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Showing metabocard for (-)-beta-Pinene (HMDB0036559)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:42:57 UTC
Update Date2022-03-07 02:54:57 UTC
HMDB IDHMDB0036559
Secondary Accession Numbers
  • HMDB36559
Metabolite Identification
Common Name(-)-beta-Pinene
Description(-)-beta-Pinene, also known as terbenthene or (1S,5S)-b-pinene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (-)-beta-pinene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-beta-Pinene.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036559 ((-)-beta-Pinene)

  Mrv1652309272007312D          

 10 11  0  0  0  0            999 V2000
 9999.060510001.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.530810000.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0543 9999.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479110000.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.054210000.6502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.339710000.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3397 9999.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0542 9999.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7687 9999.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.768710000.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1  6  1  0  0  0  0
  6  2  1  0  0  0  0
 10  4  2  0  0  0  0
  5  3  1  1  0  0  0
  7  3  1  1  0  0  0
M  END
Download

3D MOL for HMDB0036559 ((-)-beta-Pinene)

HMDB0036559
     RDKit          3D
(-)-beta-Pinene
 26 27  0  0  0  0  0  0  0  0999 V2000
    1.6960    2.0862   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593    0.8581   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967   -0.3109   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -1.3086   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556   -1.3228    0.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4063   -0.8856    1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1583    0.5469    0.9182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0375   -0.0315    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348    0.6269   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -0.1187    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482    2.9341    0.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    2.2533   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7181   -0.7384   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.0193   -1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2489   -2.3151   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831   -1.0950   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -2.2429    0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -1.1583    2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.1535    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    1.2646    1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.7669   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318    0.0351   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.6219   -0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276    0.9330    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.6648    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671   -0.6004    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  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
  7  2  1  0
  8  5  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  1
  6 18  1  0
  6 19  1  0
  7 20  1  1
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0036559 ((-)-beta-Pinene)

  Mrv1652309272007312D          

 10 11  0  0  0  0            999 V2000
 9999.060510001.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.530810000.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0543 9999.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479110000.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.054210000.6502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.339710000.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3397 9999.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0542 9999.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7687 9999.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.768710000.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1  6  1  0  0  0  0
  6  2  1  0  0  0  0
 10  4  2  0  0  0  0
  5  3  1  1  0  0  0
  7  3  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0036559

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)[C@@H]2C[C@H]1C(=C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1

> <INCHI_KEY>
WTARULDDTDQWMU-IUCAKERBSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.234

> <EXACT_MASS>
136.125200512

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.13657364742479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
2.859595116666666

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-pinene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0036559 ((-)-beta-Pinene)

HMDB0036559
     RDKit          3D
(-)-beta-Pinene
 26 27  0  0  0  0  0  0  0  0999 V2000
    1.6960    2.0862   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593    0.8581   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967   -0.3109   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911   -1.3086   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556   -1.3228    0.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4063   -0.8856    1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1583    0.5469    0.9182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0375   -0.0315    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348    0.6269   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -0.1187    1.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482    2.9341    0.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075    2.2533   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7181   -0.7384   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473    0.0193   -1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2489   -2.3151   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831   -1.0950   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -2.2429    0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -1.1583    2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.1535    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    1.2646    1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.7669   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318    0.0351   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    1.6219   -0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276    0.9330    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.6648    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671   -0.6004    0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  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
  7  2  1  0
  8  5  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  1
  6 18  1  0
  6 19  1  0
  7 20  1  1
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0036559 ((-)-beta-Pinene)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.9138668.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.9248666.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.7688666.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.4288667.888   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.7688667.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.4348667.110   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8665.4348665.570   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.7688664.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.1028665.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.1028667.110   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    5    7                                                       
CONECT    4   10                                                            
CONECT    5    6   10    3                                                  
CONECT    6    5    7    1    2                                             
CONECT    7    6    8    3                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9    4                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0036559 ((-)-beta-Pinene)

COMPND    HMDB0036559
HETATM    1  C1  UNL     1       1.696   2.086  -0.253  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.259   0.858  -0.014  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.897  -0.311  -0.714  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.791  -1.309  -0.964  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.256  -1.323   0.101  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.406  -0.886   1.414  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.158   0.547   0.918  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.038  -0.032   0.176  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.335   0.627  -1.139  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.262  -0.119   1.019  1.00  0.00           C  
HETATM   11  H1  UNL     1       1.248   2.934   0.241  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.508   2.253  -0.948  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.718  -0.738  -0.101  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.347   0.019  -1.670  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.249  -2.315  -1.004  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.383  -1.095  -1.979  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.826  -2.243   0.191  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.142  -1.158   2.318  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.463  -1.154   1.491  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.063   1.265   1.700  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.458   0.767  -1.777  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.132   0.035  -1.632  1.00  0.00           H  
HETATM   23  H13 UNL     1      -1.773   1.622  -0.918  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.628   0.933   1.188  1.00  0.00           H  
HETATM   25  H15 UNL     1      -2.145  -0.665   1.962  1.00  0.00           H  
HETATM   26  H16 UNL     1      -3.067  -0.600   0.392  1.00  0.00           H  
CONECT    1    2    2   11   12
CONECT    2    3    7
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6    8   17
CONECT    6    7   18   19
CONECT    7    8   20
CONECT    8    9   10
CONECT    9   21   22   23
CONECT   10   24   25   26
END
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SMILES for HMDB0036559 ((-)-beta-Pinene)

CC1(C)[C@@H]2C[C@H]1C(=C)CC2
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INCHI for HMDB0036559 ((-)-beta-Pinene)

InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
Traditional Name(-)-β-pinene
CAS Registry Number18172-67-3
SMILES
CC1(C)[C@@H]2C[C@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1
InChI KeyWTARULDDTDQWMU-IUCAKERBSA-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
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-61 °CNot Available
Boiling Point165.00 to 167.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7.06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.239 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015463
KNApSAcK IDC00000806
Chemspider ID389794
KEGG Compound IDC06307
BioCyc IDCPD-4891
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440967
PDB IDNot Available
ChEBI ID28359
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ishida T, Asakawa Y, Takemoto T, Aratani T: Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J Pharm Sci. 1981 Apr;70(4):406-15. [PubMed:7229954 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.