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Showing metabocard for Alpha-Pinene-oxide (HMDB0003667)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 02:52:10 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003667
Secondary Accession Numbers
  • HMDB0006291
  • HMDB03667
  • HMDB06291
Metabolite Identification
Common NameAlpha-Pinene-oxide
DescriptionAlpha-pinene oxide is cheap monoterpene, which is important compound for the fragnance industry. Biocatalytic method is used to convert monoterpenes into terpenoids. The biotransformation of alpha-pinene oxide using resting cells of Pseudomonas fluorescens NCIMB 11671 produces isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. However, this biotransformation has technical problems including the following: alpha-pinene oxide undergoes autoxidation in water and light; it is hydrophobic and relatively toxic to the biocatalyst; and it suffers from product inhibition. the influence of other terpene byproducts on the flux of alpha-pinene oxide was investigated and found to decrease the flux into the organic phase by up to 10%. (PMID: 16321051 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003667 (Alpha-Pinene-oxide)

  Mrv0541 02231219472D          

 11 13  0  0  0  0            999 V2000
   11.0503  -11.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076  -11.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4781   -8.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6553   -8.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5939  -10.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3042   -8.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9802  -10.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6251  -10.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7990   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0503   -9.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8559  -10.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for HMDB0003667 (Alpha-Pinene-oxide)

HMDB0003667
     RDKit          3D
Alpha-Pinene-oxide
 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.2804    0.7369    0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    0.2520    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106    0.6533   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -1.2092    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.8348   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.0284   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.9189    0.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.2496    0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    1.3489   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.5372    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1753   -0.7169    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -0.0418    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    1.0235    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766    1.6118    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786    1.7745   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022    0.4158   -1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    0.2004   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026   -1.8129    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844   -1.9000   -1.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -2.8696   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -1.0957   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424    2.3283    0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2440    1.5186   -1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    1.1308   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.4286    1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9407   -0.5264    2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220   -1.2556    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
 11  4  1  0
  8  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for HMDB0003667 (Alpha-Pinene-oxide)

  Mrv0541 02231219472D          

 11 13  0  0  0  0            999 V2000
   11.0503  -11.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076  -11.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4781   -8.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6553   -8.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5939  -10.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3042   -8.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9802  -10.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6251  -10.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7990   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0503   -9.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8559  -10.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003667

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12OC1CC1CC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3

> <INCHI_KEY>
NQFUSWIGRKFAHK-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.87941079230503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
1.9788336679999998

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226627812474885

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
43.4058

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-pinene oxide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0003667 (Alpha-Pinene-oxide)

HMDB0003667
     RDKit          3D
Alpha-Pinene-oxide
 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.2804    0.7369    0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    0.2520    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106    0.6533   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -1.2092    0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -1.8348   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.0284   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -0.9189    0.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.2496    0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    1.3489   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.5372    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1753   -0.7169    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -0.0418    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    1.0235    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0766    1.6118    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786    1.7745   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022    0.4158   -1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    0.2004   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026   -1.8129    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844   -1.9000   -1.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -2.8696   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -1.0957   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424    2.3283    0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2440    1.5186   -1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    1.1308   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.4286    1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9407   -0.5264    2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220   -1.2556    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
 11  4  1  0
  8  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
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PDB for HMDB0003667 (Alpha-Pinene-oxide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      20.627 -21.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      22.788 -20.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.292 -15.116   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.757 -16.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.642 -20.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.968 -16.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.496 -19.819   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.567 -18.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.891 -17.559   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.627 -18.572   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.864 -19.073   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    6                                                            
CONECT    5    1    2    7    8                                             
CONECT    6    3    4    8    9                                             
CONECT    7    1    5   10                                                  
CONECT    8    5    6   11                                                  
CONECT    9    6   10   11                                                  
CONECT   10    7    9                                                       
CONECT   11    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   26    0
END
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3D PDB for HMDB0003667 (Alpha-Pinene-oxide)

COMPND    HMDB0003667
HETATM    1  C1  UNL     1      -2.280   0.737   0.736  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.052   0.252   0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.011   0.653  -1.421  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.824  -1.209   0.313  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.208  -1.835  -0.576  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.467  -1.028  -0.610  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.226  -0.919   0.549  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.454   0.250   0.071  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.369   1.349  -0.378  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.201   0.537   0.811  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.175  -0.717   1.615  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.724  -0.042   1.401  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.102   1.023   0.034  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.077   1.612   1.387  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.879   1.775  -1.447  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.002   0.416  -1.868  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.181   0.200  -1.969  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.703  -1.813   0.533  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.184  -1.900  -1.611  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.376  -2.870  -0.208  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.115  -1.096  -1.532  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.142   2.328   0.118  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.244   1.519  -1.470  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.442   1.131  -0.221  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.168   1.429   1.443  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.941  -0.526   2.378  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.722  -1.256   1.912  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   10
CONECT    3   15   16   17
CONECT    4    5   11   18
CONECT    5    6   19   20
CONECT    6    7    8   21
CONECT    7    8
CONECT    8    9   10
CONECT    9   22   23   24
CONECT   10   11   25
CONECT   11   26   27
END
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SMILES for HMDB0003667 (Alpha-Pinene-oxide)

CC12OC1CC1CC2C1(C)C
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INCHI for HMDB0003667 (Alpha-Pinene-oxide)

InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,7,7-Trimethyl-3-oxatricyclo[4.1.1.0(2,4)]octaneChEBI
2-Pinene oxideChEBI
alpha-Pinene epoxideChEBI
a-Pinene epoxideGenerator
Α-pinene epoxideGenerator
a-Pinene-oxideGenerator
Α-pinene-oxideGenerator
alpha-Pinane oxideMeSH
2,3-Epoxy-pinaneHMDB
2,3-EpoxypinaneHMDB
alpha-Pinene 2,3-oxideHMDB
alpha-Pinene oxideHMDB
Pinene oxideHMDB
alpha-Pinene-oxideChEBI
a-Pinene oxideGenerator, HMDB
Α-pinene oxideGenerator, HMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane
Traditional Nameα-pinene oxide
CAS Registry Number1686-14-2
SMILES
CC12OC1CC1CC2C1(C)C
InChI Identifier
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3
InChI KeyNQFUSWIGRKFAHK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Oxepane
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.01Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023213
KNApSAcK IDNot Available
Chemspider ID82629
KEGG Compound IDC02759
BioCyc IDALPHA-PINENE-OXIDE
BiGG ID40512
Wikipedia LinkNot Available
METLIN ID6974
PubChem Compound91508
PDB IDNot Available
ChEBI ID29060
Food Biomarker OntologyNot Available
VMH IDAPNNOX
MarkerDB IDNot Available
Good Scents IDrw1218571
References
Synthesis ReferenceDing, Zongbiao; Lu, Wencong; Wang, Quanrui; Tao, Fenggang; Hu, Jianliang; Yang, Yuqing. Process for the preparation of a-epoxypinane with Na percarbonate as reagent. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. [PubMed:12576684 ]
  2. Boontawan A, Stuckey DC: Mass transfer of terpenes through a silicone rubber membrane in a liquid-liquid contacting system. Biotechnol Prog. 2005 Nov-Dec;21(6):1680-7. [PubMed:16321051 ]