MiMeDB: Showing metabocard for Cycloartenol (MMDBc0052978)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:10:48 UTC

Update Date

2024-04-30 20:45:45 UTC

Metabolite ID

MMDBc0052978

Metabolite Identification

Common Name

Cycloartenol

Description

Cycloartenol is found in alcoholic beverages. Cycloartenol is a constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023582D          

 31 35  0  0  0  0            999 V2000
    7.8484    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5248    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9030    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  2  0  0  0  0
 21  3  1  0  0  0  0
 21 10  1  0  0  0  0
 22 13  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 14  1  0  0  0  0
 26  4  1  0  0  0  0
 26  5  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27  6  1  0  0  0  0
 27 17  1  0  0  0  0
 27 22  1  0  0  0  0
 28  7  1  0  0  0  0
 28 15  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 29 16  1  0  0  0  0
 29 19  1  0  0  0  0
 29 23  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 29  1  0  0  0  0
 31 25  1  0  0  0  0
M  END


  Mrv1652306222023582D          

 31 35  0  0  0  0            999 V2000
    7.8484    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5248    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9030    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 18 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  2  0  0  0  0
 21  3  1  0  0  0  0
 21 10  1  0  0  0  0
 22 13  1  0  0  0  0
 22 21  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 14  1  0  0  0  0
 26  4  1  0  0  0  0
 26  5  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27  6  1  0  0  0  0
 27 17  1  0  0  0  0
 27 22  1  0  0  0  0
 28  7  1  0  0  0  0
 28 15  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 29 16  1  0  0  0  0
 29 19  1  0  0  0  0
 29 23  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 29  1  0  0  0  0
 31 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052978

> <DATABASE_NAME>
MIME

> <SMILES>
CC(CCC=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3

> <INCHI_KEY>
ONQRKEUAIJMULO-UHFFFAOYSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.0693811373927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <ALOGPS_LOGP>
6.66

> <JCHEM_LOGP>
7.547662379333333

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489408976606935

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351325136321267

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
132.0332

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      14.650   4.487   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.180   3.482   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.968   6.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.007   0.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.855   0.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.735   5.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.172   1.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.019   6.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.544   6.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.074   5.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.985   0.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.501   0.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.031   2.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.993   4.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.756   1.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.523   4.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.071   5.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.555   5.071   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.039   4.799   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.125   4.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.548   5.330   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.603   4.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.993   1.903   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.025   2.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.516   2.809   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.523   1.632   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.064   4.164   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.541   2.716   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.516   3.351   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.032   3.622   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.032   2.538   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   26                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   28                                                            
CONECT    8    9   10                                                       
CONECT    9    8   20                                                       
CONECT   10    8   21                                                       
CONECT   11   12   23                                                       
CONECT   12   11   24                                                       
CONECT   13   15   22                                                       
CONECT   14   16   25                                                       
CONECT   15   13   28                                                       
CONECT   16   14   29                                                       
CONECT   17   18   27                                                       
CONECT   18   17   30                                                       
CONECT   19   29   30                                                       
CONECT   20    1    2    9                                                  
CONECT   21    3   10   22                                                  
CONECT   22   13   21   27                                                  
CONECT   23   11   26   29                                                  
CONECT   24   12   28   30                                                  
CONECT   25   14   26   31                                                  
CONECT   26    4    5   23   25                                             
CONECT   27    6   17   22   28                                             
CONECT   28    7   15   24   27                                             
CONECT   29   16   19   23   30                                             
CONECT   30   18   19   24   29                                             
CONECT   31   25                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

Synonyms

Value	Source
9,19-Cyclo-9beta-lanost-24-en-3beta-ol	HMDB
9,19-Cycloart-24-ene, 3beta-ol	HMDB
9beta,19-Cyclo-24-lanosten-3beta-ol	HMDB
9beta,19-Cyclolanost-24-en-3beta-ol	HMDB
Artosenol	HMDB
Handianol	HMDB
Cycloarterenol	MeSH
Cycloartenol	MeSH

Molecular Formula

C₃₀H₅₀O

Average Mass

426.7174

Monoisotopic Mass

426.386166222

IUPAC Name

7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

Traditional Name

7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C

InChI Identifier

InChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3

InChI Key

ONQRKEUAIJMULO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a steroid (CYCLOARTENOL )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.6e-05 g/L	ALOGPS
logP	6.66	ALOGPS
logP	7.55	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	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	4	ChemAxon
Refractivity	132.03 m³·mol⁻¹	ChemAxon
Polarizability	55.07 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3129500000-84dc7a934204a370748a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00lr-4011900000-88cf4a746167f7db19cb	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0003900000-ab3e1619815ddc34b3ae	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-1019400000-e52ce1479e1220bb23e3	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ug0-2039000000-28a8e4b53c1973a3ebd2	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-459890f27580d9795c97	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-280c456ab6df8a80788d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-1009400000-74ba59f4db9c4a4d312c	2016-08-03	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	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0036591

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

Cycloartenol

METLIN ID

Not Available

PubChem Compound

500213

PDB ID

Not Available

ChEBI ID

17030

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ahumada C, Saenz T, Garcia D, De La Puerta R, Fernandez A, Martinez E: The effects of a triterpene fraction isolated from Crataegus monogyna Jacq. on different acute inflammation models in rats and mice. Leucocyte migration and phospholipase A2 inhibition. J Pharm Pharmacol. 1997 Mar;49(3):329-31. doi: 10.1111/j.2042-7158.1997.tb06806.x. [PubMed:9231356 ]
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 Cycloartenol (MMDBc0052978)

MOL for #<Metabolite:0x00007fecda676c08>

3D MOL for #<Metabolite:0x00007fecda676c08>

3D SDF for #<Metabolite:0x00007fecda676c08>

3D-SDF for #<Metabolite:0x00007fecda676c08>

PDB for #<Metabolite:0x00007fecda676c08>

3D PDB for #<Metabolite:0x00007fecda676c08>

SMILES for #<Metabolite:0x00007fecda676c08>

INCHI for #<Metabolite:0x00007fecda676c08>

Structure for #<Metabolite:0x00007fecda676c08>

3D Structure for #<Metabolite:0x00007fecda676c08>