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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:56:26 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033227

Secondary Accession Numbers

HMDB33227

Metabolite Identification

Common Name

Curcolonol

Description

Curcolonol 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 Curcolonol.

Structure

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

HMDB0033227
     RDKit          3D
Curcolonol
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.8156    2.1114   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.7324   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.4342   -0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.4255   -0.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -1.0198   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.3308   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    1.0556   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    2.2745   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438    0.3071    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0082    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4746    2.4431    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9979    1.0946   -1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399    0.2996    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.9437    1.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4481   -1.8417    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -2.7443    1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150   -1.1031   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.1390   -1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.8599   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    2.4609    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    2.1090   -1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    2.7533   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1324   -0.5003   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.2775    1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674    3.1452   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.7548    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423    2.5129    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    1.1005   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.9950    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280    0.0798    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -0.7032    2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2070   -1.5200    1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -2.4472    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -3.4492    1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.3727   -2.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1285   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -1.2063   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8602   -2.6983   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -2.3090    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  6  2  1  0
 17  9  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061307002D          

 19 21  0  0  0  0            999 V2000
    3.1830    3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    3.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    3.1070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 15  1  0  0  0  0
 19  7  1  0  0  0  0
 19  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033227

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1C(=O)C1C(C)(O)CCC(O)C1(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-7-19-9-6-14(2)10(16)4-5-15(3,18)13(14)12(17)11(8)9/h7,10,13,16,18H,4-6H2,1-3H3

> <INCHI_KEY>
QXEXMTIZXNCRJO-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.326320281127686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.0733036979999997

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.321369036114056

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.703451251062464

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9463960946321377

> <JCHEM_POLAR_SURFACE_AREA>
70.67

> <JCHEM_REFRACTIVITY>
70.58

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033227
     RDKit          3D
Curcolonol
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.8156    2.1114   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.7324   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.4342   -0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.4255   -0.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -1.0198   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.3308   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    1.0556   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    2.2745   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438    0.3071    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0082    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4746    2.4431    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9979    1.0946   -1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399    0.2996    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.9437    1.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4481   -1.8417    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -2.7443    1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150   -1.1031   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.1390   -1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.8599   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    2.4609    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    2.1090   -1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    2.7533   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1324   -0.5003   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.2775    1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674    3.1452   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.7548    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423    2.5129    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    1.1005   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.9950    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280    0.0798    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -0.7032    2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2070   -1.5200    1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -2.4472    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -3.4492    1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.3727   -2.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1285   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -1.2063   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8602   -2.6983   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -2.3090    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  6  2  1  0
 17  9  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  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       5.942   5.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.990   5.800   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.466   4.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.990   5.800   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.466   1.834   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5   10                                                       
CONECT    5    4   15                                                       
CONECT    6    9   14                                                       
CONECT    7    8   19                                                       
CONECT    8    1    7   11                                                  
CONECT    9    6   11   19                                                  
CONECT   10    4   14   16                                                  
CONECT   11    8    9   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14    2    6   10   13                                             
CONECT   15    3    5   13   18                                             
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
CONECT   19    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033227
HETATM    1  C1  UNL     1       3.816   2.111  -0.929  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.341   0.732  -0.734  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.063  -0.434  -0.826  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.270  -1.426  -0.583  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.053  -1.020  -0.330  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.046   0.331  -0.413  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.804   1.056  -0.176  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.786   2.275  -0.461  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.344   0.307   0.383  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.654   1.008   0.135  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.475   2.443   0.650  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.998   1.095  -1.193  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.740   0.300   0.874  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.292  -0.944   1.566  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.448  -1.842   0.724  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.809  -2.744   1.597  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.415  -1.103  -0.101  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.910  -1.139  -1.541  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.868  -1.860  -0.007  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.219   2.461   0.048  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.674   2.109  -1.635  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.007   2.753  -1.314  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.132  -0.500  -1.066  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.205   0.278   1.492  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.367   3.145  -0.202  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.391   2.755   1.221  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.642   2.513   1.374  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.976   1.100  -1.344  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.134   0.995   1.653  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.628   0.080   0.219  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.776  -0.703   2.541  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.207  -1.520   1.863  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.144  -2.447   0.076  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.415  -3.449   1.902  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.464  -0.373  -2.171  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.547  -2.129  -1.949  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.016  -1.206  -1.597  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.860  -2.698  -0.735  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.060  -2.309   0.990  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    6
CONECT    3    4   23
CONECT    4    5
CONECT    5    6    6   19
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   17   24
CONECT   10   11   12   13
CONECT   11   25   26   27
CONECT   12   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   17   33
CONECT   16   34
CONECT   17   18   19
CONECT   18   35   36   37
CONECT   19   38   39
END

HMDB0033227
     RDKit          3D
Curcolonol
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.8156    2.1114   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.7324   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.4342   -0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698   -1.4255   -0.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528   -1.0198   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.3308   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    1.0556   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    2.2745   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438    0.3071    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.0082    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4746    2.4431    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9979    1.0946   -1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399    0.2996    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.9437    1.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4481   -1.8417    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -2.7443    1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150   -1.1031   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099   -1.1390   -1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -1.8599   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    2.4609    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    2.1090   -1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    2.7533   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1324   -0.5003   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.2775    1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674    3.1452   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.7548    1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423    2.5129    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    1.1005   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    0.9950    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280    0.0798    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -0.7032    2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2070   -1.5200    1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -2.4472    0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153   -3.4492    1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641   -0.3727   -2.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1285   -1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -1.2063   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8602   -2.6983   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -2.3090    0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  6  2  1  0
 17  9  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

217817-09-9

SMILES

CC1=COC2=C1C(=O)C1C(C)(O)CCC(O)C1(C)C2

InChI Identifier

InChI=1S/C15H20O4/c1-8-7-19-9-6-14(2)10(16)4-5-15(3,18)13(14)12(17)11(8)9/h7,10,13,16,18H,4-6H2,1-3H3

InChI Key

QXEXMTIZXNCRJO-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

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Aryl alkyl ketone
Cyclic alcohol
Furan
Tertiary alcohol
Heteroaromatic compound
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033227)

Source

Endogenous

Endogenous (HMDB: HMDB0033227)

Animal

Animal (HMDB: HMDB0033227)

Exogenous

Food

Food (HMDB: HMDB0033227)

Exogenous (HMDB: HMDB0033227)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033227)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033227)

Lipid metabolism pathway (HMDB: HMDB0033227)

Cellular process

Cell signaling (HMDB: HMDB0033227)

Biochemical process

Lipid transport (HMDB: HMDB0033227)

Role

Biological role

Energy source (HMDB: HMDB0033227)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	306.6 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	0.51 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.07	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.7	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.58 m³·mol⁻¹	ChemAxon
Polarizability	28.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.859	31661259
DarkChem	[M-H]-	157.744	31661259
DeepCCS	[M+H]+	162.176	30932474
DeepCCS	[M-H]-	159.818	30932474
DeepCCS	[M-2H]-	193.156	30932474
DeepCCS	[M+Na]+	168.376	30932474
AllCCS	[M+H]+	160.8	32859911
AllCCS	[M+H-H2O]+	157.2	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.47 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1597 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1609.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	408.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	500.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	866.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	376.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1256.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	296.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	262.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	69.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcolonol	CC1=COC2=C1C(=O)C1C(C)(O)CCC(O)C1(C)C2	3023.3	Standard polar	33892256
Curcolonol	CC1=COC2=C1C(=O)C1C(C)(O)CCC(O)C1(C)C2	2037.9	Standard non polar	33892256
Curcolonol	CC1=COC2=C1C(=O)C1C(C)(O)CCC(O)C1(C)C2	2233.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcolonol,1TMS,isomer #1	CC1=COC2=C1C(=O)C1C(C)(O[Si](C)(C)C)CCC(O)C1(C)C2	2329.2	Semi standard non polar	33892256
Curcolonol,1TMS,isomer #2	CC1=COC2=C1C(=O)C1C(C)(O)CCC(O[Si](C)(C)C)C1(C)C2	2341.4	Semi standard non polar	33892256
Curcolonol,2TMS,isomer #1	CC1=COC2=C1C(=O)C1C(C)(O[Si](C)(C)C)CCC(O[Si](C)(C)C)C1(C)C2	2342.8	Semi standard non polar	33892256
Curcolonol,1TBDMS,isomer #1	CC1=COC2=C1C(=O)C1C(C)(O[Si](C)(C)C(C)(C)C)CCC(O)C1(C)C2	2569.9	Semi standard non polar	33892256
Curcolonol,1TBDMS,isomer #2	CC1=COC2=C1C(=O)C1C(C)(O)CCC(O[Si](C)(C)C(C)(C)C)C1(C)C2	2579.4	Semi standard non polar	33892256
Curcolonol,2TBDMS,isomer #1	CC1=COC2=C1C(=O)C1C(C)(O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)C1(C)C2	2786.4	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 - Curcolonol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i4-7490000000-5b71dc48a64601674306	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcolonol GC-MS (2 TMS) - 70eV, Positive	splash10-004l-9487000000-c2ebd20b9f5d8a63fe6e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcolonol 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 - Curcolonol 10V, Positive-QTOF	splash10-0002-0090000000-4dd573e03be070fbcad4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 20V, Positive-QTOF	splash10-002b-0290000000-be79844a4c4a6946252f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 40V, Positive-QTOF	splash10-01sj-4960000000-718b1a3118d6d3b316b5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 10V, Negative-QTOF	splash10-03di-0090000000-f23fc451f13b35e45bac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 20V, Negative-QTOF	splash10-03dj-0190000000-e90faf9f6c19f72b548a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 40V, Negative-QTOF	splash10-03dj-4890000000-b755600a94eb22a92add	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 10V, Positive-QTOF	splash10-014i-0090000000-d0d395afd805094f8e89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 20V, Positive-QTOF	splash10-014j-1590000000-b2ada2acce8dd6b19579	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 40V, Positive-QTOF	splash10-02ta-7910000000-d64c13de3c23b55aa17c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 20V, Negative-QTOF	splash10-03di-1490000000-eb5b26798d95712c36ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcolonol 40V, Negative-QTOF	splash10-03di-3920000000-f002c9cd79e1fc2df87f	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

FDB011242

KNApSAcK ID

C00055323

Chemspider ID

22370261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45359845

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833991

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 ]
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Showing metabocard for Curcolonol (HMDB0033227)

MOL for HMDB0033227 (Curcolonol)

3D MOL for HMDB0033227 (Curcolonol)

3D SDF for HMDB0033227 (Curcolonol)

3D-SDF for HMDB0033227 (Curcolonol)

PDB for HMDB0033227 (Curcolonol)

3D PDB for HMDB0033227 (Curcolonol)

SMILES for HMDB0033227 (Curcolonol)

INCHI for HMDB0033227 (Curcolonol)

Structure for HMDB0033227 (Curcolonol)

3D Structure for HMDB0033227 (Curcolonol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra