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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:06 UTC

Update Date

2023-02-21 17:19:23 UTC

HMDB ID

HMDB0030002

Secondary Accession Numbers

HMDB30002

Metabolite Identification

Common Name

(-)-Nopol

Description

(-)-Nopol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a significant number of articles have been published on (-)-Nopol.

Structure

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

HMDB0030002
     RDKit          3D
(-)-Nopol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.7106   -1.2388    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670   -0.2933    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    0.7940    1.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.1863   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    1.3771   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    1.0259   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.0909    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -0.4601    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564    0.5301    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817    0.7614   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.0275   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -1.1054   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.9418   -0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -1.2389    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -2.2774    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    0.3704    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299    1.5382    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    1.2840    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2585   -1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    1.7055   -2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562    2.2256   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870    1.7129   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -0.6338    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649   -1.4423    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    1.4595    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    0.1164    1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169    0.2784   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -1.9889    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -1.9679   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403   -0.9176   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11  2  1  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
M  END

HMDB0030002
     RDKit          3D
(-)-Nopol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.7106   -1.2388    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670   -0.2933    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    0.7940    1.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.1863   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    1.3771   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    1.0259   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.0909    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -0.4601    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564    0.5301    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817    0.7614   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.0275   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -1.1054   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.9418   -0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -1.2389    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -2.2774    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    0.3704    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299    1.5382    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    1.2840    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2585   -1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    1.7055   -2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562    2.2256   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870    1.7129   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -0.6338    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649   -1.4423    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    1.4595    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    0.1164    1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169    0.2784   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -1.9889    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -1.9679   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403   -0.9176   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11  2  1  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  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      -1.334  -0.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.524   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.293   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.213   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.021  -1.762   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.946  -2.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.215   1.891   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.215   3.293   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    1    3    9   10                                             
CONECT    8    6   11                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0030002
HETATM    1  C1  UNL     1      -2.711  -1.239   0.389  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.567  -0.293   0.232  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.534   0.794   1.249  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.461   0.186  -1.220  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.551   1.377  -1.267  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.768   1.026  -0.672  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.884  -0.091   0.040  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.043  -0.460   0.854  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.156   0.530   0.850  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.682   0.761  -0.417  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.271  -1.028  -0.009  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.677  -1.105  -1.488  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.508  -0.942  -0.318  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.061  -1.239   1.447  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.413  -2.277   0.131  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.865   0.370   2.217  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.330   1.538   0.969  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.571   1.284   1.383  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.402   0.258  -1.756  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.455   1.706  -2.318  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.956   2.226  -0.680  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.587   1.713  -0.852  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.735  -0.634   1.897  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.465  -1.442   0.495  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.831   1.460   1.355  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.984   0.116   1.464  1.00  0.00           H  
HETATM   27  H15 UNL     1       4.517   0.278  -0.596  1.00  0.00           H  
HETATM   28  H16 UNL     1      -0.144  -1.989   0.475  1.00  0.00           H  
HETATM   29  H17 UNL     1      -1.317  -1.968  -1.671  1.00  0.00           H  
HETATM   30  H18 UNL     1       0.140  -0.918  -2.183  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   11
CONECT    3   16   17   18
CONECT    4    5   12   19
CONECT    5    6   20   21
CONECT    6    7    7   22
CONECT    7    8   11
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   27
CONECT   11   12   28
CONECT   12   29   30
END

HMDB0030002
     RDKit          3D
(-)-Nopol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.7106   -1.2388    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670   -0.2933    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336    0.7940    1.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.1863   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    1.3771   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    1.0259   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840   -0.0909    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -0.4601    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564    0.5301    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6817    0.7614   -0.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -1.0275   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -1.1054   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077   -0.9418   -0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0613   -1.2389    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -2.2774    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8645    0.3704    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299    1.5382    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    1.2840    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2585   -1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    1.7055   -2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562    2.2256   -0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870    1.7129   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -0.6338    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649   -1.4423    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    1.4595    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    0.1164    1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169    0.2784   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -1.9889    0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -1.9679   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403   -0.9176   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11  2  1  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nopol	MeSH

Chemical Formula

C₁₁H₁₈O

Average Molecular Weight

166.26

Monoisotopic Molecular Weight

166.135765198

IUPAC Name

2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethan-1-ol

Traditional Name

2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethanol

CAS Registry Number

35836-73-8

SMILES

CC1(C)C2CC1C(CCO)=CC2

InChI Identifier

InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3

InChI Key

ROKSAUSPJGWCSM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030002)

Source

Endogenous

Endogenous (HMDB: HMDB0030002)

Plant

Plant (HMDB: HMDB0030002)

Animal

Animal (HMDB: HMDB0030002)

Exogenous

Food

Food (HMDB: HMDB0030002)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030002)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030002)

Lipid metabolism pathway (HMDB: HMDB0030002)

Cellular process

Cell signaling (HMDB: HMDB0030002)

Biochemical process

Lipid transport (HMDB: HMDB0030002)

Role

Biological role

Energy source (HMDB: HMDB0030002)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030002)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0030002)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	230.00 to 240.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	318.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.152 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	3.22	ALOGPS
logP	1.81	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.99	ChemAxon
pKa (Strongest Basic)	-1.9	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	2	ChemAxon
Refractivity	51.25 m³·mol⁻¹	ChemAxon
Polarizability	20.17 Å³	ChemAxon
Number of Rings	2	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]+	137.435	31661259
DarkChem	[M-H]-	133.875	31661259
DeepCCS	[M+H]+	140.772	30932474
DeepCCS	[M-H]-	137.48	30932474
DeepCCS	[M-2H]-	174.479	30932474
DeepCCS	[M+Na]+	149.805	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	132.8	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.1	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	144.5	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. Predicted by Afia on May 17, 2022.	4.19 minutes	32390414
Predicted by Siyang on May 30, 2022	12.016 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1808.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	358.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	147.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	428.6 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	538.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	953.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	339.2 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	1133.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	368.4 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	39.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Nopol	CC1(C)C2CC1C(CCO)=CC2	1883.7	Standard polar	33892256
(-)-Nopol	CC1(C)C2CC1C(CCO)=CC2	1284.7	Standard non polar	33892256
(-)-Nopol	CC1(C)C2CC1C(CCO)=CC2	1316.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Nopol,1TMS,isomer #1	CC1(C)C2CC=C(CCO[Si](C)(C)C)C1C2	1404.4	Semi standard non polar	33892256
(-)-Nopol,1TBDMS,isomer #1	CC1(C)C2CC=C(CCO[Si](C)(C)C(C)(C)C)C1C2	1665.4	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 - (-)-Nopol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00s6-5900000000-d23e455893d418d01858	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Nopol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9620000000-565e4a58ee8c637a6e52	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Nopol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-054o-9600000000-36499504cc88c9623c93	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 10V, Positive-QTOF	splash10-00kb-0900000000-b52f1a4c416c90f7666e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 20V, Positive-QTOF	splash10-0002-0900000000-20ad2500efd50a13fe6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 40V, Positive-QTOF	splash10-007k-0900000000-8cedaa08b51367c120fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 10V, Negative-QTOF	splash10-014i-0900000000-669afeea70039d5626c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 20V, Negative-QTOF	splash10-00kr-0900000000-7411e6ee830774016459	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 40V, Negative-QTOF	splash10-00re-2900000000-9a3b8943337fd74831d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 10V, Positive-QTOF	splash10-014i-0900000000-31eb65f0b47955870b8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 20V, Positive-QTOF	splash10-0002-0900000000-b5bef5289d2fee1873b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 40V, Positive-QTOF	splash10-0a4i-0900000000-dbcc9ddd2c6244883321	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 10V, Negative-QTOF	splash10-014i-0900000000-05af9fd30de6fd63473b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 20V, Negative-QTOF	splash10-014i-0900000000-a2f17ad3d8e232de73ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Nopol 40V, Negative-QTOF	splash10-014i-1900000000-8497c6b5069c96120315	2021-09-24	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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

FDB001291

KNApSAcK ID

Not Available

Chemspider ID

29138

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31408

PDB ID

Not Available

ChEBI ID

525644

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1108531

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 ]
(). 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 (-)-Nopol (HMDB0030002)

MOL for HMDB0030002 ((-)-Nopol)

3D MOL for HMDB0030002 ((-)-Nopol)

3D SDF for HMDB0030002 ((-)-Nopol)

3D-SDF for HMDB0030002 ((-)-Nopol)

PDB for HMDB0030002 ((-)-Nopol)

3D PDB for HMDB0030002 ((-)-Nopol)

SMILES for HMDB0030002 ((-)-Nopol)

INCHI for HMDB0030002 ((-)-Nopol)

Structure for HMDB0030002 ((-)-Nopol)

3D Structure for HMDB0030002 ((-)-Nopol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra