P. aeruginosa Metabolome Database: lipoamide (PAMDB110217)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110217

Identification

Name:

lipoamide

Description:

A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5-(1,2-dithiolan-3-yl)-pentanamide
DL-lipoamide
6,8-dithiooctanoic amide

Chemical Formula:

C₈H₁₅NOS₂

Average Molecular Weight:

205.33

Monoisotopic Molecular Weight:

205.0595054888

InChI Key:

FCCDDURTIIUXBY-SSDOTTSWSA-N

InChI:

InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)/t7-/m1/s1

CAS number:

940-69-2

IUPAC Name:

5-(1,2-dithiolan-3-yl)pentanamide

Traditional IUPAC Name:

lipoamide

SMILES:

C1(CC(CCCCC(N)=O)SS1)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as lipoamides. These are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Dithiolanes

Direct Parent

Lipoamides

Alternative Parents

Substituents

Lipoamide
Fatty amide
Fatty acyl
1,2-dithiolane
Carboxamide group
Organic disulfide
Primary carboxylic acid amide
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:17460 )
dithiolanes (CHEBI:17460 )
Primary amides (LMFA08010006 )
a small molecule (LIPOAMIDE )

Physical Properties

State:

Solid

Charge:

Melting point:

126.0 - 129.0 °C

Experimental Properties:

Property	Value	Reference
Melting Point	126.0 - 129.0 °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
Water Solubility	0.1 mg/mL	ALOGPS
logP	2.3	ALOGPS
logP	1.31	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.19 m³·mol^-1	ChemAxon
Polarizability	22.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Citric Acid Cycle pae00020
Lysine Degradation pae00310
Pyruvate Metabolism pae00620
Valine, Leucine and Isoleucine Degradation pae00280

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-6963000000-7e1887d53c2801b09961	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-017l-3920000000-a3a7a08acf06d41c9b73	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-24fca44fc025dbd6be18	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ziu-9700000000-7dfd23f450bdfd581100	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056u-9000000000-13583c4eb6b06a56c392	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-052r-2920000000-a4fb7176abf63e581f5e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-2900000000-10a079a84f024494ae23	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0zfr-9800000000-b01332176d6829b1eaa1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0udl-9400000000-7a03c741edae36dff9cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a5c-9100000000-7b44dfbfcbb0cc516254	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-50512172ce038bce2995	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-7652a33c17a37b6914aa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0udi-0900000000-0df59a6540bede8a4a79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Przybyla-Zawislak B, Gadde DM, Ducharme K, McCammon MT (1999)Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes. Genetics 152, Pubmed: 10224250
Shen W, Hao J, Feng Z, Tian C, Chen W, Packer L, Shi X, Zang W, Liu J (2011)Lipoamide or lipoic acid stimulates mitochondrial biogenesis in 3T3-L1 adipocytes via the endothelial NO synthase-cGMP-protein kinase G signalling pathway. British journal of pharmacology 162, Pubmed: 21108628
Feeney MA, Veeravalli K, Boyd D, Gon S, Faulkner MJ, Georgiou G, Beckwith J (2011)Repurposing lipoic acid changes electron flow in two important metabolic pathways of Escherichia coli. Proceedings of the National Academy of Sciences of the United States of America 108, Pubmed: 21521794

Synthesis Reference:

Xu, Yaming; Li, Zhitian; Gu, Yunlong. Synthesis of thioctamide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CAS	940-69-2
ChEBI	6491
ChemSpider	5360246
HMDB	HMDB00962
KEGG	C00248
PubChem	6992093

lipoamide (PAMDB110217)

Structure for lipoamide (PAMDB110217)