MiMeDB: Showing metabocard for 3-Hydroxymyristate (MMDBc0000709)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:14 UTC

Update Date

2024-04-30 19:33:34 UTC

Metabolite ID

MMDBc0000709

Metabolite Identification

Common Name

3-Hydroxymyristate

Description

3-hydroxymyristate, also known as 3-Hydroxytetradecanoate(1-) or β-hydroxymyristic acid, is classified as a member of the long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 3-hydroxymyristate is considered to be a practically insoluble (in water) and a weak acidic compound. 3-hydroxymyristate can be found in feces.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305171802452D          

 17 16  0  0  0  0            999 V2000
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000709

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCC(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

> <INCHI_KEY>
ATRNZOYKSNPPBF-UHFFFAOYSA-N

> <FORMULA>
C14H28O3

> <MOLECULAR_WEIGHT>
244.3703

> <EXACT_MASS>
244.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.558238870709154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxytetradecanoic acid

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.136634380666667

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.3971

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-myristic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.197   6.462   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      29.864   6.462   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
3-Hydroxy-tetradecanoic acid	ChEBI
3-Hydroxymyristic acid	ChEBI
beta-Hydroxymyristic acid	ChEBI
beta-Hydroxytetradecanoic acid	ChEBI
3-Hydroxy-tetradecanoate	Generator
3-Hydroxymyristate	Generator
b-Hydroxymyristate	Generator
b-Hydroxymyristic acid	Generator
beta-Hydroxymyristate	Generator
Β-hydroxymyristate	Generator
Β-hydroxymyristic acid	Generator
b-Hydroxytetradecanoate	Generator
b-Hydroxytetradecanoic acid	Generator
beta-Hydroxytetradecanoate	Generator
Β-hydroxytetradecanoate	Generator
Β-hydroxytetradecanoic acid	Generator
3-Hydroxytetradecanoate	Generator
14:0(3-OH)	HMDB
beta-Hydroxymyristic acid, (R)-isomer	HMDB
3-Hydroxytetradecanoic acid	MeSH

Molecular Formula

C₁₄H₂₈O₃

Average Mass

244.3703

Monoisotopic Mass

244.203844762

IUPAC Name

3-hydroxytetradecanoic acid

Traditional Name

3-hydroxy-myristic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(O)CC(O)=O

InChI Identifier

InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

InChI Key

ATRNZOYKSNPPBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:85148 )
3-hydroxy monocarboxylic acid (CHEBI:85148 )
3-hydroxy fatty acid (CHEBI:85148 )
Hydroxy fatty acids (LMFA01050175 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	4.69	ALOGPS
logP	4.14	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	69.4 m³·mol⁻¹	ChemAxon
Polarizability	30.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-4961000000-5528c5db71884cb54509	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1920000000-4232a13b15fd6bcda6d4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9500000000-8a1445b437ad3096eea6	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-9142000000-2b802003b701914b13b7	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-3d8230895dab3bd2803c	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-4970000000-c730628afc4d9570bdf9	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9400000000-51c4168a9e617d26ff4a	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1390000000-5803d60e0c240534ca14	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a7m-4960000000-a807bdab3c0cb68c61f1	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5c-9600000000-58f9900cb39aba9c7f4f	2015-04-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025185	Adenosine triphosphate	diphosphate	Medium/long-chain-fatty-acid--CoA ligase FadD6	Ligation	RHEA	34755880
MMDBr0025186	Adenosine triphosphate	diphosphate	Medium/long-chain-fatty-acid--CoA ligase FadD6	Ligation	RHEA	34755880
MMDBr0028335	CL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/14:0(3-OH))	2-MLCL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/0:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028561	CL(12:0/14:0(3-OH)/12:0/14:0(3-OH))	2-MLCL(12:0/14:0(3-OH)/12:0/0:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0030039	CL(14:0(3-OH)/14:0(3-OH)/14:0/14:0)	2-MLCL(14:0(3-OH)/0:0/14:0/14:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0035750	CL(14:0/14:0(3-OH)/14:0/14:0)	3-Hydroxymyristate	Not Available	Deacylation	RHEA	34755880
MMDBr0034389	CL(16:0/14:0(3-OH)/16:0/14:0(3-OH))	2-MLCL(16:0/14:0(3-OH)/16:0/0:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0034919	CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(3-OH))	2-MLCL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/0:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0035751	CL(19:iso/14:0(3-OH)/14:0/14:0)	3-Hydroxymyristate	Not Available	Deacylation	RHEA	34755880
MMDBr0035522	CL(19:iso/14:0(3-OH)/19:iso/14:0(3-OH))	2-MLCL(19:iso/0:0/19:iso/14:0(3-OH))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0036134	tetradecanoate (n-C14:0)	3-Hydroxymyristate	Fatty-acid peroxygenase	Hydroxylation	RHEA	34755880
MMDBr0037478	PG(14:0(3-OH)/10:0(3-OH))	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037492	PG(14:0(3-OH)/10:0)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037524	PG(14:0(3-OH)/12:0(3-OH))	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037538	PG(14:0(3-OH)/12:0)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037567	PG(14:0(3-OH)/14:0(3-OH))	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037576	PG(14:0(3-OH)/19:iso)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037581	PG(14:0(3-OH)/14:0)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037660	PG(14:0(3-OH)/15:0)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037698	PG(14:0(3-OH)/15:0cyclo)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037777	PG(14:0(3-OH)/16:0)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037852	PG(14:0(3-OH)/16:1(9Z))	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037902	PG(14:0(3-OH)/17:0cycw7c)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0037982	PG(14:0(3-OH)/18:1(9Z))	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0038030	PG(14:0(3-OH)/19:0cycv8c)	3-Hydroxymyristate	Not Available		RHEA	34755880
MMDBr0038910	3-Hydroxytetradecanoyl-CoA	3-Hydroxymyristate	Thioesterase TesA	Hydrolysis	RHEA	34755880
MMDBr0039516	DG(14:0(3-OH)/12:0(3-OH)/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039517	DG(14:0(3-OH)/12:0/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039518	DG(14:0(3-OH)/14:0(3-OH)/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039519	DG(14:0(3-OH)/14:0/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039520	DG(14:0(3-OH)/16:0/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039521	DG(14:0(3-OH)/16:1(9Z)/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039522	DG(14:0(3-OH)/17:0cycw7c/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039523	DG(19:iso/14:0(3-OH)/0:0)	3-Hydroxymyristate	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880

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
Bacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

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

HMDB0061656

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-12808

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16064

PDB ID

Not Available

ChEBI ID

85148

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Hydroxymyristate (MMDBc0000709)

MOL for #<Metabolite:0x000055c79c6eee48>

3D MOL for #<Metabolite:0x000055c79c6eee48>

3D SDF for #<Metabolite:0x000055c79c6eee48>

3D-SDF for #<Metabolite:0x000055c79c6eee48>

PDB for #<Metabolite:0x000055c79c6eee48>

3D PDB for #<Metabolite:0x000055c79c6eee48>

SMILES for #<Metabolite:0x000055c79c6eee48>

INCHI for #<Metabolite:0x000055c79c6eee48>

Structure for #<Metabolite:0x000055c79c6eee48>

3D Structure for #<Metabolite:0x000055c79c6eee48>