Showing metabocard for Geraniol (MMDBc0033644)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:57:12 UTC
Update Date2024-10-06 23:02:43 UTC
Metabolite IDMMDBc0033644
Metabolite Identification
Common NameGeraniol
Descriptionbeta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645 ). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923868d428>


  Mrv1652309272007292D          

 11 10  0  0  0  0            999 V2000
10001.371210000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.656010000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.940610000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.226310000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.511710000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.797410000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.511710001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.086410000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.799510000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.514710000.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.371210001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f923868d428>

HMDB0035155
     RDKit          3D
beta-Geraniol
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.4273   -0.7263    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    0.3839   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    1.7293   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.1493   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6901   -1.2092   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -1.2360    0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6576   -0.5481    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971   -0.5783    1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    0.1053   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3740    0.7727   -0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2229    2.1444   -1.1248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646   -1.0785    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -1.5283   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -0.4068    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    2.5259   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374    1.8450    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.8017   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.9463   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -1.6972   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -1.8538    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.8137    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.3062    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -1.0868    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.4454    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760   -1.2345    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347    0.1291   -1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253    0.2637   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061    0.6740    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3453    2.3877   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  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
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923868d428>


  Mrv1652309272007292D          

 11 10  0  0  0  0            999 V2000
10001.371210000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.656010000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.940610000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.226310000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.511710000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.797410000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.511710001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.086410000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.799510000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.514710000.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.371210001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033644

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCC\C(C)=C\CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+

> <INCHI_KEY>
GLZPCOQZEFWAFX-JXMROGBWSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.665728417645045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3,7-dimethylocta-2,6-dien-1-ol

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.5023832959999996

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.330024218725743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2170474067293595

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
51.1821

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geraniol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f923868d428>

HMDB0035155
     RDKit          3D
beta-Geraniol
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.4273   -0.7263    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513    0.3839   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1484    1.7293   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.1493   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6901   -1.2092   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -1.2360    0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6576   -0.5481    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6971   -0.5783    1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    0.1053   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3740    0.7727   -0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2229    2.1444   -1.1248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646   -1.0785    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -1.5283   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -0.4068    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    2.5259   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374    1.8450    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.8017   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041    0.9463   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -1.6972   -1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -1.8538    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.8137    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6922   -2.3062    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -1.0868    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.4454    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760   -1.2345    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3347    0.1291   -1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253    0.2637   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061    0.6740    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3453    2.3877   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  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
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
M  END
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PDB for #<Metabolite:0x00007f923868d428>

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    8669.2268667.514   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.8918666.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.5568667.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.2228666.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.8898667.514   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.5558666.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.8898669.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.5618666.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.8928667.514   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8673.2278666.747   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8669.2268669.055   0.000  0.00  0.00           C+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f923868d428>

COMPND    HMDB0035155
HETATM    1  C1  UNL     1       3.427  -0.726   0.128  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.551   0.384  -0.330  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.148   1.729  -0.501  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.250   0.149  -0.576  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.690  -1.209  -0.393  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.415  -1.236   0.575  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.658  -0.548   0.293  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.697  -0.578   1.403  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.033   0.105  -0.783  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.374   0.773  -0.908  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.223   2.144  -1.125  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.065  -1.078   1.106  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.405  -1.528  -0.662  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.495  -0.407   0.164  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.369   2.526  -0.396  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.937   1.845   0.286  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.552   1.802  -1.524  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.604   0.946  -0.901  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.463  -1.697  -1.369  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.520  -1.854   0.030  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.024  -0.814   1.557  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.692  -2.306   0.846  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.578  -1.087   0.965  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.896   0.445   1.777  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.376  -1.234   2.242  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.335   0.129  -1.622  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.925   0.264  -1.708  1.00  0.00           H  
HETATM   28  H17 UNL     1      -3.906   0.674   0.053  1.00  0.00           H  
HETATM   29  H18 UNL     1      -2.345   2.388  -0.709  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   27   28
CONECT   11   29
END
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SMILES for #<Metabolite:0x00007f923868d428>

CC(C)=CCC\C(C)=C\CO
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INCHI for #<Metabolite:0x00007f923868d428>

InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
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Synonyms
ValueSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(2E)-GeraniolChEBI
(e)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(e)-GeraniolChEBI
(e)-NerolChEBI
2-trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
3,7-Dimethyl-trans-2,6-octadien-1-olChEBI
Geranyl alcoholChEBI
LemonolChEBI
t-GeraniolChEBI
trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
trans-GeraniolChEBI
b-GeraniolGenerator
Β-geraniolGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-(e)-2,6-octadien-1-olHMDB
FEMA 2507HMDB
GeraniolHMDB
trans-2,6-Dimethyl-2,6-octadien-8-olHMDB
trans-3,7-Dimethy- octa-2,6-dien-1-olHMDB
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
NerolMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
Geraniol, (e)-isomerMeSH
(E)-3,7-Dimethyl-2,6-octadienolPhytoBank
trans-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-GeraniolPhytoBank
Molecular FormulaC10H18O
Average Mass154.253
Monoisotopic Mass154.1357652
IUPAC Name(2E)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namegeraniol
CAS Registry Number106-25-2
SMILES
CC(C)=CCC\C(C)=C\CO
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
InChI KeyGLZPCOQZEFWAFX-JXMROGBWSA-N