NP-MRD: Showing NP-Card for Lipoyllysine (NP0339142)

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Record Information

Version

2.0

Created at

2024-09-11 19:52:54 UTC

Updated at

2024-09-11 19:52:54 UTC

NP-MRD ID

NP0339142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lipoyllysine

Description

Lipoyllysine 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. The best food sources of lipoic acid are believed to be those foods rich in mitochondria - red meat (skeletal muscle, heart, liver, kidney). Lipoyllysine is a very strong basic compound (based on its pKa). 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. Other sources are yeast, spinach, and broccoli. Most alpha-lipoic acid in food is derived from lipoamide-containing enzymes and is bound to the amino acid, lysine (lipoyllysine). 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016482D          

 21 21  0  0  1  0            999 V2000
    8.8172  -16.0079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303  -15.4559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2149  -15.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8281  -15.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6127  -15.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2258  -14.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0104  -15.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6235  -14.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4081  -14.8196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4519  -13.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6673  -13.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4958  -12.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7112  -12.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5397  -11.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7860  -11.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8722  -10.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6792  -10.3063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0917  -11.0207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2588  -14.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8719  -14.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742  -14.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 19  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  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339142

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C14H26N2O3S2

> <MOLECULAR_WEIGHT>
334.498

> <EXACT_MASS>
334.138484088

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.78029032523753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.8170249658909206

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.876709047638645

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2426573474053453

> <JCHEM_PKA_STRONGEST_BASIC>
9.52653029055576

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
88.98099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.49e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  N   UNK     0      16.459 -29.881   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      17.603 -28.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.068 -29.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.212 -28.296   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.677 -28.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.821 -27.742   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      24.286 -28.218   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      25.431 -27.187   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      26.895 -27.663   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      25.110 -25.681   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.646 -25.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.325 -23.699   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.861 -23.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.541 -21.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.134 -21.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.295 -19.559   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      21.801 -19.238   0.000  0.00  0.00           S+0
HETATM   18  S   UNK     0      22.571 -20.572   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0      17.283 -27.345   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.428 -26.314   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      15.819 -26.869   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   14   17                                                       
CONECT   19    2   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

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 Mass

334.4980 Da

Monoisotopic Mass

334.13848 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Physical Properties

State

Not Available

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	-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

FoodDB ID

FDB029239

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lipoyllysine (NP0339142)

MOL for NP0339142 (Lipoyllysine)

3D MOL for NP0339142 (Lipoyllysine)

3D SDF for NP0339142 (Lipoyllysine)

3D-SDF for NP0339142 (Lipoyllysine)

PDB for NP0339142 (Lipoyllysine)

3D PDB for NP0339142 (Lipoyllysine)

SMILES for NP0339142 (Lipoyllysine)

INCHI for NP0339142 (Lipoyllysine)

Structure for NP0339142 (Lipoyllysine)

3D Structure for NP0339142 (Lipoyllysine)