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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:21:04 UTC

Update Date

2023-02-21 17:17:44 UTC

HMDB ID

HMDB0012210

Secondary Accession Numbers

HMDB12210

Metabolite Identification

Common Name

Dihydrolipoate

Description

Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.087 -15.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.426 -16.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.770 -16.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.765 -15.578   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.093 -16.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.754 -15.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.431 -15.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.093 -16.356   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.432 -15.595   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.084 -17.896   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       6.416 -16.339   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0      10.431 -14.033   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    7    6                                                       
CONECT    6    5   11                                                       
CONECT    7    3    5   12                                                  
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0012210
HETATM    1  O1  UNL     1       3.264   0.680  -1.360  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.812   0.816  -0.245  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.979   1.592  -0.093  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.273   0.174   0.971  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.022  -0.615   0.757  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.863   0.190   0.241  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.363  -0.716   0.061  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.538   0.066  -0.454  1.00  0.00           C  
HETATM    9  S1  UNL     1      -1.954   1.382   0.726  1.00  0.00           S  
HETATM   10  C7  UNL     1      -2.728  -0.829  -0.599  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.945  -0.102  -1.115  1.00  0.00           C  
HETATM   12  S2  UNL     1      -4.437   1.243  -0.002  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.783   1.461  -0.684  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.051  -0.521   1.381  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.142   0.951   1.778  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.282  -1.457   0.064  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.695  -1.100   1.700  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.051   0.722  -0.705  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.539   0.961   0.971  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.143  -1.541  -0.640  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.649  -1.166   1.032  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.311   0.490  -1.461  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.931   2.356   0.620  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.961  -1.322   0.356  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.523  -1.650  -1.342  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.787  -0.824  -1.130  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.740   0.345  -2.108  1.00  0.00           H  
HETATM   28  H16 UNL     1      -4.747   0.760   1.280  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,8-Bis-sulfanyloctanoic acid	ChEBI
6,8-Dihydrothioctic acid	ChEBI
6,8-Dimercapto-octanoic acid	ChEBI
6,8-Dimercaptooctanoic acid	ChEBI
DHLA	ChEBI
Dihydro-alpha-lipoic acid	ChEBI
Dihydro-lipoic acid	ChEBI
Dihydrothioctic acid	ChEBI
Dihydrolipoic acid	Kegg
6,8-Bis-sulfanyloctanoate	Generator
6,8-Bis-sulphanyloctanoate	Generator
6,8-Bis-sulphanyloctanoic acid	Generator
6,8-Dihydrothioctate	Generator
6,8-Dimercapto-octanoate	Generator
6,8-Dimercaptooctanoate	Generator
Dihydro-a-lipoate	Generator
Dihydro-a-lipoic acid	Generator
Dihydro-alpha-lipoate	Generator
Dihydro-α-lipoate	Generator
Dihydro-α-lipoic acid	Generator
Dihydro-lipoate	Generator
Dihydrothioctate	Generator
6,8-Disulfanyloctanoate	HMDB
6,8-Disulfanyloctanoic acid	HMDB
D,L-Dihydrolipoate	HMDB
D,L-Dihydrolipoic acid	HMDB
dihydro-DL-alpha-Lipoate	HMDB
dihydro-DL-alpha-Lipoic acid	HMDB
dihydro-Thioctic acid	HMDB
dihydro-Thiocytic acid	HMDB
DL-dihydro-a-6-Thioctic acid	HMDB
DL-dihydro-alpha-6-Thioctic acid	HMDB
Reduced DL-6,8-thioctic acid	HMDB
Reduced lipoate	HMDB
Reduced lipoic acid	HMDB
Reduced thioctic acid	HMDB
Dihydrolipoic acid, (+-)-isomer	MeSH, HMDB
Dihydrolipoic acid, sodium salt	MeSH, HMDB

Chemical Formula

C₈H₁₆O₂S₂

Average Molecular Weight

208.341

Monoisotopic Molecular Weight

208.059171136

IUPAC Name

6,8-disulfanyloctanoic acid

Traditional Name

dihydrolipoic acid

CAS Registry Number

462-20-4

SMILES

OC(=O)CCCCC(S)CCS

InChI Identifier

InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

InChI Key

IZFHEQBZOYJLPK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Thia fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thio-fatty acid (CHEBI:18047 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.91	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	55.94 m³·mol⁻¹	ChemAxon
Polarizability	23.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.175	31661259
DarkChem	[M-H]-	142.316	31661259
DeepCCS	[M+H]+	147.247	30932474
DeepCCS	[M-H]-	144.765	30932474
DeepCCS	[M-2H]-	180.349	30932474
DeepCCS	[M+Na]+	155.579	30932474
AllCCS	[M+H]+	145.2	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	148.5	32859911
AllCCS	[M+Na]+	149.4	32859911
AllCCS	[M-H]-	150.6	32859911
AllCCS	[M+Na-2H]-	152.5	32859911
AllCCS	[M+HCOO]-	154.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.84 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5596 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2671.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	445.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	276.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	581.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	701.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	436.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1217.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	374.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1397.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	593.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	193.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrolipoate	OC(=O)CCCCC(S)CCS	3224.6	Standard polar	33892256
Dihydrolipoate	OC(=O)CCCCC(S)CCS	1676.0	Standard non polar	33892256
Dihydrolipoate	OC(=O)CCCCC(S)CCS	1814.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrolipoate,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(S)CCS	1917.3	Semi standard non polar	33892256
Dihydrolipoate,1TMS,isomer #2	C[Si](C)(C)SC(CCS)CCCCC(=O)O	1978.8	Semi standard non polar	33892256
Dihydrolipoate,1TMS,isomer #3	C[Si](C)(C)SCCC(S)CCCCC(=O)O	2027.9	Semi standard non polar	33892256
Dihydrolipoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C	1994.1	Semi standard non polar	33892256
Dihydrolipoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C	2009.5	Standard non polar	33892256
Dihydrolipoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C	2285.5	Standard polar	33892256
Dihydrolipoate,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C	2052.5	Semi standard non polar	33892256
Dihydrolipoate,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C	2010.4	Standard non polar	33892256
Dihydrolipoate,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C	2389.1	Standard polar	33892256
Dihydrolipoate,2TMS,isomer #3	C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C	2127.0	Semi standard non polar	33892256
Dihydrolipoate,2TMS,isomer #3	C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C	2129.4	Standard non polar	33892256
Dihydrolipoate,2TMS,isomer #3	C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C	2490.6	Standard polar	33892256
Dihydrolipoate,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2171.9	Semi standard non polar	33892256
Dihydrolipoate,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2206.3	Standard non polar	33892256
Dihydrolipoate,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2193.5	Standard polar	33892256
Dihydrolipoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS	2139.8	Semi standard non polar	33892256
Dihydrolipoate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SC(CCS)CCCCC(=O)O	2211.1	Semi standard non polar	33892256
Dihydrolipoate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCCC(S)CCCCC(=O)O	2264.2	Semi standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2501.6	Semi standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2446.5	Standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2477.7	Standard polar	33892256
Dihydrolipoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2563.6	Semi standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2451.7	Standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2576.3	Standard polar	33892256
Dihydrolipoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C	2647.4	Semi standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C	2558.9	Standard non polar	33892256
Dihydrolipoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C	2588.8	Standard polar	33892256
Dihydrolipoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2898.9	Semi standard non polar	33892256
Dihydrolipoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2816.2	Standard non polar	33892256
Dihydrolipoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2522.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dihydrolipoate GC-EI-TOF (Non-derivatized)	splash10-0007-5920000000-99648df42c67f7327a1d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrolipoate GC-EI-TOF (Non-derivatized)	splash10-0007-5920000000-99648df42c67f7327a1d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kij-5900000000-7564ff734a37b263a7ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrolipoate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9520000000-35f52ace937d40f6ba6e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOF	splash10-00di-0900000000-832657635f2c81515eac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOF	splash10-00di-1900000000-832657635f2c81515eac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOF	splash10-0ab9-0690000000-bb3d2691ed5ceb749b8c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Positive-QTOF	splash10-0a4l-0920000000-203769a6e5514dfdacce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOF	splash10-0bvl-0900000000-e0d6ca4b105aaeae3f10	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Positive-QTOF	splash10-06vi-9500000000-30fa7bade921a70952d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOF	splash10-0ab9-0960000000-352daa80c3d73329d4b8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOF	splash10-0a4i-1930000000-dee930722526f680e10d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Negative-QTOF	splash10-053r-9300000000-c53948709f447f46266c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Positive-QTOF	splash10-0a4i-0930000000-266230745999efddf6dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOF	splash10-0ufr-2900000000-24ea3b6c12cfdd8e2cac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Positive-QTOF	splash10-0006-9300000000-a87ea4acfc88c77960a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOF	splash10-0a4i-0190000000-212b987ce9dfd82aaeb6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOF	splash10-0a4r-3920000000-1948f3bf848db6d6ef45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Negative-QTOF	splash10-001l-9400000000-39e9224d6c07b378fb5a	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nitrogen metabolism	Not Available
Glycine, serine and threonine metabolism	Not Available
Dimethylglycine Dehydrogenase Deficiency		Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)		Not Available
Sarcosinemia		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028855

KNApSAcK ID

Not Available

Chemspider ID

408

KEGG Compound ID

C02147

BioCyc ID

6-S-ACETYL-DIHYDROLIPOATE

BiGG ID

Not Available

Wikipedia Link

Dihydrolipoic_acid

METLIN ID

Not Available

PubChem Compound

421

PDB ID

Not Available

ChEBI ID

18047

Food Biomarker Ontology

Not Available

VMH ID

C02147

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Prehn JH, Karkoutly C, Nuglisch J, Peruche B, Krieglstein J: Dihydrolipoate reduces neuronal injury after cerebral ischemia. J Cereb Blood Flow Metab. 1992 Jan;12(1):78-87. [PubMed:1345759 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dihydrolipoate (HMDB0012210)

MOL for HMDB0012210 (Dihydrolipoate)

3D MOL for HMDB0012210 (Dihydrolipoate)

3D SDF for HMDB0012210 (Dihydrolipoate)

3D-SDF for HMDB0012210 (Dihydrolipoate)

PDB for HMDB0012210 (Dihydrolipoate)

3D PDB for HMDB0012210 (Dihydrolipoate)

SMILES for HMDB0012210 (Dihydrolipoate)

INCHI for HMDB0012210 (Dihydrolipoate)

Structure for HMDB0012210 (Dihydrolipoate)

3D Structure for HMDB0012210 (Dihydrolipoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra