Compound details

(R)-lipoic acid

Compound ID	CDAMM00461
Common name	(R)-lipoic acid
IUPAC name	5-(dithiolan-3-yl)pentanoic acid
Molecular formula	C₈H₁₄O₂S₂

Experimental data

Retention time	7.85
Adduct	[M+H]+
Actual mz	207.054
Theoretical mz	207.051
Error	12.19
Ionizaton mode	Positive
Instrument type	LC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score	8.7312

Identifiers and class information

Inchi key	AGBQKNBQESQNJD-JLDDOWRYNA-N
Smiles	O=C(O)CCCCC1SSCC1
Superclass	Organoheterocyclic compounds
Class	Dithiolanes

Plant source

Piper longum L.

Cinnamomum verum J. Presl

External sources

HMDB ID	HMDB0001451
KNApSAcK ID	C00000754
FooDB ID	FDB004339
DrugBank ID	DB00166
ChEBI ID	CHEBI:16494
Pubchem Compound ID	864
PlantCyc ID	LIPOIC-ACID
UNPD ID	UNPD59548
Coconut ID	CNP0120491
LipidMAPS ID	LMFA01130001
NANPDB ID

Pharmacokinetic properties

Number of descriptor values(#stars)	1
Number of non-conjugated amine groups (#amine)	0
Number of amidine and guanidine groups (#amidine)	0
Number of carboxylic acid groups (#acid)	1
Number of non-conjugated amide groups (#amide)	0
Number of rotatable bonds (#rotor)	5
Number of reactive functional groups (#rtvFG)	1
Predicted central nervous system activity (CNS)	-1
Molecular weight (mol_MW)	206.317
Computed dipole moment(dipole)	3.643
Total solvent accessible surface area (SASA)	438.833
Hydrophobic component of SASA (FOSA)	234.278
Hydrophilic component of SASA (FISA)	108.607
Pie component of the SASA (PISA)	0
Weakly polar component of the SASA (WPSA)	95.947
Total solvent accesible volume (volume)	708.376
Number of hydrogen bond donors (donorHB)	1
Number of hydrogen bond acceptors (accptHB)	3
Free energy of solvation of dipole (dip^2/V)	0.0187357
Index of cohesive interaction in solids (ACxDN^.5/SA)	0.0068363
Globularity descriptor (glob)	0.87574
Predicted polarizability in cubic angstroms (QPpolrz)	18.985
Predicted hexadecane/gas partition coefficient (QPlogPC16)	6.385
Predicted octanol/gas partition coefficient (QPlogPoct)	9.163
Predicted water/gas partition coefficient (QPlogPw)	4.864
Predicted octanol/water partition coefficient (QPlogPo/w)	2.589
Predicted aqueous solubility (QPlogS)	-2.848
Conformation-independent predicted aqueous solubility (CIQPlogS)	-2.319
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)	-1.735
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)	234.195
Predicted brain/blood partition coefficient (QPlogBB)	-0.447
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)	439.515
Predicted skin permeability, log Kp (QPlogKp)	-3.041
PM3 calculated ionization potential (IP(ev))	9.074
PM3 calculated electron affinity (EA(eV))	2.106
Number of likely metabolic reactions (#metab)	1
Prediction of binding to human serum albumin (QPlogKhsa)	-0.39
Predicted qualitative human oral absorption (HumanOralAbsorption)	3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)	84.515
Solvent-accessible surface area of fluorine atoms (SAFluorine)	0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)	0
Van der Waals surface area (PSA)	51.068
Number of nitrogen and oxygen atoms (#NandO)	2
Number of violations of Lipinski’s rule of five (RuleOfFive)	0
Number of violations of Jorgensen’s rule of three (RuleOfThree)	0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID	Gene name	Target name	TTD_ID	Prediction source
P22303	ACHE	Acetylcholinesterase	T30082	SwissTargetPrediction and SEA
O75899	GABBR2	GABA-B receptor	T42446	SEA
P48066	SLC6A11	GABA transporter 3	T38200	SEA
O75899	GABBR2	GABA-B receptor	T42446	SEA
Q4U2R8	SLC22A6	Solute carrier family 22 member 6 (by homology)	T70680	SEA
P31213	SRD5A2	Steroid 5-alpha-reductase 2	T71390	SwissTargetPrediction
P15121	AKR1B1	Aldose reductase	T26623	SwissTargetPrediction
P10145	CXCL8	Interleukin-8	T22658	SwissTargetPrediction
Q5T7T8	COX1	Prostaglandin G/H synthase 1	T60529	SwissTargetPrediction
P35354	PTGS2	Cyclooxygenase-2	T66665	SwissTargetPrediction
P42330	AKR1C3	Aldo-keto-reductase family 1 member C3	T60857	SwissTargetPrediction
P53985	SLC16A1	Monocarboxylate transporter 1 (by homology)	T95842	SwissTargetPrediction
O15229	KMO	Kynurenine 3-monooxygenase	T50973	SwissTargetPrediction
P18405	SRD5A1	Steroid 5-alpha-reductase 1	T70309	SwissTargetPrediction
P17706	PTPN2	T-cell protein-tyrosine phosphatase	T49156	SEA
Q04609	FOLH1	Glutamate carboxypeptidase II	T97071	SwissTargetPrediction
P37231	PPARG	Peroxisome proliferator-activated receptor gamma	T58921	SwissTargetPrediction
P43116	PTGER2	Prostanoid EP2 receptor	T38529	SwissTargetPrediction
Q96S37	SLC22A12	Solute carrier family 22 member 12	T86057	SwissTargetPrediction
Q9Y5Y4	PTGDR2	G protein-coupled receptor 44	T61722	SwissTargetPrediction
P53779	MAPK10	c-Jun N-terminal kinase 3	T85421	SwissTargetPrediction
P43115	PTGER3	Prostanoid EP3 receptor	T85467	SwissTargetPrediction
Q13258	PTGDR	Prostanoid DP receptor	T68782	SwissTargetPrediction
P24557	TBXAS1	Thromboxane-A synthase	T78356	SwissTargetPrediction
Q8TDS5	OXER1	Oxoeicosanoid receptor 1	T68834	SEA
Q4U2R8	SLC22A6	Solute carrier family 22 member 6 (by homology)	T70680	SEA
Q9UN88	GABRQ	GABA(A) receptor theta	T15161	SEA
P78329	CYP4F2	Cytochrome P450 4f	T82604	SEA
O60603	TLR2	Toll-like receptor 2	T82078	SEA

Target associated diseases

TTD_ID	Disease_ID	Disease name	ICD_11	Uniprot ID	Gene names
T30082	DI0025	Alzheimer disease	[ICD-11: 8A20]	P22303	ACHE
T30082	DI0166	Glaucoma	[ICD-11: 9C61]	P22303	ACHE
T30082	DI0282	Myasthenia gravis	[ICD-11: 8C6Y]	P22303	ACHE
T30082	DI0313	Oesophageal/gastroduodenal disorder	[ICD-11: DD90]	P22303	ACHE
T30082	DI0332	Pediculosis	[ICD-11: 1G00]	P22303	ACHE
T30082	DI0421	Unspecific substance harmful effect	[ICD-11: NE6Z]	P22303	ACHE
T42446	DI0117	Depression	[ICD-11: 6A70-6A7Z]	O75899	GABBR2
T42446	DI0134	Epilepsy/seizure	[ICD-11: 8A61-8A6Z]	O75899	GABBR2
T42446	DI0275	Multiple sclerosis	[ICD-11: 8A40]	O75899	GABBR2
T42446	DI0290	Narcolepsy	[ICD-11: 7A20]	O75899	GABBR2
T38200	DI0207	Indeterminate colitis	[ICD-11: DD72]	P48066	SLC6A11
T42446	DI0117	Depression	[ICD-11: 6A70-6A7Z]	O75899	GABBR2
T42446	DI0134	Epilepsy/seizure	[ICD-11: 8A61-8A6Z]	O75899	GABBR2
T42446	DI0275	Multiple sclerosis	[ICD-11: 8A40]	O75899	GABBR2
T42446	DI0290	Narcolepsy	[ICD-11: 7A20]	O75899	GABBR2
T70680	DI0167	Gout	[ICD-11: FA25]	Q4U2R8	SLC22A6
T70680	DI0206	Inborn purine/pyrimidine/nucleotide metabolism error	[ICD-11: 5C55]	Q4U2R8	SLC22A6
T70680	DI0310	Ocular disease	[ICD-11: N.A.]	Q4U2R8	SLC22A6
T71390	DI0348	Prostate hyperplasia	[ICD-11: GA90]	P31213	SRD5A2
T26623	DI0298	Neuropathy	[ICD-11: 8C0Z]	P15121	AKR1B1
T26623	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P15121	AKR1B1
T22658	DI0324	Pain	[ICD-11: MG30-MG3Z]	P10145	CXCL8
T60529	DI0141	Eye anterior segment structural developmental anomaly	[ICD-11: LA11]	Q5T7T8	COX1
T60529	DI0145	Female pelvic pain	[ICD-11: GA34]	Q5T7T8	COX1
T60529	DI0188	Hyper-lipoproteinaemia	[ICD-11: 5C80]	Q5T7T8	COX1
T60529	DI0207	Indeterminate colitis	[ICD-11: DD72]	Q5T7T8	COX1
T60529	DI0306	Nutritional deficiency	[ICD-11: 5B50-5B71]	Q5T7T8	COX1
T60529	DI0320	Osteoarthritis	[ICD-11: FA00-FA05]	Q5T7T8	COX1
T60529	DI0324	Pain	[ICD-11: MG30-MG3Z]	Q5T7T8	COX1
T60529	DI0339	Postoperative inflammation	[ICD-11: 1A00-CA43]	Q5T7T8	COX1
T60529	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	Q5T7T8	COX1
T60529	DI0372	Seborrhoeic dermatitis	[ICD-11: EA81]	Q5T7T8	COX1
T60529	DI0416	Tuberculosis	[ICD-11: 1B10-1B12]	Q5T7T8	COX1
T60529	DI0419	Ulcerative colitis	[ICD-11: DD71]	Q5T7T8	COX1
T66665	DI0087	Chronic pain	[ICD-11: MG30]	P35354	PTGS2
T66665	DI0145	Female pelvic pain	[ICD-11: GA34]	P35354	PTGS2
T66665	DI0188	Hyper-lipoproteinaemia	[ICD-11: 5C80]	P35354	PTGS2
T66665	DI0207	Indeterminate colitis	[ICD-11: DD72]	P35354	PTGS2
T66665	DI0227	Knee osteoarthritis	[ICD-11: FA01]	P35354	PTGS2
T66665	DI0320	Osteoarthritis	[ICD-11: FA00-FA05]	P35354	PTGS2
T66665	DI0324	Pain	[ICD-11: MG30-MG3Z]	P35354	PTGS2
T66665	DI0366	Rheumatoid arthritis	[ICD-11: FA20]	P35354	PTGS2
T66665	DI0416	Tuberculosis	[ICD-11: 1B10-1B12]	P35354	PTGS2
T60857	DI0145	Female pelvic pain	[ICD-11: GA34]	P42330	AKR1C3
T70309	DI0347	Prostate disease	[ICD-11: GA91]	P18405	SRD5A1
T49156	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P17706	PTPN2
T97071	DI0122	Diagnostic imaging	[ICD-11: N.A.]	Q04609	FOLH1
T97071	DI0346	Prostate cancer	[ICD-11: 2C82]	Q04609	FOLH1
T58921	DI0009	Acute diabete complication	[ICD-11: 5A2Y]	P37231	PPARG
T58921	DI0025	Alzheimer disease	[ICD-11: 8A20]	P37231	PPARG
T58921	DI0417	Type 2 diabetes mellitus	[ICD-11: 5A11]	P37231	PPARG
T38529	DI0003	Abortion	[ICD-11: JA00]	P43116	PTGER2
T38529	DI0102	Coronary atherosclerosis	[ICD-11: BA52]	P43116	PTGER2
T38529	DI0121	Diabetic foot ulcer	[ICD-11: BD54]	P43116	PTGER2
T38529	DI0166	Glaucoma	[ICD-11: 9C61]	P43116	PTGER2
T38529	DI0356	Pulmonary hypertension	[ICD-11: BB01]	P43116	PTGER2
T38529	DI0378	Sexual dysfunction	[ICD-11: HA00-HA01]	P43116	PTGER2
T38529	DI0413	Transplant rejection	[ICD-11: NE84]	P43116	PTGER2
T86057	DI0206	Inborn purine/pyrimidine/nucleotide metabolism error	[ICD-11: 5C55]	Q96S37	SLC22A12
T61722	DI0102	Coronary atherosclerosis	[ICD-11: BA52]	Q9Y5Y4	PTGDR2
T85421	DI0125	Dissociative neurological symptom disorder	[ICD-11: 6B60]	P53779	MAPK10
T85467	DI0166	Glaucoma	[ICD-11: 9C61]	P43115	PTGER3
T85467	DI0391	Solid tumour/cancer	[ICD-11: 2A00-2F9Z]	P43115	PTGER3
T85467	DI0414	Transplanted organ/tissue	[ICD-11: QB63]	P43115	PTGER3
T68782	DI0102	Coronary atherosclerosis	[ICD-11: BA52]	Q13258	PTGDR
T78356	DI0030	Angina pectoris	[ICD-11: BA40]	P24557	TBXAS1
T70680	DI0167	Gout	[ICD-11: FA25]	Q4U2R8	SLC22A6
T70680	DI0206	Inborn purine/pyrimidine/nucleotide metabolism error	[ICD-11: 5C55]	Q4U2R8	SLC22A6
T70680	DI0310	Ocular disease	[ICD-11: N.A.]	Q4U2R8	SLC22A6
T82078	DI0346	Prostate cancer	[ICD-11: 2C82]	O60603	TLR2