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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:14:24 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037969

Secondary Accession Numbers

HMDB37969

Metabolite Identification

Common Name

Urodiolenone

Description

Urodiolenone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on Urodiolenone.

Structure

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

HMDB0037969
     RDKit          3D
Urodiolenone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.2705    2.1996    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    0.6896    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.2433    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -1.2215    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835   -1.8142    2.0578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515   -2.0213    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053   -1.4548   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343   -2.2649   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -1.6583   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -0.4510    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    0.2379   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.7427   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    0.5962   -1.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    1.4892    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    1.2183    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0884    0.5222    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -0.0063   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    0.2766   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120    2.6980    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    2.5189   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117    2.4833    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.4683   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.7074    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5461    2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1245   -3.1127    0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -3.3085   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -2.4005   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -2.4751   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -1.4662   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -0.7925    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323   -1.4311    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -0.1348    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.2447   -1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    1.3782   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7295    1.8931    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.2776    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    2.0791    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.4063   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    0.9166    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    1.3116   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4333   -2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3891    0.2769   -2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

(+)-Nootkatone-13,14-diol
  Mrv1572001071617242D          

 18 19  0  0  0  0            999 V2000
   -2.8580    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870    1.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580   -1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -1.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  2 11  2  0  0  0  0
  4 12  1  0  0  0  0
  5 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037969

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C=C2CCC(CC12C)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-10-6-13(17)7-11-4-5-12(8-14(10,11)2)15(3,18)9-16/h7,10,12,16,18H,4-6,8-9H2,1-3H3

> <INCHI_KEY>
DJPISZPEZJGKKI-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.56305370523997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(1,2-dihydroxypropan-2-yl)-4,4a-dimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.6074117019999996

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.380167141768734

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.871590444310204

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0715532782015496

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.5958

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1,2-dihydroxypropan-2-yl)-4,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037969
     RDKit          3D
Urodiolenone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.2705    2.1996    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    0.6896    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.2433    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -1.2215    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835   -1.8142    2.0578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515   -2.0213    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053   -1.4548   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343   -2.2649   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -1.6583   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -0.4510    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    0.2379   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.7427   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    0.5962   -1.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    1.4892    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    1.2183    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0884    0.5222    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -0.0063   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    0.2766   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120    2.6980    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    2.5189   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117    2.4833    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.4683   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.7074    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5461    2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1245   -3.1127    0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -3.3085   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -2.4005   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -2.4751   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -1.4662   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -0.7925    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323   -1.4311    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -0.1348    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.2447   -1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    1.3782   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7295    1.8931    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.2776    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    2.0791    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.4063   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    0.9166    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    1.3116   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4333   -2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3891    0.2769   -2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: (+)-Nootkatone-13,14-diol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -5.335   1.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.669   1.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.669  -0.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -1.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   1.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.668   1.980   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.668  -1.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   1.210   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.002   1.980   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335  -2.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.015  -1.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -1.100   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.333  -0.330   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -2.640   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.333  -1.870   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -1.100   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8   13                                             
CONECT    6    1    5    7                                                  
CONECT    7   10    6                                                       
CONECT    8    9    5                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    7                                                       
CONECT   11    2                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    9   15   16   17                                             
CONECT   15   14   18                                                       
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0037969
HETATM    1  C1  UNL     1      -2.271   2.200   0.165  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.432   0.690   0.248  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.905   0.243   1.587  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.132  -1.221   1.522  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.083  -1.814   2.058  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.151  -2.021   0.766  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.305  -1.455  -0.061  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.334  -2.265  -0.805  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.033  -1.658  -0.733  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.206  -0.451   0.112  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.495   0.238  -0.302  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.656  -0.743  -0.090  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.385   0.596  -1.624  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.743   1.489   0.515  1.00  0.00           C  
HETATM   15  O3  UNL     1       2.865   1.218   1.859  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.088   0.522   0.165  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.240  -0.006  -0.314  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.304   0.277  -1.831  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.012   2.698   0.791  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.420   2.519  -0.894  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.212   2.483   0.415  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.284   0.468  -0.466  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.898   0.707   1.763  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.257   0.546   2.422  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.124  -3.113   0.892  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.354  -3.309  -0.400  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.669  -2.401  -1.876  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.720  -2.475  -0.380  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.351  -1.466  -1.780  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.407  -0.792   1.159  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.432  -1.431   0.752  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.535  -0.135   0.225  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.826  -1.245  -1.046  1.00  0.00           H  
HETATM   34  H16 UNL     1       2.936   1.378  -1.791  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.729   1.893   0.141  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.006   2.278   0.267  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.796   2.079   2.348  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.318   1.406  -0.463  1.00  0.00           H  
HETATM   39  H21 UNL     1      -0.094   0.917   1.188  1.00  0.00           H  
HETATM   40  H22 UNL     1      -0.938   1.312  -1.964  1.00  0.00           H  
HETATM   41  H23 UNL     1      -0.717  -0.433  -2.408  1.00  0.00           H  
HETATM   42  H24 UNL     1      -2.389   0.277  -2.132  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   17   22
CONECT    3    4   23   24
CONECT    4    5    5    6
CONECT    6    7    7   25
CONECT    7    8   17
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   16   30
CONECT   11   12   13   14
CONECT   12   31   32   33
CONECT   13   34
CONECT   14   15   35   36
CONECT   15   37
CONECT   16   17   38   39
CONECT   17   18
CONECT   18   40   41   42
END

HMDB0037969
     RDKit          3D
Urodiolenone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.2705    2.1996    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    0.6896    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9054    0.2433    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -1.2215    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835   -1.8142    2.0578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515   -2.0213    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053   -1.4548   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343   -2.2649   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -1.6583   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -0.4510    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    0.2379   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.7427   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    0.5962   -1.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    1.4892    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    1.2183    1.8588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0884    0.5222    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -0.0063   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    0.2766   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120    2.6980    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204    2.5189   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117    2.4833    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.4683   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.7074    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.5461    2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1245   -3.1127    0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -3.3085   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -2.4005   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202   -2.4751   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -1.4662   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -0.7925    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323   -1.4311    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348   -0.1348    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.2447   -1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9355    1.3782   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7295    1.8931    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.2776    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    2.0791    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    1.4063   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    0.9166    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    1.3116   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4333   -2.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3891    0.2769   -2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₃

Average Molecular Weight

252.354

Monoisotopic Molecular Weight

252.172544633

IUPAC Name

6-(1,2-dihydroxypropan-2-yl)-4,4a-dimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

Traditional Name

6-(1,2-dihydroxypropan-2-yl)-4,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C=C2CCC(CC12C)C(C)(O)CO

InChI Identifier

InChI=1S/C15H24O3/c1-10-6-13(17)7-11-4-5-12(8-14(10,11)2)15(3,18)9-16/h7,10,12,16,18H,4-6,8-9H2,1-3H3

InChI Key

DJPISZPEZJGKKI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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: HMDB0037969)

Cellular substructure

Extracellular (HMDB: HMDB0037969)
Cytoplasm (HMDB: HMDB0037969)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037969)

Source

Endogenous

Endogenous (HMDB: HMDB0037969)

Plant

Plant (HMDB: HMDB0037969)

Animal

Animal (HMDB: HMDB0037969)

Exogenous

Food

Food (HMDB: HMDB0037969)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037969)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037969)

Cellular process

Cell signaling (HMDB: HMDB0037969)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037969)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037969)

Nutrient

Nutrient (HMDB: HMDB0037969)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037969)

Emulsifier (HMDB: HMDB0037969)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.1	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	2	ChemAxon
Refractivity	71.6 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]+	160.368	31661259
DarkChem	[M-H]-	159.391	31661259
DeepCCS	[M-2H]-	191.751	30932474
DeepCCS	[M+Na]+	167.316	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.7	32859911
AllCCS	[M+NH4]+	163.5	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Urodiolenone	CC1CC(=O)C=C2CCC(CC12C)C(C)(O)CO	3210.7	Standard polar	33892256
Urodiolenone	CC1CC(=O)C=C2CCC(CC12C)C(C)(O)CO	2031.5	Standard non polar	33892256
Urodiolenone	CC1CC(=O)C=C2CCC(CC12C)C(C)(O)CO	2256.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Urodiolenone,1TMS,isomer #1	CC1CC(=O)C=C2CCC(C(C)(CO)O[Si](C)(C)C)CC21C	2275.2	Semi standard non polar	33892256
Urodiolenone,1TMS,isomer #2	CC1CC(=O)C=C2CCC(C(C)(O)CO[Si](C)(C)C)CC21C	2263.3	Semi standard non polar	33892256
Urodiolenone,1TMS,isomer #3	CC1C=C(O[Si](C)(C)C)C=C2CCC(C(C)(O)CO)CC21C	2287.2	Semi standard non polar	33892256
Urodiolenone,2TMS,isomer #1	CC1CC(=O)C=C2CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC21C	2334.1	Semi standard non polar	33892256
Urodiolenone,2TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C=C2CCC(C(C)(CO)O[Si](C)(C)C)CC21C	2307.1	Semi standard non polar	33892256
Urodiolenone,2TMS,isomer #3	CC1C=C(O[Si](C)(C)C)C=C2CCC(C(C)(O)CO[Si](C)(C)C)CC21C	2293.8	Semi standard non polar	33892256
Urodiolenone,3TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C=C2CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC21C	2341.5	Semi standard non polar	33892256
Urodiolenone,3TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C=C2CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC21C	2368.8	Standard non polar	33892256
Urodiolenone,1TBDMS,isomer #1	CC1CC(=O)C=C2CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)CC21C	2542.8	Semi standard non polar	33892256
Urodiolenone,1TBDMS,isomer #2	CC1CC(=O)C=C2CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)CC21C	2532.7	Semi standard non polar	33892256
Urodiolenone,1TBDMS,isomer #3	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C(C)(O)CO)CC21C	2540.6	Semi standard non polar	33892256
Urodiolenone,2TBDMS,isomer #1	CC1CC(=O)C=C2CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC21C	2836.4	Semi standard non polar	33892256
Urodiolenone,2TBDMS,isomer #2	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)CC21C	2766.4	Semi standard non polar	33892256
Urodiolenone,2TBDMS,isomer #3	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)CC21C	2746.3	Semi standard non polar	33892256
Urodiolenone,3TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC21C	3013.5	Semi standard non polar	33892256
Urodiolenone,3TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC21C	3070.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Urodiolenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9b-2940000000-5f01c03ea7327efa7fbc	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Urodiolenone GC-MS (2 TMS) - 70eV, Positive	splash10-0f8i-4429000000-85620780f9c6eb1ba7f4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Urodiolenone 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 - Urodiolenone 10V, Positive-QTOF	splash10-0udi-0290000000-35ca57e1c7c2f30b702b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 20V, Positive-QTOF	splash10-0ftr-1970000000-4596020f8ab24e74c51d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 40V, Positive-QTOF	splash10-0uxr-9820000000-3e16bd6e06059df6598a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 10V, Negative-QTOF	splash10-0udi-0090000000-464d508fe8b58ad46d7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 20V, Negative-QTOF	splash10-0ufr-0490000000-2e65fa75813505327aeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 40V, Negative-QTOF	splash10-05di-5970000000-2ba29012a7d99eeec5fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 10V, Positive-QTOF	splash10-0uy0-0390000000-42786bf3933a964b9270	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 20V, Positive-QTOF	splash10-0q4r-3890000000-b77a0031a2aaff8abe61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 40V, Positive-QTOF	splash10-0a4l-9700000000-1f807ff5cd4fd6634f82	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 10V, Negative-QTOF	splash10-0udi-0090000000-0d8e0773b0aa36fd7521	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 20V, Negative-QTOF	splash10-0udi-0190000000-95fff1d7ed3ffe8493fc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urodiolenone 40V, Negative-QTOF	splash10-0002-0890000000-cc34d7be7245df6e9cff	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB017145

KNApSAcK ID

Not Available

Chemspider ID

35014495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15601437

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Urodiolenone (HMDB0037969)

MOL for HMDB0037969 (Urodiolenone)

3D MOL for HMDB0037969 (Urodiolenone)

3D SDF for HMDB0037969 (Urodiolenone)

3D-SDF for HMDB0037969 (Urodiolenone)

PDB for HMDB0037969 (Urodiolenone)

3D PDB for HMDB0037969 (Urodiolenone)

SMILES for HMDB0037969 (Urodiolenone)

INCHI for HMDB0037969 (Urodiolenone)

Structure for HMDB0037969 (Urodiolenone)

3D Structure for HMDB0037969 (Urodiolenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra