(S)-lipoic acid (CHEBI:43796)

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CHEBI:43796 - (S)-lipoic acid

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ChEBI Name	(S)-lipoic acid

ChEBI ID	CHEBI:43796

ChEBI ASCII Name	(S)-lipoic acid

Definition	The (S)-enantiomer of lipoic acid. Not found in nature, it may exert detrimental effects on biosystems.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43790, CHEBI:30315

Supplier Information	ChemicalBook:CB7855122, eMolecules:10678602, ZINC000001532729

Download	Molfile XML SDF

more structures >>

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Marvin 05040712473D

26 26 0 0 0 0 999 V2000

-0.4729 2.6732 -0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5847 1.0886 0.6427 S 0 0 0 0 0 0 0 0 0 0 0 0

-1.2052 1.3351 -0.2695 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0

0.5505 2.5197 1.0096 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4116 3.7794 1.1100 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8704 3.4406 1.4410 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4591 4.4726 2.3844 C 0 0 0 0 0 0 0 0 0 0 0 0

4.9651 4.3043 2.5237 C 0 0 0 0 0 0 0 0 0 0 0 0

5.6000 5.5713 3.0589 C 0 0 0 0 0 0 0 0 0 0 0 0

6.7995 5.6372 3.1906 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8334 6.6611 3.3390 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2009 3.4756 0.1524 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0416 2.9331 -1.0575 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0113 1.2619 0.5009 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6743 1.2724 -1.2751 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0271 2.3636 1.9905 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3838 4.3089 0.1278 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9910 4.4472 1.8932 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9066 2.4400 1.9344 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4709 3.4086 0.5037 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2510 5.4786 1.9623 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9726 4.3764 3.3810 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1705 3.4698 3.2336 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4001 4.0517 1.5328 H 0 0 0 0 0 0 0 0 0 0 0 0

5.2436 7.4785 3.6297 H 0 0 0 0 0 0 0 0 0 0 0 0

5 1 1 0 0 0 0

5 2 1 0 0 0 0

1 3 1 0 0 0 0

2 4 1 0 0 0 0

3 4 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 1 0 0 0 0

9 10 1 0 0 0 0

10 12 1 0 0 0 0

10 11 2 0 0 0 0

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24 9 1 0 0 0 0

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26 12 1 0 0 0 0

M END): 19 ms

reading 26 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

26 atoms created

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Formula

C8H14O2S2

Net Charge

Average Mass

206.32756

Monoisotopic Mass

206.04352

InChI

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1

InChIKey

AGBQKNBQESQNJD-ZETCQYMHSA-N

SMILES

OC(=O)CCCC[C@H]1CCSS1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. (via lipoic acid )

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. (via lipoic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(S)-lipoic acid (CHEBI:43796) has functional parent octanoic acid (CHEBI:28837) (S)-lipoic acid (CHEBI:43796) is a dithiolanes (CHEBI:39192) (S)-lipoic acid (CHEBI:43796) is a heterocyclic fatty acid (CHEBI:48847) (S)-lipoic acid (CHEBI:43796) is a lipoic acid (CHEBI:16494) (S)-lipoic acid (CHEBI:43796) is a thia fatty acid (CHEBI:59643) (S)-lipoic acid (CHEBI:43796) is enantiomer of (R)-lipoic acid (CHEBI:30314)

Incoming	(R)-lipoic acid (CHEBI:30314) is enantiomer of (S)-lipoic acid (CHEBI:43796) (S)-lipoyl group (CHEBI:38233) is substituent group from (S)-lipoic acid (CHEBI:43796)

IUPAC Name

5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid

Synonyms	Sources
(S)-(−)-lipoic acid	ChEBI
(S)-1,2-dithiolane-3-pentanoic acid	ChemIDplus
(S)-alpha-lipoic acid	ChEBI
L-1,2-dithiolane 3-valeric acid	ChEBI
L-6,8-thioctic acid	ChEBI
L-6-thioctic acid	ChEBI
LIPOIC ACID	PDBeChem
S-LA	ChEBI
SLA	ChEBI
thioctic acid l-form	ChemIDplus

Manual Xrefs	Databases
HMDB0014312	HMDB
LPA	PDBeChem
View more database links

Registry Numbers	Types	Sources
1077-27-6	CAS Registry Number	ChemIDplus
81852	Beilstein Registry Number	Beilstein

Citations

Cicchillo RM, Iwig DF, Jones AD, Nesbitt NM, Baleanu-Gogonea C, Souder MG, Tu L, Booker SJ (2004)
Lipoyl synthase requires two equivalents of S-adenosyl-L-methionine to synthesize one equivalent of lipoic acid.
Biochemistry 43, 6378-6386 [PubMed:15157071]
[show Abstract]

Frölich L, Götz ME, Weinmüller M, Youdim MB, Barth N, Dirr A, Gsell W, Jellinger K, Beckmann H, Riederer P (2004)
(r)-, but not (s)-alpha lipoic acid stimulates deficient brain pyruvate dehydrogenase complex in vascular dementia, but not in Alzheimer dementia.
Journal of neural transmission (Vienna, Austria : 1996) 111, 295-310 [PubMed:14991456]
[show Abstract]

Hong YS, Jacobia SJ, Packer L, Patel MS (1999)
The inhibitory effects of lipoic compounds on mammalian pyruvate dehydrogenase complex and its catalytic components.
Free radical biology & medicine 26, 685-694 [PubMed:10218658]
[show Abstract]

Streeper RS, Henriksen EJ, Jacob S, Hokama JY, Fogt DL, Tritschler HJ (1997)
Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle.
The American journal of physiology 273, E185-91 [PubMed:9252495]
[show Abstract]

Last Modified

26 August 2014

CHEBI:43796 - (S)-lipoic acid

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