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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:40:17 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035662

Secondary Accession Numbers

HMDB35662

Metabolite Identification

Common Name

Nerolidol

Description

Nerolidol, also known as fema 2772 or stirrup, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Nerolidol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243611
     RDKit          3D
(S)-(+)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.6422    1.7764   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    0.7698   -0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4383    0.6888    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3242   -0.7476    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048    1.5297    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4076    0.9861   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    0.9948   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.2221   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -0.8955   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.3601   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -2.1259   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -2.0058    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -0.9637    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    0.0067    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0659    1.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    0.1363   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    2.5470    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6365    1.8576   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1121   -0.0235   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439   -0.8275    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3264   -1.2344    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -1.2868   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854    1.0376    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212    0.3028   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6433    2.0054   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    1.2320   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    1.8921    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -0.6058    0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.6359   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344   -1.0390   -2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -0.2831   -2.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.9103   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229   -2.5439    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -1.7998   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894   -2.9566    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -0.9908    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    2.0642    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    0.9507    2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2306    0.9245    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    1.1037   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -0.7193   -0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    0.0334   -1.4093 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
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

  Mrv0541 02241220202D          

 16 15  0  0  0  0            999 V2000
   -3.9318   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889    0.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  3  0  0  0
  6 14  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
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035662

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(C)=CCCC(C)(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3

> <INCHI_KEY>
FQTLCLSUCSAZDY-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.71035715485764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,11-trimethyldodeca-1,6,10-trien-3-ol

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
4.307206727666666

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.459388332120984

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2856635435302817

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
74.00919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nerolidol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243611
     RDKit          3D
(S)-(+)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.6422    1.7764   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    0.7698   -0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4383    0.6888    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3242   -0.7476    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048    1.5297    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4076    0.9861   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    0.9948   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.2221   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -0.8955   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.3601   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -2.1259   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -2.0058    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -0.9637    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    0.0067    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0659    1.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    0.1363   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    2.5470    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6365    1.8576   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1121   -0.0235   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439   -0.8275    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3264   -1.2344    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -1.2868   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854    1.0376    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212    0.3028   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6433    2.0054   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    1.2320   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    1.8921    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -0.6058    0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.6359   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344   -1.0390   -2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -0.2831   -2.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.9103   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229   -2.5439    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -1.7998   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894   -2.9566    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -0.9908    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    2.0642    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    0.9507    2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2306    0.9245    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    1.1037   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -0.7193   -0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    0.0334   -1.4093 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
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.339  -1.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.005  -0.387   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.671  -1.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.336  -0.387   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002  -1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -0.387   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -1.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -0.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.336  -1.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.671  -0.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.005  -1.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.339  -0.387   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.005   1.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667   1.156   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.899   0.950   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.442   0.950   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14    6                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0243606
HETATM    1  C1  UNL     1      -5.886   0.780  -1.774  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.796   0.976  -1.057  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.112  -0.142  -0.412  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.690  -0.346   0.969  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.125  -1.319  -1.115  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.615   0.222  -0.210  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.956  -0.933   0.446  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.535  -0.909   0.739  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.382  -0.050   0.413  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.188   1.168  -0.376  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.797  -0.368   0.916  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.721  -0.510  -0.269  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.073  -0.815   0.252  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.108  -0.004  -0.001  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.471  -0.315   0.526  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.881   1.207  -0.811  1.00  0.00           C  
HETATM   17  H1  UNL     1      -6.299  -0.214  -1.900  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.408   1.595  -2.260  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.415   1.977  -0.954  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.778  -0.114   0.992  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.558  -1.427   1.208  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.150   0.322   1.659  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.240  -2.124  -0.560  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.227   0.542  -1.173  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.632   1.056   0.561  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.472  -1.038   1.470  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.232  -1.902  -0.092  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.144  -1.782   1.358  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.018   0.872  -1.451  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.602   1.810   0.022  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.180   1.727  -0.370  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.142   0.491   1.510  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.770  -1.272   1.518  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.730   0.423  -0.856  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.397  -1.359  -0.910  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.244  -1.701   0.845  1.00  0.00           H  
HETATM   37  H21 UNL     1       6.462  -1.361   0.891  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.683   0.398   1.330  1.00  0.00           H  
HETATM   39  H23 UNL     1       7.174  -0.172  -0.321  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.094   1.844  -0.329  1.00  0.00           H  
HETATM   41  H25 UNL     1       5.799   1.807  -0.833  1.00  0.00           H  
HETATM   42  H26 UNL     1       4.554   0.959  -1.839  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    5    6
CONECT    4   20   21   22
CONECT    5   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9    9   28
CONECT    9   10   11
CONECT   10   29   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   14   36
CONECT   14   15   16
CONECT   15   37   38   39
CONECT   16   40   41   42
END

HMDB0243611
     RDKit          3D
(S)-(+)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.6422    1.7764   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    0.7698   -0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4383    0.6888    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3242   -0.7476    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048    1.5297    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4076    0.9861   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    0.9948   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972   -0.2221   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -0.8955   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.3601   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -2.1259   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -2.0058    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -0.9637    1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209    0.0067    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0659    1.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    0.1363   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    2.5470    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6365    1.8576   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1121   -0.0235   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439   -0.8275    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3264   -1.2344    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792   -1.2868   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854    1.0376    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212    0.3028   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6433    2.0054   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    1.2320   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    1.8921    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -0.6058    0.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401    0.6359   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344   -1.0390   -2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662   -0.2831   -2.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.9103   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6229   -2.5439    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -1.7998   -0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894   -2.9566    0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -0.9908    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    2.0642    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    0.9507    2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2306    0.9245    2.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    1.1037   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349   -0.7193   -0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    0.0334   -1.4093 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
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	ChEBI
3-Hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene	ChEBI
FEMA 2772	ChEBI
Stirrup	ChEBI
(+/-)-nerolidol	HMDB
Humbertiol?	HMDB
Melaleucol	HMDB
Peruviol	HMDB, MeSH
Nerolidol, (S-(Z))-isomer	MeSH
Nerolidol, (Z)-isomer	MeSH
Nerolidol	MeSH
Nerolidol, (e)-isomer	MeSH
Nerolidol, (S-(e))-isomer	MeSH

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

3,7,11-trimethyldodeca-1,6,10-trien-3-ol

Traditional Name

nerolidol

CAS Registry Number

7212-44-4

SMILES

CC(C)=CCCC(C)=CCCC(C)(O)C=C

InChI Identifier

InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3

InChI Key

FQTLCLSUCSAZDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

<i>E</i>-nerolidol (CPD-8843 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035662)

Source

Endogenous

Endogenous (HMDB: HMDB0035662)

Plant

Plant (HMDB: HMDB0035662)
Cucurbitaceae (HMDB: HMDB0035662)

Animal

Animal (HMDB: HMDB0035662)

Exogenous

Food

Food (HMDB: HMDB0035662)

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)

Tea

Gourd

Bitter gourd (FooDB: FOOD00115)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0035662)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035662)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035662)

Lipid metabolism pathway (HMDB: HMDB0035662)

Cellular process

Cell signaling (HMDB: HMDB0035662)

Biochemical process

Lipid transport (HMDB: HMDB0035662)

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0035662)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035662)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0035662)
Flavoring Agent (HMDB: HMDB0035662)

Agriculture

Pesticide

Nematicide (HMDB: HMDB0035662)

Pesticide (HMDB: HMDB0035662)

Fragrance (HMDB: HMDB0035662)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	114.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.53 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.682 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.55	ALOGPS
logP	4.31	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.46	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.01 m³·mol⁻¹	ChemAxon
Polarizability	28.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.989	31661259
DarkChem	[M-H]-	154.92	31661259
DeepCCS	[M+H]+	153.159	30932474
DeepCCS	[M-H]-	150.801	30932474
DeepCCS	[M-2H]-	185.791	30932474
DeepCCS	[M+Na]+	160.957	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	162.7	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nerolidol	CC(C)=CCCC(C)=CCCC(C)(O)C=C	2043.1	Standard polar	33892256
Nerolidol	CC(C)=CCCC(C)=CCCC(C)(O)C=C	1547.7	Standard non polar	33892256
Nerolidol	CC(C)=CCCC(C)=CCCC(C)(O)C=C	1583.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nerolidol,1TMS,isomer #1	C=CC(C)(CCC=C(C)CCC=C(C)C)O[Si](C)(C)C	1670.2	Semi standard non polar	33892256
Nerolidol,1TBDMS,isomer #1	C=CC(C)(CCC=C(C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1910.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9510000000-a3e895d52dc707efac8d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (1 TMS) - 70eV, Positive	splash10-009f-9450000000-0e9301ccd24a06b7cb6b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nerolidol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 10V, Positive-QTOF	splash10-0ab9-0490000000-161e693347ad291e0fbd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 20V, Positive-QTOF	splash10-0avr-8930000000-9d44e8ed0962b3b4a6e5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 40V, Positive-QTOF	splash10-0gc0-9200000000-e440a4caa7377830e550	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 10V, Negative-QTOF	splash10-00di-0090000000-ccfe5910ac69a0881b78	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 20V, Negative-QTOF	splash10-0fk9-0290000000-472fb15ead3e188bca2a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 40V, Negative-QTOF	splash10-0avi-8920000000-8d83134760e8882365f8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 10V, Positive-QTOF	splash10-00e9-6920000000-ad48f7ac5c3e7a13b831	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 20V, Positive-QTOF	splash10-008a-9500000000-2a007f295fe4ebe9dfb6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 40V, Positive-QTOF	splash10-00o3-9100000000-9e89155500d705ca9581	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 20V, Negative-QTOF	splash10-00di-4390000000-1e6703c26890b0ed7c60	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nerolidol 40V, Negative-QTOF	splash10-006t-8910000000-f204944da3e1544896d6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014378

KNApSAcK ID

C00003166

Chemspider ID

8549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nerolidol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

7524

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1009032

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lee SJ, Han JI, Lee GS, Park MJ, Choi IG, Na KJ, Jeung EB: Antifungal effect of eugenol and nerolidol against Microsporum gypseum in a guinea pig model. Biol Pharm Bull. 2007 Jan;30(1):184-8. [PubMed:17202684 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Nerolidol (HMDB0035662)

MOL for HMDB0035662 (Nerolidol)

3D MOL for HMDB0035662 (Nerolidol)

3D SDF for HMDB0035662 (Nerolidol)

3D-SDF for HMDB0035662 (Nerolidol)

PDB for HMDB0035662 (Nerolidol)

3D PDB for HMDB0035662 (Nerolidol)

SMILES for HMDB0035662 (Nerolidol)

INCHI for HMDB0035662 (Nerolidol)

Structure for HMDB0035662 (Nerolidol)

3D Structure for HMDB0035662 (Nerolidol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra