MiMeDB: Showing metabocard for Isocineole (MMDBc0047716)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:39:23 UTC

Update Date

2024-04-30 20:29:00 UTC

Metabolite ID

MMDBc0047716

Metabolite Identification

Common Name

Isocineole

Description

1,4-Cineole 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 1,4-Cineole.

Structure

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

HMDB0036096
     RDKit          3D
1,4-Cineole
 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.7253    0.6685    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.2770   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -0.9584   -1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    0.2084   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650   -0.7586    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587   -1.2131    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -0.1668   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -0.5194   -1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398    1.2163    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    1.5563    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436   -0.1455   -1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    1.7773    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600    0.4454    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366    0.1147    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834    1.1066   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350   -0.6522   -1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100   -1.6752   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -1.4158   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -0.2005    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541   -1.5974    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -2.1780    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -1.2336    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    0.3518   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -1.0575   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.2627   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    1.1732    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    1.9406   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139    2.3195   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    1.8792    1.3275 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 10  4  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
M  END

HMDB0036096
     RDKit          3D
1,4-Cineole
 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.7253    0.6685    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.2770   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -0.9584   -1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    0.2084   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650   -0.7586    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587   -1.2131    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -0.1668   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -0.5194   -1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398    1.2163    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    1.5563    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436   -0.1455   -1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    1.7773    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600    0.4454    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366    0.1147    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834    1.1066   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350   -0.6522   -1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100   -1.6752   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -1.4158   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -0.2005    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541   -1.5974    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -2.1780    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -1.2336    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    0.3518   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -1.0575   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.2627   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    1.1732    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    1.9406   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139    2.3195   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    1.8792    1.3275 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 10  4  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
M  END

COMPND    HMDB0036096
HETATM    1  C1  UNL     1      -2.725   0.668   0.563  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.755   0.277  -0.505  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.212  -0.958  -1.223  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.343   0.208  -0.034  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.065  -0.759   1.064  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.359  -1.213   0.705  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.730  -0.167  -0.304  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.927  -0.519  -1.096  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.740   1.216   0.288  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.240   1.556   0.329  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.544  -0.146  -1.081  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.736   1.777   0.758  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.760   0.445   0.188  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.537   0.115   1.487  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.783   1.107  -1.273  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.035  -0.652  -1.926  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.610  -1.675  -0.467  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.434  -1.416  -1.846  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.012  -0.201   2.042  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.754  -1.597   1.134  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.267  -2.178   0.179  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.010  -1.234   1.585  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.352   0.352  -1.609  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.643  -1.058  -0.452  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.605  -1.263  -1.877  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.068   1.173   1.360  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.314   1.941  -0.283  1.00  0.00           H  
HETATM   28  H17 UNL     1       0.014   2.320  -0.465  1.00  0.00           H  
HETATM   29  H18 UNL     1      -0.074   1.879   1.328  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   11
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9   11
CONECT    8   23   24   25
CONECT    9   10   26   27
CONECT   10   28   29
END

HMDB0036096
     RDKit          3D
1,4-Cineole
 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.7253    0.6685    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.2770   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -0.9584   -1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    0.2084   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650   -0.7586    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587   -1.2131    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -0.1668   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -0.5194   -1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398    1.2163    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    1.5563    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436   -0.1455   -1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    1.7773    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600    0.4454    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5366    0.1147    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834    1.1066   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350   -0.6522   -1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100   -1.6752   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -1.4158   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -0.2005    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541   -1.5974    1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -2.1780    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -1.2336    1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    0.3518   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -1.0575   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.2627   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    1.1732    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    1.9406   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139    2.3195   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    1.8792    1.3275 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 10  4  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 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
  9 27  1  0
 10 28  1  0
 10 29  1  0
M  END

Synonyms

Value	Source
1,4-Epoxy-p-menthane	Kegg
1,4-Cineol	HMDB
1-Isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptane	HMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane	HMDB
1-Isopropyl-4-methylbicyclo[2.2.1]heptane	HMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptane	HMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane	HMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane, 9ci	HMDB
7-oxabicyclo(2.2.1)Heptane, 1-isopropyl-4-methyl- (6ci)	HMDB
Isocineole	HMDB
Isocineple	HMDB
P-Cineole	HMDB
P-Menthane, 1,4-epoxy	HMDB

Molecular Formula

C₁₀H₁₈O

Average Mass

154.2493

Monoisotopic Mass

154.135765198

IUPAC Name

1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane

Traditional Name

1,4-cineol

CAS Registry Number

Not Available

SMILES

CC(C)C12CCC(C)(CC1)O2

InChI Identifier

InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3

InChI Key

RFFOTVCVTJUTAD-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

P-menthane monoterpenoid
Bicyclic monoterpenoid
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

monoterpenoid (CHEBI:80788 )
Cyclic monoterpenes (C16909 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.31	ALOGPS
logP	2.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.71 m³·mol⁻¹	ChemAxon
Polarizability	18.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ox-9300000000-b9a5b5d2f98cced31647	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01xx-9500000000-a318fb72cb983bf328bd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ox-9300000000-b9a5b5d2f98cced31647	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01xx-9500000000-a318fb72cb983bf328bd	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-4900000000-bdc12e60fcbd39f1835c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-dddd2f9cdd5cb5b07319	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-dceb1fb237319528cf1c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-2900000000-571ee3b396093a239686	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-f31d792cd2a066e8f6d8	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-3d49e541e98afbae6fdc	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zmr-2900000000-d8a5501eed1b480a13e2	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-dea631cb559c531e8d8b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1900000000-61a5843d11f2b1969caf	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08g0-2900000000-1ce225c60ad3a899db29	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054x-9700000000-0a3a8813a78b2bd04a55	2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit	Illicium verum	FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant	Calyx	Hibiscus sabdariffa	FooDB	31437929
Plant	Fruit	Citrus aurantiifolia	FooDB	31437929
Plant	Fruit	Elettaria cardamomum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0036096

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10106

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. 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 Isocineole (MMDBc0047716)

MOL for #<Metabolite:0x00007fecaf9d47b8>

3D MOL for #<Metabolite:0x00007fecaf9d47b8>

3D SDF for #<Metabolite:0x00007fecaf9d47b8>

3D-SDF for #<Metabolite:0x00007fecaf9d47b8>

PDB for #<Metabolite:0x00007fecaf9d47b8>

3D PDB for #<Metabolite:0x00007fecaf9d47b8>

SMILES for #<Metabolite:0x00007fecaf9d47b8>

INCHI for #<Metabolite:0x00007fecaf9d47b8>

Structure for #<Metabolite:0x00007fecaf9d47b8>

3D Structure for #<Metabolite:0x00007fecaf9d47b8>