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Showing metabocard for Geraniol (HMDB0005812)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 23:21:34 UTC
Update Date2023-02-21 17:17:08 UTC
HMDB IDHMDB0005812
Secondary Accession Numbers
  • HMDB0005804
  • HMDB05804
  • HMDB05812
Metabolite Identification
Common NameGeraniol
DescriptionGeraniol, also known as beta-Geraniol, (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. In plants, 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. It is found 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. 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. An alternate application has been found in the use of insect repellents or deterrants. Though it may repel mosquitoes, flies, lice, cockroaches, ants, and ticks, it is also produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403). Extensive testing by Dr. Jerry Butler at the University of Florida has shown geraniol to be one of nature's most effective insect repellents (PMID:20836800 ).
Structure
Data?1676999828
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005812 (Geraniol)


  Mrv1652309272007362D          

 11 10  0  0  0  0            999 V2000
    5.3735   -8.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0879   -8.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8023   -8.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169   -8.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -8.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -6.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299   -6.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9444   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300   -6.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  8  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0005812 (Geraniol)

HMDB0005812
     RDKit          3D
Geraniol
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.8661   -1.4581    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -0.5100    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433    0.9377    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5260   -0.9443    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765   -0.0281    0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230   -0.1828   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    0.7139   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    2.2254   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    0.2786   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -1.1495   -0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610   -1.3349   -1.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4581   -1.0816   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5327   -2.4761   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -1.4623    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326    1.4211    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537    1.1268    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    1.4972   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372   -2.0076    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -0.2367    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7443    1.0092    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -1.2263   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    0.1425   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    2.5411    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    2.7021   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393    2.4480   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107    1.0513    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -1.8695   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373   -1.4010    0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333   -0.7262   -1.0828 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 HMDB0005812 (Geraniol)


  Mrv1652309272007362D          

 11 10  0  0  0  0            999 V2000
    5.3735   -8.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0879   -8.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8023   -8.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5169   -8.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -8.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -6.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299   -6.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9444   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300   -6.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  8  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005812

> <DATABASE_NAME>
hmdb

> <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-YFHOEESVSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.29002922323904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-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>
nerol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005812 (Geraniol)

HMDB0005812
     RDKit          3D
Geraniol
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.8661   -1.4581    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -0.5100    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433    0.9377    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5260   -0.9443    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765   -0.0281    0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230   -0.1828   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    0.7139   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    2.2254   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0053    0.2786   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -1.1495   -0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610   -1.3349   -1.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4581   -1.0816   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5327   -2.4761   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -1.4623    1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326    1.4211    1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537    1.1268    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    1.4972   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372   -2.0076    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -0.2367    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7443    1.0092    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -1.2263   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513    0.1425   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4931    2.5411    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    2.7021   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393    2.4480   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107    1.0513    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -1.8695   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373   -1.4010    0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333   -0.7262   -1.0828 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 HMDB0005812 (Geraniol)

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      10.031 -15.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.364 -15.994   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.698 -15.224   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.031 -13.684   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.032 -15.994   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.697 -15.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.697 -12.914   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.029 -11.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.363 -13.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.029 -12.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.696 -13.684   0.000  0.00  0.00           C+0
CONECT    1    2    4    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3                                                            
CONECT    6    1                                                            
CONECT    7    4    9                                                       
CONECT    8   10                                                            
CONECT    9    7   10                                                       
CONECT   10    9    8   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0005812 (Geraniol)

COMPND    HMDB0005812
HETATM    1  C1  UNL     1       3.866  -1.458   0.211  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.756  -0.510   0.420  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.043   0.938   0.487  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.526  -0.944   0.546  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.376  -0.028   0.757  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.623  -0.183  -0.379  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.780   0.714  -0.201  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.556   2.225  -0.154  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.005   0.279  -0.081  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.370  -1.149  -0.108  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.261  -1.335  -1.201  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.458  -1.082  -0.662  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.533  -2.476  -0.041  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.583  -1.462   1.073  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.633   1.421   1.404  1.00  0.00           H  
HETATM   16  H5  UNL     1       4.154   1.127   0.542  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.620   1.497  -0.386  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.337  -2.008   0.493  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.122  -0.237   1.727  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.744   1.009   0.734  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.863  -1.226  -0.590  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.051   0.143  -1.320  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.493   2.541   0.897  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.404   2.702  -0.686  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.639   2.448  -0.699  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.811   1.051   0.049  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.579  -1.869  -0.220  1.00  0.00           H  
HETATM   28  H17 UNL     1      -4.037  -1.401   0.786  1.00  0.00           H  
HETATM   29  H18 UNL     1      -5.033  -0.726  -1.083  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 HMDB0005812 (Geraniol)

CC(C)=CCC\C(C)=C/CO
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INCHI for HMDB0005812 (Geraniol)

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
(2Z)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(Z)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(Z)-3,7-Dimethylocta-2,6-dien-1-olChEBI
(Z)-GeraniolChEBI
2-cis-3,7-Dimethyl-2,6-octadien-1-olChEBI
cis-3,7-Dimethyl-2,6-octadien-1-olChEBI
cis-GeraniolChEBI
Neryl alcoholChEBI
Geraniol, (e)-isomerMeSH
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
(2E)3,7-Dimethyl-2,6-octadien-1-olHMDB
(2Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
(cis)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-2,6-octadien-1-olHMDB
(e)3,7-Dimethyl-octadien-1-olHMDB
(Z)3,7-Dimethyl-2,6-octadien-1-olHMDB
2,6-Dimethyl-trans-2,6-octadien-8-olHMDB
2-trans-3,7-Dimethyl-2,6-octadien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-2,6-octadien-1-olHMDB
3,7-Dimethyl-octane-1-ol tetrahydro derivativeHMDB
3,7-Dimethyl-trans-2, 6-octadien-1-olHMDB
3,7-Dimethylocta-2,6-dien-1-olHMDB
beta-GeraniolHMDB
Geraniol (natural)HMDB
Geraniol alcoholHMDB
Geranyl alcoholHMDB
GuaniolHMDB
LemonolHMDB
NerolHMDB
Nerol (natural)HMDB
Nerolidyl diphosphateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-olHMDB
trans-GeraniolHMDB
VernolHMDB
GeraniolMeSH
(Z)-3,7-Dimethyl-2,6-octadienolPhytoBank
(Z)-3,7-Dimethyloct-2,6-diene-1-olPhytoBank
(Z)-NerolPhytoBank
3,7-Dimethyl-cis-2,6-octadien-1-olPhytoBank
cis-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-NerolPhytoBank
β-NerolPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namenerol
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-YFHOEESVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -15 °CNot Available
Boiling Point103.00 to 105.00 °C. @ 9.00 mm HgThe Good Scents Company Information System
Water Solubility0.53 mg/mL at 25 °CNot Available
LogP3.47GRIFFIN,S ET AL. (1999)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.57231661259
DarkChem[M-H]-132.30831661259
DeepCCS[M+H]+140.66730932474
DeepCCS[M-H]-137.87530932474
DeepCCS[M-2H]-174.44630932474
DeepCCS[M+Na]+149.85630932474
AllCCS[M+H]+136.732859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+140.532859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-137.732859911
AllCCS[M+Na-2H]-139.732859911
AllCCS[M+HCOO]-142.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.5.97 minutes32390414
Predicted by Siyang on May 30, 202212.6157 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.37 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid25.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2132.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid343.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid147.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid197.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid78.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid414.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid488.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)64.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1060.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid424.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid919.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid350.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid328.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate310.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA376.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water10.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GeraniolCC(C)=CCC\C(C)=C/CO1835.5Standard polar33892256
GeraniolCC(C)=CCC\C(C)=C/CO1226.4Standard non polar33892256
GeraniolCC(C)=CCC\C(C)=C/CO1249.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Geraniol,1TMS,isomer #1CC(C)=CCC/C(C)=C\CO[Si](C)(C)C1341.9Semi standard non polar33892256
Geraniol,1TBDMS,isomer #1CC(C)=CCC/C(C)=C\CO[Si](C)(C)C(C)(C)C1559.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-8132ea67e057a3dd9c802017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9100000000-a5bdece739d0cb5bf6292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-015c-9200000000-eea073073c86ea4d9a382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-0006-9000000000-0625da1bcd5a7d1938a62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-41e0055b618413366b812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-8132ea67e057a3dd9c802018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9100000000-a5bdece739d0cb5bf6292018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-015c-9200000000-eea073073c86ea4d9a382018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-0006-9000000000-0625da1bcd5a7d1938a62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-41e0055b618413366b812018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Geraniol GC-EI-Q (Non-derivatized)splash10-014l-9000000000-2ab93357dd27a7c07eb72020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Geraniol GC-MS (Non-derivatized) - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Geraniol GC-MS (1 TMS) - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Geraniol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001r-9600000000-69c0de28e07b8b530c9a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9100000000-0ee3622152359826448f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-003r-9000000000-d5bb693fadd752735f312012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-014l-9000000000-8132ea67e057a3dd9c802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-014l-9100000000-a5bdece739d0cb5bf6292012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-015c-9200000000-eea073073c86ea4d9a382012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol EI-B (SHIMADZU QP-1000) , Positive-QTOFsplash10-0006-9000000000-0625da1bcd5a7d1938a62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-014l-9000000000-7b5a5cfbbe0b42fdd23e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Geraniol n/a 10V, negative-QTOFsplash10-0a4i-0900000000-73a127efb4137eb425802020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 10V, Positive-QTOFsplash10-0a4r-1900000000-3d437630e5bec67a7e072016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 20V, Positive-QTOFsplash10-052r-8900000000-0e505c85cec6344cab5c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 40V, Positive-QTOFsplash10-0gb9-9100000000-c7400df359a9559bd5942016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 10V, Negative-QTOFsplash10-0udi-0900000000-113756054eed13d33ee42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 20V, Negative-QTOFsplash10-0fk9-0900000000-dea43b41c5b791cef9d22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 40V, Negative-QTOFsplash10-0aou-9800000000-c028a2bd6550260942512016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 10V, Positive-QTOFsplash10-00lr-9100000000-6e205fbbb6213cf2eb8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 20V, Positive-QTOFsplash10-001i-9000000000-a55b9b951ba285782da92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 40V, Positive-QTOFsplash10-00kf-9000000000-29f4b3188008e31f7b9f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 10V, Negative-QTOFsplash10-0udi-0900000000-d3a143bdeacdf3ef0e942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 20V, Negative-QTOFsplash10-00di-0900000000-f29389e574ed8f84a6832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geraniol 40V, Negative-QTOFsplash10-014i-9100000000-1a426588f258e723527c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothautism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014945
KNApSAcK IDC00000855
Chemspider ID558917
KEGG Compound IDC09871
BioCyc IDCPD-7978
BiGG IDNot Available
Wikipedia LinkNerol
METLIN IDNot Available
PubChem Compound643820
PDB IDNot Available
ChEBI ID29452
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008952
References
Synthesis ReferenceVerley, A. Nerol. (1919), GB 127575 19190521 CAN 13:12091 AN 1919:12091
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. Muller GC, Junnila A, Butler J, Kravchenko VD, Revay EE, Weiss RW, Schlein Y: Efficacy of the botanical repellents geraniol, linalool, and citronella against mosquitoes. J Vector Ecol. 2009 Jun;34(1):2-8. doi: 10.1111/j.1948-7134.2009.00002.x. [PubMed:20836800 ]