ChemFOnt: Showing chemical card for Lipoyllysine (CFc000008149)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:48 UTC

Chemfont ID

CFc000008149

Molecule Identification

Common Name

Lipoyllysine

Definition

lipollysine is an important lipoic acid derivative. Most alpha-lipoic acid in food is derived from lipoamide-containing enzymes and is bound to the amino acid, lysine (lipoyllysine). Animal tissues that are rich in lipoyllysine include kidney, heart, and liver, while plant sources that are rich in lipoyllysine include spinach, broccoli, and tomatoes. Somewhat lower amounts of lipoyllysine have been measured in peas, brussel sprouts, and rice bran. Lipoic acid can be found in many common foods such as potatoes, carrots, broccoli, yeasts, beets, yams, and red meat. Dietary sources of ALA include flaxseeds, flaxseed oil, canola (rapeseed) oil, soybeans and soybean oil, pumpkin seeds and pumpkin seed oil, purslane, perilla seed oil, walnuts and walnut oil. The best food sources of lipoic acid are believed to be those foods rich in mitochondria - red meat (skeletal muscle, heart, liver, kidney). Other sources are yeast, spinach, and broccoli. Lypoyllysine is involved in Lipoate metabolism pathway where lipoyllysine is undergo hydrolysis to produce liporate and l-lysine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DL-Lipoyl-L-lysine	HMDB
Lipoyl-N-epsilon-lysine	HMDB
mono-1,2-Dithiolane-3-pentanoate	HMDB
mono-1,2-Dithiolane-3-pentanoate-L-lysine	HMDB
mono-1,2-Dithiolane-3-pentanoic acid	HMDB
(2R)-2-Amino-6-{[5-(1,2-dithiolan-3-yl)-1-hydroxypentylidene]amino}hexanoate	Generator
Lipoyllysine	MeSH

Chemical Formula

C₁₄H₂₆N₂O₃S₂

Average Molecular Weight

334.498

Monoisotopic Molecular Weight

334.138484088

IUPAC Name

(2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

Traditional Name

(2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

CAS Registry Number

20902-53-8

SMILES

N[C@H](CCCCNC(=O)CCCCC1CCSS1)C(O)=O

InChI Identifier

InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)/t11?,12-/m1/s1

InChI Key

COTIXRRJLCSLLS-PIJUOVFKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoamides

Direct Parent

Lipoamides

Alternative Parents

Substituents

Lipoamide
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Medium-chain fatty acid
Heterocyclic fatty acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
1,2-dithiolane
Amino acid or derivatives
Carboxamide group
Amino acid
Organic disulfide
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0012996)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-0.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.24	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	88.98 m³·mol⁻¹	ChemAxon
Polarizability	36.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012996

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029239

KNApSAcK ID

Not Available

Chemspider ID

35032557

KEGG Compound ID

Not Available

BioCyc ID

Protein-6-N-lipoyl-lysine

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481572

PDB ID

Not Available

ChEBI ID

175262

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Lipoyllysine (CFc000008149)

MOL for CFc000008149 (Lipoyllysine)

3D MOL for CFc000008149 (Lipoyllysine)

3D SDF for CFc000008149 (Lipoyllysine)

3D-SDF for CFc000008149 (Lipoyllysine)

PDB for CFc000008149 (Lipoyllysine)

3D PDB for CFc000008149 (Lipoyllysine)

SMILES for CFc000008149 (Lipoyllysine)

INCHI for CFc000008149 (Lipoyllysine)

Structure for CFc000008149 (Lipoyllysine)

3D Structure for CFc000008149 (Lipoyllysine)