Np mrd loader

Showing NP-Card for Geraniol (NP0000775)

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Record Information
Version2.0
Created at2007-01-22 23:21:34 UTC
Updated at2024-09-03 04:22:15 UTC
NP-MRD IDNP0000775
Natural Product DOIhttps://doi.org/10.57994/2790
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000775 (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 NP0000775 (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 NP0000775 (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>
NP0000775

> <DATABASE_NAME>
NP-MRD

> <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 NP0000775 (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

PDB for NP0000775 (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 NP0000775 (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 NP0000775 (Geraniol)

CC(C)=CCC\C(C)=C/CO
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INCHI for NP0000775 (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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View in JSmol
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
(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
Geraniol, 2-(14)C-labeled, (e)-isomerHMDB
Geraniol, titanium (4+) saltHMDB
Geraniol, (Z)-isomerHMDB
Geraniol, 1-(14)C-labeled, (e)-isomerHMDB
Geraniol, (e)-isomerHMDB
(Z)-3,7-Dimethyl-2,6-octadienolHMDB
(Z)-3,7-Dimethyloct-2,6-diene-1-olHMDB
(Z)-NerolHMDB
3,7-Dimethyl-cis-2,6-octadien-1-olHMDB
cis-1-Hydroxy-3,7-dimethyl-2,6-octadieneHMDB
beta-NerolHMDB
Β-nerolHMDB
GeraniolMeSH
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-09-06View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 200, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-16View Spectrum
Species
Species of Origin
Species NameSourceReference
Acca sellowianaKNApSAcK Database
Agathosma betulinaLOTUS Database
Aleuroglyphus ovatusLOTUS Database
Aloe arborescensLOTUS Database
Aloysia citrodoraLOTUS Database
Anthemis cotulaLOTUS Database
Artemisia absinthiumLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Aster scaberLOTUS Database
Atalantia buxifoliaLOTUS Database
Austromyrtus dulcisLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Bellis perennisLOTUS Database
Blepharocalyx salicifoliusLOTUS Database
Bupleurum fruticosumLOTUS Database
Calyptranthes spruceanaLOTUS Database
Cananga odorataKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Castanopsis cuspidataLOTUS Database
Catha edulisLOTUS Database
Centella asiaticaLOTUS Database
Cinnamomum burmanniLOTUS Database
Cinnamomum verumFooDB
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiifoliaFooDB
Citrus aurantiumLOTUS Database
Citrus aurantium var.amaraKNApSAcK Database
Citrus grandisKNApSAcK Database
Citrus iyoLOTUS Database
Citrus junosKNApSAcK Database
Citrus laurifoliusKNApSAcK Database
Citrus limettioidesKNApSAcK Database
Citrus limonFooDB
Citrus maximaFooDB
Citrus medicaLOTUS Database
Citrus paradisiKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Citrus trifoliataLOTUS Database
Citrus wilsoniiLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cleistopholis patensLOTUS Database
Coriandrum sativumLOTUS Database
Coriandrum sativum L.FooDB
Cryptomeria japonicaLOTUS Database
Curcuma longaLOTUS Database
Curcuma manggaKNApSAcK Database
Cymbopogon citratusKNApSAcK Database
Cymbopogon flexuosusLOTUS Database
Cymbopogon martiniiLOTUS Database
Dactylanthus tayloriiLOTUS Database
Daphne papyraceaLOTUS Database
Diplotaenia cachrydifoliaLOTUS Database
Dracocephalum moldavicumKNApSAcK Database
Dryopteris filix-masLOTUS Database
Elettaria cardamomumFooDB
Elsholtzia ciliataLOTUS Database
Elsholtzia pilosaLOTUS Database
Eremothecium ashbyiLOTUS Database
Eremothecium gossypiiLOTUS Database
Erigeron canadensisLOTUS Database
Eucalyptus citriodoraKNApSAcK Database
Eucalyptus populneaLOTUS Database
Eucalyptus pulverulentaLOTUS Database
Eupatorium cannabinumLOTUS Database
Gossypium hirsutumLOTUS Database
Hamamelis virginianaLOTUS Database
Helichrysum italicumLOTUS Database
Helichrysum odoratissimumLOTUS Database
Heracleum dissectumLOTUS Database
Hyssopus officinalis L.FooDB
Juniperus communisLOTUS Database
Lantana camaraLOTUS Database
Laurus nobilis L.FooDB
Lavandula angustifoliaLOTUS Database
Litchi chinensisLOTUS Database
Litsea cubebaKNApSAcK Database
Mangifera indicaFooDB
Matricaria chamomillaLOTUS Database
Melissa officinalisKNApSAcK Database
Melissa officinalis L.FooDB
Mentha piperitaLOTUS Database
Mentha spicataLOTUS Database
Mentha x piperitaFooDB
Monarda fistulosaLOTUS Database
Myristica fragransFooDB
Myrtus communisKNApSAcK Database
Narcissus tazettaLOTUS Database
Nicotiana benthamianaKNApSAcK Database
Nicotiana tobacumKNApSAcK Database
Ocimum basilicumFooDB
Oecophylla smaragdinaLOTUS Database
Origanum majoranaLOTUS Database
Origanum vulgareFooDB
Osmanthus fragransKNApSAcK Database
Paeonia lactifloraLOTUS Database
Pelargonium citronellumLOTUS Database
Pelargonium graveolensKNApSAcK Database
Pelargonium quercifoliumLOTUS Database
Phagnalon sordidumKNApSAcK Database
Piper arboreumKNApSAcK Database
Piper fimbriulatumKNApSAcK Database
Piper nigrumKNApSAcK Database
Pityophthorus pityographusLOTUS Database
Polygala senegaLOTUS Database
Prunus armeniacaLOTUS Database
Psiadia altissimaLOTUS Database
Rhanterium epapposumLOTUS Database
Rhodiola roseaLOTUS Database
Rhodiola rosea L.KNApSAcK Database
Rhododendron mucronulatumLOTUS Database
Robinia pseudoacaciaLOTUS Database
Rosa caninaLOTUS Database
Rosa centifoliaLOTUS Database
Rosa damascenaLOTUS Database
Rosa gallicaLOTUS Database
Rosa rugosaKNApSAcK Database
Salvia absconditifloraLOTUS Database
Salvia fruticosaLOTUS Database
Salvia rosmarinusFooDB
Salvia sclareaLOTUS Database
Sambucus nigraFooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Satureja thymbraLOTUS Database
Sideritis tragoriganumLOTUS Database
Solanum habrochaitesLOTUS Database
Solanum tuberosumLOTUS Database
Spondias mombinLOTUS Database
Syzygium jambosLOTUS Database
Tamarindus indicaFooDB
Tanacetum vulgareLOTUS Database
Teucrium cypriumLOTUS Database
Teucrium poliumLOTUS Database
Teucrium scorodoniaLOTUS Database
Thapsia villosaLOTUS Database
Thymbra capitataLOTUS Database
Thymus citriodorusLOTUS Database
Thymus longicaulisLOTUS Database
Thymus marschallianusLOTUS Database
Thymus sibthorpiiLOTUS Database
Thymus sipyleusLOTUS Database
Thymus vulgarisKNApSAcK Database
Tilia L.FooDB
Tordylium apulumLOTUS Database
Trifolium repensKNApSAcK Database
Vaccinium asheiLOTUS Database
Vaccinium corymbosumFooDB
Vaccinium macrocarponLOTUS Database
Vaccinium myrtillusFooDB
VitisFooDB
Vitis rotundifoliaLOTUS Database
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Zanthoxylum bungeanumLOTUS Database
Zingiber officinaleKNApSAcK Database
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
Physical Properties
StateLiquid
Experimental 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., Wyllie, S. G., & Markham, J. (1999). Determination of octanol-water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 864(2), 221-228.
Predicted 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
HMDB IDHMDB0005812
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1008952
References
General References
  1. 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 ]
  2. Miron D, Cornelio R, Troleis J, Mariath J, Zimmer AR, Mayorga P, Schapoval EE: Influence of penetration enhancers and molecular weight in antifungals permeation through bovine hoof membranes and prediction of efficacy in human nails. Eur J Pharm Sci. 2014 Jan 23;51:20-5. doi: 10.1016/j.ejps.2013.08.032. Epub 2013 Aug 30. [PubMed:23999034 ]
  3. Kpoviessi S, Bero J, Agbani P, Gbaguidi F, Kpadonou-Kpoviessi B, Sinsin B, Accrombessi G, Frederich M, Moudachirou M, Quetin-Leclercq J: Chemical composition, cytotoxicity and in vitro antitrypanosomal and antiplasmodial activity of the essential oils of four Cymbopogon species from Benin. J Ethnopharmacol. 2014;151(1):652-9. doi: 10.1016/j.jep.2013.11.027. Epub 2013 Nov 21. [PubMed:24269775 ]
  4. Kubo K, Tsuji K, Mori A, Ujiie S: Synthesis and properties of cholesteryl 4-(Alkanoylamino)benzoates: liquid crystals and organogelators. J Oleo Sci. 2014;63(4):401-6. doi: 10.5650/jos.ess13160. Epub 2014 Mar 5. [PubMed:24599108 ]