Milk Composition Database: Showing metabocard for Heneicosanoic acid (BMDB0002345)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:54:22 UTC

Update Date

2020-04-22 15:10:43 UTC

MCDB ID

BMDB0002345

Secondary Accession Numbers

BMDB02345

Metabolite Identification

Common Name

Heneicosanoic acid

Description

Heneicosanoic acid, also known as N-heneicosanoate or 21:0, 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. Heneicosanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Heneicosanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
21:0	ChEBI
C21:0	ChEBI
Heneicosansaeure	ChEBI
Heneicosylic acid	ChEBI
N-Heneicosanoic acid	ChEBI
N-Heneicosylic acid	ChEBI
N-Henicosanoic acid	ChEBI
Heneicosylate	Generator
N-Heneicosanoate	Generator
N-Heneicosylate	Generator
N-Henicosanoate	Generator
Heneicosanoate	Generator
Heneicosanate	HMDB
Heneicosanic acid	HMDB
Henicosanoate	HMDB
Henicosanoic acid	HMDB
Heneicosanoic acid	ChEBI
FA(21:0)	PhytoBank

Chemical Formula

C₂₁H₄₂O₂

Average Molecular Weight

326.557

Monoisotopic Molecular Weight

326.318480588

IUPAC Name

henicosanoic acid

Traditional Name

heneicosanoic acid

CAS Registry Number

2363-71-5

SMILES

CCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C21H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23/h2-20H2,1H3,(H,22,23)

InChI Key

CKDDRHZIAZRDBW-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
Straight chain 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:39248 )
straight-chain saturated fatty acid (CHEBI:39248 )
Straight chain fatty acids (LMFA01010021 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	74 - 76 °C	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	8.97	ALOGPS
logP	8.48	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	4.95	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	19	ChemAxon
Refractivity	100.09 m³·mol⁻¹	ChemAxon
Polarizability	45.09 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
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2900000000-d29fc7eb4fea54b3bffe	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900000000-d29fc7eb4fea54b3bffe	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9680000000-c0721d1f1430583b0cfe	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9551000000-56b944394c02259484e5	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-0009000000-76ddc619babd8e5695ce	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-004i-0009000000-673b532d7cf4b18b12a9	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-001i-0090000000-c40174e878425a9d0507	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-004i-0009000000-de3d68bcc91dd21e1b82	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0009000000-b460efbbb047c9d921a0	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0009000000-50c83801cda9cc618562	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0009000000-692538bbbc86d3d2a008	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0912000000-73d16aa01cbd339c9d92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0009000000-de3d68bcc91dd21e1b82	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0009000000-b460efbbb047c9d921a0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0009000000-50c83801cda9cc618562	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0009000000-692538bbbc86d3d2a008	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0973-0691000000-216228016fee98acf869	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0009000000-400faab343cdd1639a7c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0009000000-de3d68bcc91dd21e1b82	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0029000000-8ed29c4b9b431c1b2551	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0arr-2493000000-28f328152d5c63740471	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-6970000000-ea3835b108a78f89fab7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-7ddcca4730bc179bc0c2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1039000000-18ffc404f0bfd0d60921	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9130000000-d9a208c7e92c239a22b4	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05dl-9201000000-365f2ad065e0036dda86	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	PMID: 19038946	details
Detected but not Quantified	Not Applicable	PMID: 14168161	details

External Links

HMDB ID

HMDB0002345

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002742

KNApSAcK ID

C00053301

Chemspider ID

16012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Heneicosylic acid

METLIN ID

4208

PubChem Compound

16898

PDB ID

Not Available

ChEBI ID

39248

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]

Showing metabocard for Heneicosanoic acid (BMDB0002345)

Structure for BMDB0002345 (Heneicosanoic acid)