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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:19:22 UTC

Update Date

2023-02-21 17:28:54 UTC

HMDB ID

HMDB0041629

Secondary Accession Numbers

HMDB41629

Metabolite Identification

Common Name

(3S,6E)-Nerolidol

Description

(3S,6E)-Nerolidol, also known as nerolidol or peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (3S,6E)-nerolidol is considered to be an isoprenoid lipid molecule. (3S,6E)-Nerolidol is an isomer of nerolidol, a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers.

Structure

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

HMDB0041629
     RDKit          3D
(3S,6E)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.5527    1.8049   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.8550    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3736   -0.2956   -0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2469   -1.4827    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.6585   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223   -0.0028   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082    0.3206    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.6136   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -0.1075   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -1.2233    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.2516   -0.6635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7294    0.6013    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.9623   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2580    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    0.6561   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391   -0.9069    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205    2.6592    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7509    1.7437   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    0.9154    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1856   -2.0912    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -2.1161    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090   -1.1766    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -1.1065   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.9100   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796    0.8203   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    1.2304    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026   -0.5093    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446    1.4380   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7922    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.9103    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -1.8474    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028   -0.6502   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    1.0432   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129   -0.2994    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    1.4924    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    1.7898   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1852    0.9988   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.5065    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -0.1985   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -1.6647    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -0.5948    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0286   -1.4163    1.0814 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  6
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  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


  Mrv1652309102019502D          

 16 15  0  0  0  0            999 V2000
 9983.4462 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1596 9982.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7313 9982.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8751 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0166 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7313 9983.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.5906 9982.8807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9981.2997 9982.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3040 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.0009 9983.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1762 9983.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.5850 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0195 9982.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8704 9982.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.1557 9982.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8704 9983.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  1  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041629

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\CC[C@](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/b14-11+/t15-/m1/s1

> <INCHI_KEY>
FQTLCLSUCSAZDY-ATGUSINASA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.708505135468293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6E)-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>
74.0092

> <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

$$$$

HMDB0041629
     RDKit          3D
(3S,6E)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.5527    1.8049   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.8550    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3736   -0.2956   -0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2469   -1.4827    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.6585   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223   -0.0028   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082    0.3206    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.6136   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -0.1075   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -1.2233    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.2516   -0.6635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7294    0.6013    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.9623   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2580    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    0.6561   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391   -0.9069    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205    2.6592    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7509    1.7437   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    0.9154    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1856   -2.0912    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -2.1161    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090   -1.1766    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -1.1065   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.9100   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796    0.8203   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    1.2304    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026   -0.5093    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446    1.4380   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7922    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.9103    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -1.8474    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028   -0.6502   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    1.0432   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129   -0.2994    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    1.4924    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    1.7898   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1852    0.9988   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.5065    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -0.1985   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -1.6647    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -0.5948    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0286   -1.4163    1.0814 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  6
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  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                                 10-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-20         0                                  
HETATM    1  C   UNK     0    8635.7668633.942   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8637.0988634.711   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8634.4328634.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8638.4348633.942   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8633.0988633.942   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8634.4328636.251   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8639.7698634.711   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8631.7598634.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8641.1018633.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8640.5358636.043   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8638.9968636.043   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8630.4258633.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8642.4368634.711   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8629.0918634.711   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8627.7578633.942   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8629.0918636.251   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    3                                                            
CONECT    7    4    9   10   11                                             
CONECT    8    5   12                                                       
CONECT    9    7   13                                                       
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8   14                                                       
CONECT   13    9                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0041629
HETATM    1  C1  UNL     1      -5.553   1.805  -0.097  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.869   0.855   0.510  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.374  -0.296  -0.252  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.247  -1.483   0.678  1.00  0.00           C  
HETATM    5  O1  UNL     1      -5.222  -0.659  -1.299  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.022  -0.003  -0.871  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.008   0.321   0.206  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.670   0.614  -0.361  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.414  -0.107  -0.051  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.233  -1.223   0.889  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.722   0.252  -0.663  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.729   0.601   0.408  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.039   0.962  -0.172  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.100   0.258   0.145  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.416   0.656  -0.466  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.039  -0.907   1.079  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.921   2.659   0.469  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.751   1.744  -1.148  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.668   0.915   1.572  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.186  -2.091   0.653  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.375  -2.116   0.350  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.009  -1.177   1.711  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.724  -1.107  -2.036  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.740  -0.910  -1.444  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.080   0.820  -1.603  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.342   1.230   0.745  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.003  -0.509   0.920  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.545   1.438  -1.053  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.163  -0.792   1.841  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.567  -1.910   0.488  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.118  -1.847   1.033  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.103  -0.650  -1.185  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.610   1.043  -1.431  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.813  -0.299   1.062  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.398   1.492   1.004  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.111   1.790  -0.842  1.00  0.00           H  
HETATM   37  H21 UNL     1       6.185   0.999  -1.505  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.811   1.507   0.102  1.00  0.00           H  
HETATM   39  H23 UNL     1       7.122  -0.199  -0.480  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.303  -1.665   0.762  1.00  0.00           H  
HETATM   41  H25 UNL     1       4.745  -0.595   2.110  1.00  0.00           H  
HETATM   42  H26 UNL     1       6.029  -1.416   1.081  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

HMDB0041629
     RDKit          3D
(3S,6E)-Nerolidol
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.5527    1.8049   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    0.8550    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3736   -0.2956   -0.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2469   -1.4827    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222   -0.6585   -1.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223   -0.0028   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082    0.3206    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.6136   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -0.1075   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -1.2233    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.2516   -0.6635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7294    0.6013    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.9623   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2580    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159    0.6561   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391   -0.9069    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205    2.6592    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7509    1.7437   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    0.9154    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1856   -2.0912    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -2.1161    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090   -1.1766    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -1.1065   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.9100   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796    0.8203   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    1.2304    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026   -0.5093    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446    1.4380   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7922    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.9103    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175   -1.8474    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028   -0.6502   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    1.0432   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129   -0.2994    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    1.4924    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    1.7898   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1852    0.9988   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.5065    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1215   -0.1985   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -1.6647    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -0.5948    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0286   -1.4163    1.0814 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  6
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  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
(S-(e))-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol	ChEBI
Nerolidol	HMDB
Nerolidol, (e)-isomer	HMDB
Nerolidol, (S-(e))-isomer	HMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
Nerolidol, (S-(Z))-isomer	HMDB
Peruviol	HMDB
Nerolidol, (Z)-isomer	HMDB
(+)-trans-Nerolidol	HMDB
(3S)-(e)-Nerolidol	HMDB
(3S)-trans-Nerolidol	HMDB
(3S,6E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
(3S,e)-Nerolidol	HMDB
(S)-(+)-trans-Nerolidol	HMDB
(S)-trans-Nerolidol	HMDB
(S,e)-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol	HMDB
(S,e)-Nerolidol	HMDB
trans-(+)-Nerolidol	HMDB
(3S,6E)-Nerolidol	HMDB

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.372

Monoisotopic Molecular Weight

222.198365457

IUPAC Name

(3S,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

Traditional Name

nerolidol

CAS Registry Number

1119-38-6

SMILES

CC(C)=CCC\C(C)=C\CC[C@](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/b14-11+/t15-/m1/s1

InChI Key

FQTLCLSUCSAZDY-ATGUSINASA-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

nerolidol (CHEBI:59958 )
Acyclic farnesane sesquiterpenoids (C09704 )
Farnesenes (C09704 )
Acyclic farnesane sesquiterpenoids (LMPR0103010005 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041629)

Source

Endogenous

Endogenous (HMDB: HMDB0041629)

Animal

Animal (HMDB: HMDB0041629)

Exogenous

Food

Food (HMDB: HMDB0041629)

Exogenous (HMDB: HMDB0041629)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0041629)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0041629)

Lipid metabolism pathway (HMDB: HMDB0041629)

Cellular process

Cell signaling (HMDB: HMDB0041629)

Biochemical process

Lipid transport (HMDB: HMDB0041629)

Role

Biological role

Energy source (HMDB: HMDB0041629)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041629)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 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
DeepCCS	[M+H]+	158.472	30932474
DeepCCS	[M-H]-	156.114	30932474
DeepCCS	[M-2H]-	189.147	30932474
DeepCCS	[M+Na]+	164.565	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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	8.12 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0532 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2549.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	516.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	526.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1207.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	420.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	759.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	428.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3S,6E)-Nerolidol	CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C	2043.1	Standard polar	33892256
(3S,6E)-Nerolidol	CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C	1547.7	Standard non polar	33892256
(3S,6E)-Nerolidol	CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C	1583.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3S,6E)-Nerolidol,1TMS,isomer #1	C=C[C@](C)(CC/C=C(\C)CCC=C(C)C)O[Si](C)(C)C	1670.2	Semi standard non polar	33892256
(3S,6E)-Nerolidol,1TBDMS,isomer #1	C=C[C@](C)(CC/C=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 - (3S,6E)-Nerolidol GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3S,6E)-Nerolidol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - (3S,6E)-Nerolidol 10V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 20V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 40V, Positive-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 10V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 20V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 40V, Negative-QTOF	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 20V, Negative-QTOF	splash10-00di-4390000000-1e6703c26890b0ed7c60	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 40V, Negative-QTOF	splash10-006t-8910000000-f204944da3e1544896d6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 10V, Positive-QTOF	splash10-00e9-6920000000-ad48f7ac5c3e7a13b831	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 20V, Positive-QTOF	splash10-008a-9500000000-2a007f295fe4ebe9dfb6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,6E)-Nerolidol 40V, Positive-QTOF	splash10-00o3-9100000000-9e89155500d705ca9581	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281525

PDB ID

Not Available

ChEBI ID

59958

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1556301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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Showing metabocard for (3S,6E)-Nerolidol (HMDB0041629)

MOL for HMDB0041629 ((3S,6E)-Nerolidol)

3D MOL for HMDB0041629 ((3S,6E)-Nerolidol)

3D SDF for HMDB0041629 ((3S,6E)-Nerolidol)

3D-SDF for HMDB0041629 ((3S,6E)-Nerolidol)

PDB for HMDB0041629 ((3S,6E)-Nerolidol)

3D PDB for HMDB0041629 ((3S,6E)-Nerolidol)

SMILES for HMDB0041629 ((3S,6E)-Nerolidol)

INCHI for HMDB0041629 ((3S,6E)-Nerolidol)

Structure for HMDB0041629 ((3S,6E)-Nerolidol)

3D Structure for HMDB0041629 ((3S,6E)-Nerolidol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra