Milk Composition Database: Showing metabocard for Phytanic acid (BMDB0000801)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:46 UTC

Update Date

2020-05-21 16:28:37 UTC

MCDB ID

BMDB0000801

Secondary Accession Numbers

BMDB00801

Metabolite Identification

Common Name

Phytanic acid

Description

Phytanic acid, also known as phytanate or acid, phytanic, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Phytanic acid is possibly soluble (in water) and a very weakly acidic compound (based on its pKa). In cattle, phytanic acid is involved in the metabolic pathway called the phytanic Acid peroxisomal oxidation pathway. Phytanic acid is a potentially toxic compound. Phytanic acid has been found to be associated with several diseases known as cerebrotendinous xanthomatosis, rhizomelic chondrodysplasia punctata, and pseudoneonatal adrenoleukodystrophy; also phytanic acid has been linked to several inborn metabolic disorders including adrenoleukodystrophy and peroxisomal biogenesis defect.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,7,11,15-Tetramethyl hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecansaeure	ChEBI
3,7,11,15-Tetramethylhexadecanoic acid	Kegg
3,7,11,15-Tetramethyl hexadecanoate	Generator
3,7,11,15-Tetramethyl-hexadecanoate	Generator
3,7,11,15-Tetramethylhexadecanoate	Generator
Phytanate	Generator
3,7,11,15-Tetramethylhexadecoanoate	HMDB
3,7,11,15-Tetramethylhexadecoanoic acid	HMDB
Phytanoate	HMDB
Phytanoic acid	HMDB
Acid, phytanic	HMDB

Chemical Formula

C₂₀H₄₀O₂

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

IUPAC Name

3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

phytanic acid

CAS Registry Number

14721-66-5

SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O

InChI Identifier

InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

InChI Key

RLCKHJSFHOZMDR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:16285 )
branched-chain saturated fatty acid (CHEBI:16285 )
methyl-branched fatty acid (CHEBI:16285 )
Acyclic diterpenoids (C01607 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.28	ALOGPS
logP	7.4	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	5.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	41.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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	splash10-0006-9780000000-d08f456f5acb304b7ea2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9443000000-5bbc79ddca11ee15c346	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0009000000-1344b5ce122597753d72	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00e9-9000000000-d058ed1cd7bf2496d801	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01b9-9000000000-b91cf96bf3e1ed9907c9	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0192000000-404c7c552fbd445291f4	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00mk-4790000000-c4c72f2a0388e83c4d50	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9720000000-e2429e81001f3469126a	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0089000000-e67aa3a53cb223588ace	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02tc-1094000000-c8ba97412b0185f5a5b3	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-8590000000-02e2e52e9c0e6f20a064	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-849ba1e3311607445182	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-1d86a3df25ae3d6f62b5	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-8393000000-8564c0781362b5ca2da4	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4569000000-0ae84af33d4a6cee1563	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06y9-9720000000-8d0e05ef1818d392c4fb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-19bc307031b7da7b3414	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 14168161	details

External Links

HMDB ID

HMDB0000801

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022252

KNApSAcK ID

Not Available

Chemspider ID

25001

KEGG Compound ID

C01607

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16285

References

Synthesis Reference

Karrer, P.; Epprecht, A.; Konig, Hans. General method of preparation for 2-methyl-3-alkylnaphthoquinones. Constitution and vitamin K activity. Helvetica Chimica Acta (1940), 23 272-83.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]

Showing metabocard for Phytanic acid (BMDB0000801)

Structure for BMDB0000801 (Phytanic acid)