   0.257   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.706   1.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.001   3.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.001   2.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.375   2.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.463   1.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.205   4.579   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.915   2.849   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.797   0.833   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.873   5.966   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   14                                                       
CONECT    7   10   12                                                       
CONECT    8   13   15                                                       
CONECT    9    1    2   10                                                  
CONECT   10    7    9   13                                                  
CONECT   11    5   12   15                                                  
CONECT   12    7   11   14                                                  
CONECT   13    8   10   16                                                  
CONECT   14    3    6   12   17                                             
CONECT   15    4    8   11   18                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0036448
HETATM    1  C1  UNL     1       2.732  -2.593   0.044  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.786  -1.088  -0.088  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.094  -0.483  -0.401  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.715  -0.364   0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.479  -1.159   0.348  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.674  -0.450  -0.278  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.158   0.782   0.360  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.419   1.045  -0.483  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.973  -0.344  -0.751  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.937  -1.319  -0.229  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.319  -1.662   1.181  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.793  -2.429  -1.040  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.300   1.980   0.374  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.178   3.206   0.123  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.287   2.211   1.642  1.00  0.00           O  
HETATM   16  C14 UNL     1       0.842   1.994  -0.613  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.867   1.068  -0.081  1.00  0.00           C  
HETATM   18  O3  UNL     1       2.935   1.578   0.275  1.00  0.00           O  
HETATM   19  H1  UNL     1       2.127  -2.873   0.938  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.756  -2.947   0.265  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.287  -3.053  -0.845  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.835  -1.274  -0.708  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.019   0.266  -1.224  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.547  -0.005   0.485  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.439  -1.326   1.416  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.597  -2.130  -0.173  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.457  -0.287  -1.336  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.548   0.615   1.393  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.125   1.698   0.023  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.091   1.430  -1.491  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.937  -0.472  -0.204  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.105  -0.556  -1.820  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.000  -2.559   1.121  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.485  -1.957   1.818  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.903  -0.882   1.691  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.353  -2.396  -1.844  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.504   3.293  -0.909  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.555   4.087   0.408  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.005   3.179   0.865  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.693   1.396   2.008  1.00  0.00           H  
HETATM   41  H23 UNL     1       1.251   3.029  -0.667  1.00  0.00           H  
HETATM   42  H24 UNL     1       0.533   1.751  -1.644  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22   23   24
CONECT    4    5   17
CONECT    5    6   25   26
CONECT    6    7   10   27
CONECT    7    8   13   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   12
CONECT   11   33   34   35
CONECT   12   36
CONECT   13   14   15   16
CONECT   14   37   38   39
CONECT   15   40
CONECT   16   17   41   42
CONECT   17   18   18
END

HMDB0036448
     RDKit          3D
Zedoarondiol
 42 43  0  0  0  0  0  0  0  0999 V2000
    2.7317   -2.5926    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857   -1.0885   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0944   -0.4827   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.3644    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -1.1595    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -0.4499   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578    0.7822    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4193    1.0454   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -0.3436   -0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373   -1.3185   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186   -1.6615    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931   -2.4291   -1.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3001    1.9796    0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    3.2062    0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    2.2113    1.6419 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420    1.9938   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.0677   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9346    1.5777    0.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267   -2.8733    0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -2.9467    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868   -3.0528   -0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -1.2739   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    0.2665   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -0.0054    0.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -1.3264    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.1296   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -0.2869   -1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482    0.6146    1.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.6977    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.4296   -1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368   -0.4718   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.5564   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0004   -2.5586    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.9571    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029   -0.8820    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529   -2.3959   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042    3.2933   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547    4.0872    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    3.1787    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    1.3960    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    3.0293   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331    1.7505   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17  4  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Zedoarondiol	MeSH

Chemical Formula

C₁₅H₂₄O₃

Average Molecular Weight

252.3493

Monoisotopic Molecular Weight

252.172544634

IUPAC Name

1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-decahydroazulen-6-one

Traditional Name

1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one

CAS Registry Number

98644-24-7

SMILES

CC(C)=C1CC2C(CCC2(C)O)C(C)(O)CC1=O

InChI Identifier

InChI=1S/C15H24O3/c1-9(2)10-7-12-11(5-6-14(12,3)17)15(4,18)8-13(10)16/h11-12,17-18H,5-8H2,1-4H3

InChI Key

TXIKNNOOLCGADE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036448)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036448)

Source

Endogenous

Endogenous (HMDB: HMDB0036448)

Plant

Plant (HMDB: HMDB0036448)

Animal

Animal (HMDB: HMDB0036448)

Exogenous

Food

Food (HMDB: HMDB0036448)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036448)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036448)

Cellular process

Cell signaling (HMDB: HMDB0036448)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036448)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036448)

Nutrient

Nutrient (HMDB: HMDB0036448)

Industrial application

Pharmaceutical industry

Anti-inflammatory (HMDB: HMDB0036448)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036448)

Emulsifier (HMDB: HMDB0036448)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	133 - 134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	210.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	1.15	ALOGPS
logP	1.67	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.39 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	2	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]+	160.035	31661259
DarkChem	[M-H]-	158.603	31661259
DeepCCS	[M+H]+	158.459	30932474
DeepCCS	[M-H]-	156.101	30932474
DeepCCS	[M-2H]-	189.094	30932474
DeepCCS	[M+Na]+	164.552	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.7	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	166.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zedoarondiol	CC(C)=C1CC2C(CCC2(C)O)C(C)(O)CC1=O	3010.2	Standard polar	33892256
Zedoarondiol	CC(C)=C1CC2C(CCC2(C)O)C(C)(O)CC1=O	1909.4	Standard non polar	33892256
Zedoarondiol	CC(C)=C1CC2C(CCC2(C)O)C(C)(O)CC1=O	1971.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zedoarondiol,1TMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C)C(C)(O)CC1=O	2078.3	Semi standard non polar	33892256
Zedoarondiol,1TMS,isomer #2	CC(C)=C1CC2C(CCC2(C)O)C(C)(O[Si](C)(C)C)CC1=O	2052.5	Semi standard non polar	33892256
Zedoarondiol,1TMS,isomer #3	CC(C)=C1CC2C(CCC2(C)O)C(C)(O)C=C1O[Si](C)(C)C	2082.1	Semi standard non polar	33892256
Zedoarondiol,2TMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC1=O	2108.8	Semi standard non polar	33892256
Zedoarondiol,2TMS,isomer #2	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C)C(C)(O)C=C1O[Si](C)(C)C	2081.0	Semi standard non polar	33892256
Zedoarondiol,2TMS,isomer #3	CC(C)=C1CC2C(CCC2(C)O)C(C)(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2086.4	Semi standard non polar	33892256
Zedoarondiol,3TMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2123.2	Semi standard non polar	33892256
Zedoarondiol,3TMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2190.1	Standard non polar	33892256
Zedoarondiol,1TBDMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CC1=O	2312.2	Semi standard non polar	33892256
Zedoarondiol,1TBDMS,isomer #2	CC(C)=C1CC2C(CCC2(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CC1=O	2274.7	Semi standard non polar	33892256
Zedoarondiol,1TBDMS,isomer #3	CC(C)=C1CC2C(CCC2(C)O)C(C)(O)C=C1O[Si](C)(C)C(C)(C)C	2307.4	Semi standard non polar	33892256
Zedoarondiol,2TBDMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CC1=O	2527.7	Semi standard non polar	33892256
Zedoarondiol,2TBDMS,isomer #2	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C(C)(C)C)C(C)(O)C=C1O[Si](C)(C)C(C)(C)C	2516.3	Semi standard non polar	33892256
Zedoarondiol,2TBDMS,isomer #3	CC(C)=C1CC2C(CCC2(C)O)C(C)(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2523.0	Semi standard non polar	33892256
Zedoarondiol,3TBDMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2771.9	Semi standard non polar	33892256
Zedoarondiol,3TBDMS,isomer #1	CC(C)=C1CC2C(CCC2(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2684.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarondiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kbo-6970000000-9f78ab2b0c7e04a741f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarondiol GC-MS (2 TMS) - 70eV, Positive	splash10-0fwi-3194000000-a3b5f68326c916b67805	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarondiol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zedoarondiol , positive-QTOF	splash10-0a4i-1900000000-edd6c54a9e54a348c106	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 10V, Positive-QTOF	splash10-0f79-0090000000-7c190435814f4fbbcef8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 20V, Positive-QTOF	splash10-00ku-1390000000-10682457f8c2c2c7cd76	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 40V, Positive-QTOF	splash10-014i-9440000000-3f182865e21d359eb2cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 10V, Negative-QTOF	splash10-0udi-0090000000-fb643c5d37fe9ea1d8c9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 20V, Negative-QTOF	splash10-0ue9-0090000000-b1c0ac0b993ec00ad569	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 40V, Negative-QTOF	splash10-066u-8950000000-06d425e15ef611117f59	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 10V, Negative-QTOF	splash10-0udi-0090000000-96235d738c6453145a08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 20V, Negative-QTOF	splash10-0udi-0090000000-581683be84b15476f66c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 40V, Negative-QTOF	splash10-05o0-5490000000-ba9d1c2f17a34255a164	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 10V, Positive-QTOF	splash10-0udi-0690000000-bccbb7936c3623223896	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 20V, Positive-QTOF	splash10-014r-4390000000-d2bdcfa3e4d373d5a8f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarondiol 40V, Positive-QTOF	splash10-0006-9100000000-8eb40e6d9bf88b2c5404	2021-09-22	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

FDB015335

KNApSAcK ID

C00020357

Chemspider ID

21615460

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14632997

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cho W, Nam JW, Kang HJ, Windono T, Seo EK, Lee KT: Zedoarondiol isolated from the rhizoma of Curcuma heyneana is involved in the inhibition of iNOS, COX-2 and pro-inflammatory cytokines via the downregulation of NF-kappaB pathway in LPS-stimulated murine macrophages. Int Immunopharmacol. 2009 Aug;9(9):1049-57. doi: 10.1016/j.intimp.2009.04.012. Epub 2009 Apr 24. [PubMed:19398040 ]
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 Zedoarondiol (HMDB0036448)

MOL for HMDB0036448 (Zedoarondiol)

3D MOL for HMDB0036448 (Zedoarondiol)

3D SDF for HMDB0036448 (Zedoarondiol)

3D-SDF for HMDB0036448 (Zedoarondiol)

PDB for HMDB0036448 (Zedoarondiol)

3D PDB for HMDB0036448 (Zedoarondiol)

SMILES for HMDB0036448 (Zedoarondiol)

INCHI for HMDB0036448 (Zedoarondiol)

Structure for HMDB0036448 (Zedoarondiol)

3D Structure for HMDB0036448 (Zedoarondiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra