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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:38:59 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035639

Secondary Accession Numbers

HMDB35639

Metabolite Identification

Common Name

Petasalbin

Description

Petasalbin 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 Petasalbin.

Structure

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

HMDB0035639
     RDKit          3D
Petasalbin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0638    0.6258    0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -0.2354   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -0.9731   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5715   -1.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -1.2975   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -0.4475   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    0.0306    0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212   -0.9864    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    0.3816    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.8922   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    0.1057    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979    1.4230    1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.8428    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3198   -0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553   -0.4288   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -0.3038   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.6596   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.6996    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263    0.3978    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268    0.4370    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -1.0080   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    0.9086    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.3978    2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944    2.2061   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512    2.0329   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    2.4796    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.3326    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    1.1436    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    2.0995    0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    1.9088    2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302   -0.7853    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604   -1.8839    0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -0.8794   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2867    0.7705   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.4298   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    0.3072   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.3113   -1.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -2.0530   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -2.3254   -0.3714 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  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6  2  1  0
 16  9  1  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

  Mrv0541 05061308372D          

 17 19  0  0  0  0            999 V2000
    4.6119   -2.2771    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
    2.1434   -2.0625    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035639

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-8-17-12-7-11-6-4-5-10(2)15(11,3)14(16)13(9)12/h8,10-11,14,16H,4-7H2,1-3H3

> <INCHI_KEY>
ANKFPIBCTISOBX-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.26934201354274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.3548728246666677

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.607063852011933

> <JCHEM_PKA_STRONGEST_BASIC>
-2.077224639081559

> <JCHEM_POLAR_SURFACE_AREA>
33.370000000000005

> <JCHEM_REFRACTIVITY>
68.00850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035639
     RDKit          3D
Petasalbin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0638    0.6258    0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -0.2354   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -0.9731   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5715   -1.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -1.2975   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -0.4475   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    0.0306    0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212   -0.9864    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    0.3816    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.8922   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    0.1057    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979    1.4230    1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.8428    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3198   -0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553   -0.4288   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -0.3038   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.6596   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.6996    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263    0.3978    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268    0.4370    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -1.0080   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    0.9086    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.3978    2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944    2.2061   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512    2.0329   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    2.4796    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.3326    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    1.1436    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    2.0995    0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    1.9088    2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302   -0.7853    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604   -1.8839    0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -0.8794   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2867    0.7705   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.4298   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    0.3072   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.3113   -1.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -2.0530   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -2.3254   -0.3714 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  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6  2  1  0
 16  9  1  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 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       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7   11   12                                                       
CONECT    8    9   17                                                       
CONECT    9    1    8   13                                                  
CONECT   10    2    5   15                                                  
CONECT   11    6    7   15                                                  
CONECT   12    7   13   17                                                  
CONECT   13    9   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    3   10   11   14                                             
CONECT   16   14                                                            
CONECT   17    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0035639
HETATM    1  C1  UNL     1       4.064   0.626   0.861  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.290  -0.235  -0.078  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.722  -0.973  -1.152  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.701  -1.571  -1.685  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.591  -1.297  -1.053  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.925  -0.447  -0.020  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.873   0.031   0.870  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.621  -0.986   1.806  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.430   0.382   0.185  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.353   1.892  -0.091  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.530   0.106   1.180  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.198   1.423   1.603  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.581  -0.843   0.664  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.054  -0.320  -0.662  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.955  -0.429  -1.648  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.574  -0.304  -1.115  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.154  -1.660  -1.175  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.845   1.700   0.645  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.126   0.398   0.876  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.627   0.437   1.881  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.779  -1.008  -1.458  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.227   0.909   1.455  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.489  -1.398   2.021  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.094   2.206  -0.839  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.651   2.033  -0.590  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.326   2.480   0.824  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.157  -0.333   2.133  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.186   1.144   2.012  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.350   2.099   0.765  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.555   1.909   2.349  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.430  -0.785   1.403  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.260  -1.884   0.658  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.943  -0.879  -1.001  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.287   0.770  -0.508  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.042  -1.430  -2.159  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.173   0.307  -2.477  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.000   0.311  -1.878  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.066  -2.053  -2.194  1.00  0.00           H  
HETATM   39  H22 UNL     1      -0.140  -2.325  -0.371  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    6
CONECT    3    4   21
CONECT    4    5
CONECT    5    6    6   17
CONECT    6    7
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   11   16
CONECT   10   24   25   26
CONECT   11   12   13   27
CONECT   12   28   29   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   37
CONECT   17   38   39
END

HMDB0035639
     RDKit          3D
Petasalbin
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0638    0.6258    0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -0.2354   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -0.9731   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5715   -1.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -1.2975   -1.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -0.4475   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    0.0306    0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212   -0.9864    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    0.3816    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    1.8922   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    0.1057    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979    1.4230    1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -0.8428    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3198   -0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553   -0.4288   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739   -0.3038   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.6596   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8449    1.6996    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263    0.3978    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268    0.4370    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -1.0080   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    0.9086    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.3978    2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0944    2.2061   -0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512    2.0329   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    2.4796    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -0.3326    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    1.1436    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    2.0995    0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    1.9088    2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302   -0.7853    1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604   -1.8839    0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -0.8794   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2867    0.7705   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.4298   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1727    0.3072   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.3113   -1.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -2.0530   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1402   -2.3254   -0.3714 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  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6  2  1  0
 16  9  1  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxyfuranoeremophilane	HMDB
Ligularol	HMDB
Methyl 2-oxoheptanoate	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

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

Traditional Name

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

CAS Registry Number

4176-11-8

SMILES

CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3

InChI Identifier

InChI=1S/C15H22O2/c1-9-8-17-12-7-11-6-4-5-10(2)15(11,3)14(16)13(9)12/h8,10-11,14,16H,4-7H2,1-3H3

InChI Key

ANKFPIBCTISOBX-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
Heteroaromatic compound
Furan
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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: HMDB0035639)

Source

Endogenous

Endogenous (HMDB: HMDB0035639)

Plant

Plant (HMDB: HMDB0035639)

Animal

Animal (HMDB: HMDB0035639)

Exogenous

Food

Food (HMDB: HMDB0035639)

Tea

Vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0035639)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035639)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035639)

Lipid metabolism pathway (HMDB: HMDB0035639)

Cellular process

Cell signaling (HMDB: HMDB0035639)

Biochemical process

Lipid transport (HMDB: HMDB0035639)

Role

Biological role

Energy source (HMDB: HMDB0035639)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	81 - 82 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22.86 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	0.034 g/L	ALOGPS
logP	3.56	ALOGPS
logP	3.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.01 m³·mol⁻¹	ChemAxon
Polarizability	27.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.949	31661259
DarkChem	[M-H]-	151.435	31661259
DeepCCS	[M-2H]-	190.453	30932474
DeepCCS	[M+Na]+	165.878	30932474
AllCCS	[M+H]+	155.5	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Petasalbin	CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3	2580.6	Standard polar	33892256
Petasalbin	CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3	1761.6	Standard non polar	33892256
Petasalbin	CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3	1869.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Petasalbin,1TMS,isomer #1	CC1=COC2=C1C(O[Si](C)(C)C)C1(C)C(C)CCCC1C2	1913.1	Semi standard non polar	33892256
Petasalbin,1TBDMS,isomer #1	CC1=COC2=C1C(O[Si](C)(C)C(C)(C)C)C1(C)C(C)CCCC1C2	2186.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Petasalbin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-7970000000-8d46cf4a428bd09f4e8b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasalbin GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4190000000-24de5045562533db2962	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasalbin 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 - Petasalbin 10V, Positive-QTOF	splash10-014r-0190000000-b1c2852032e9fd93747d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 20V, Positive-QTOF	splash10-014r-3890000000-0199194ea2f57637c1da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 40V, Positive-QTOF	splash10-0gbc-9510000000-1d8d3c10fd5cbb3c18ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 10V, Negative-QTOF	splash10-001i-0090000000-d0eb8236bea45bdfa1a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 20V, Negative-QTOF	splash10-001i-0190000000-b576e1ad8f95a2be5244	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 40V, Negative-QTOF	splash10-0g4u-1930000000-7d8c9b3df723cba8fdc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 20V, Negative-QTOF	splash10-001i-0090000000-a7e47711b65406a80f2f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 40V, Negative-QTOF	splash10-0089-0890000000-dad4d329533992f7de0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 10V, Positive-QTOF	splash10-000i-0090000000-cebf8e78d653585cc1d2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 20V, Positive-QTOF	splash10-00kr-2890000000-ffdf73a771ad53fcc911	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasalbin 40V, Positive-QTOF	splash10-0a4j-9700000000-d05e7c857acba76992b9	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014349

KNApSAcK ID

C00017368

Chemspider ID

434155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

495921

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1850791

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 Petasalbin (HMDB0035639)

MOL for HMDB0035639 (Petasalbin)

3D MOL for HMDB0035639 (Petasalbin)

3D SDF for HMDB0035639 (Petasalbin)

3D-SDF for HMDB0035639 (Petasalbin)

PDB for HMDB0035639 (Petasalbin)

3D PDB for HMDB0035639 (Petasalbin)

SMILES for HMDB0035639 (Petasalbin)

INCHI for HMDB0035639 (Petasalbin)

Structure for HMDB0035639 (Petasalbin)

3D Structure for HMDB0035639 (Petasalbin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra