Dihydrolipoate



Compound IDCDAMM00463
Common nameDihydrolipoate
IUPAC name6,8-bis(sulfanyl)octanoic acid
Molecular formulaC8H16O2S2

Experimental data

Retention time10.12
Adduct[M+H]+
Actual mz209.067
Theoretical mz209.066
Error5.38
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score9.5369

Identifiers and class information

Inchi keyIZFHEQBZOYJLPK-UHFFFAOYNA-N
SmilesO=C(O)CCCCC(S)CCS
SuperclassLipids and lipid-like molecules
ClassFatty Acyls

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)9
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)208.333
Computed dipole moment(dipole)4.168
Total solvent accessible surface area (SASA)455.516
Hydrophobic component of SASA (FOSA)219.153
Hydrophilic component of SASA (FISA)108.487
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)127.876
Total solvent accesible volume (volume)736.877
Number of hydrogen bond donors (donorHB)2.6
Number of hydrogen bond acceptors (accptHB)3
Free energy of solvation of dipole (dip^2/V)0.023581
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0106195
Globularity descriptor (glob)0.866147
Predicted polarizability in cubic angstroms (QPpolrz)17.557
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.204
Predicted octanol/gas partition coefficient (QPlogPoct)11.059
Predicted water/gas partition coefficient (QPlogPw)6.376
Predicted octanol/water partition coefficient (QPlogPo/w)2.586
Predicted aqueous solubility (QPlogS)-2.388
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.14
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.89
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)234.811
Predicted brain/blood partition coefficient (QPlogBB)-0.629
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)659.35
Predicted skin permeability, log Kp (QPlogKp)-2.655
PM3 calculated ionization potential (IP(ev))9.272
PM3 calculated electron affinity (EA(eV))-0.233
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.609
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)84.516
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)51.107
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P00797RENReninT61622SwissTargetPrediction
P24046GABRR1GABA receptor rho-1 subunitT99665SEA
P15144ANPEPAminopeptidase NT67272SwissTargetPrediction
O75899GABBR2GABA-B receptorT42446SEA
P00734F2ThrombinT94033SwissTargetPrediction
P48066SLC6A11GABA transporter 3T38200SEA
O75899GABBR2GABA-B receptorT42446SEA
Q14833GRM4Metabotropic glutamate receptor 4T99402SwissTargetPrediction
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
Q9H3R0KDM4CLysine-specific demethylase 4CT73863SEA
P10145CXCL8Interleukin-8T22658SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SwissTargetPrediction
Q9H4A4RNPEPAminopeptidase BT57818SEA
O75164KDM4ALysine-specific demethylase 4AT18904SEA
Q96IY4CPB2Carboxypeptidase B2 isoform AT98022SwissTargetPrediction
O15229KMOKynurenine 3-monooxygenaseT50973SwissTargetPrediction
Q07075ENPEPAminopeptidase AT31956SwissTargetPrediction and SEA
P15090FABP4Fatty acid binding protein adipocyteT07217SwissTargetPrediction
Q07869PPARAPeroxisome proliferator-activated receptor alphaT86591SwissTargetPrediction
Q01469FABP5Fatty acid binding protein epidermalT21507SwissTargetPrediction
O14842FFAR1Free fatty acid receptor 1T25608SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P11473VDRVitamin D receptorT34234SwissTargetPrediction
Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
P14174MIFMacrophage migration inhibitory factorT39977SwissTargetPrediction
P27695APEX1DNA-(apurinic or apyrimidinic site) lyaseT13348SwissTargetPrediction
Q9P1W9PIM2Serine/threonine-protein kinase PIM2T07279SwissTargetPrediction
Q96S37SLC22A12Solute carrier family 22 member 12T86057SwissTargetPrediction
Q9Y5Y4PTGDR2G protein-coupled receptor 44T61722SwissTargetPrediction
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction
P0DMV8HSPA1AHeat shock 70 kDa protein 1T49639SwissTargetPrediction
P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
P25098GRK2G-protein coupled receptor kinase 2T62548SwissTargetPrediction
Q9UGN5PARP2Poly [ADP-ribose] polymerase 2T40812SwissTargetPrediction
Q9BYF1ACE2Angiotensin-converting enzyme 2T27889SwissTargetPrediction
O15382BCAT2Branched-chain-amino-acid aminotransferase, mitochondrialT94788SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
P15085CPA1Carboxypeptidase A1T33966SwissTargetPrediction
Q13258PTGDRProstanoid DP receptorT68782SwissTargetPrediction
P24557TBXAS1Thromboxane-A synthaseT78356SwissTargetPrediction
Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SwissTargetPrediction and SEA
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P68400CSNK2A1Casein kinase II alphaT51565SwissTargetPrediction
P19784CSNK2A2Casein kinase II alpha (prime)T80526SwissTargetPrediction
P14735IDEInsulin-degrading enzymeT81900SwissTargetPrediction
Q6ZMT4KDM7ALysine-specific demethylase 7A/7BT18784SEA
Q9Y3Q0NAALAD2NAALADase IIT70036SEA
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SEA
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
Q9UN88GABRQGABA(A) receptor thetaT15161SEA
P78329CYP4F2Cytochrome P450 4fT82604SEA
O60603TLR2Toll-like receptor 2T82078SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T06273DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P09874PARP1
T06273DI0143Fallopian tube cancer[ICD-11: 2C74]P09874PARP1
T06273DI0321Ovarian cancer[ICD-11: 2C73]P09874PARP1
T06273DI0334Peritoneal cancer[ICD-11: 2C51]P09874PARP1
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T61622DI0190Hypertension[ICD-11: BA00-BA04]P00797REN
T67272DI0351Psoriasis[ICD-11: EA90]P15144ANPEP
T42446DI0117Depression[ICD-11: 6A70-6A7Z]O75899GABBR2
T42446DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O75899GABBR2
T42446DI0275Multiple sclerosis[ICD-11: 8A40]O75899GABBR2
T42446DI0290Narcolepsy[ICD-11: 7A20]O75899GABBR2
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T38200DI0207Indeterminate colitis[ICD-11: DD72]P48066SLC6A11
T42446DI0117Depression[ICD-11: 6A70-6A7Z]O75899GABBR2
T42446DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O75899GABBR2
T42446DI0275Multiple sclerosis[ICD-11: 8A40]O75899GABBR2
T42446DI0290Narcolepsy[ICD-11: 7A20]O75899GABBR2
T99402DI0331Parkinsonism[ICD-11: 8A00]Q14833GRM4
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T22658DI0324Pain[ICD-11: MG30-MG3Z]P10145CXCL8
T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T98022DI0073Cerebral ischaemia[ICD-11: 8B1Z]Q96IY4CPB2
T98022DI0074Cerebral ischaemic stroke[ICD-11: 8B11]Q96IY4CPB2
T98022DI0405Thrombosis[ICD-11: DB61-GB90]Q96IY4CPB2
T31956DI0190Hypertension[ICD-11: BA00-BA04]Q07075ENPEP
T86591DI0187Hyperlipidemia[ICD-11: 5C80]Q07869PPARA
T86591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q07869PPARA
T86591DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q07869PPARA
T25608DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O14842FFAR1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T34234DI0083Chronic kidney disease[ICD-11: GB61]P11473VDR
T34234DI0171Hair/hair growth developmental defect[ICD-11: LC30]P11473VDR
T34234DI0189Hyper-parathyroidism[ICD-11: 5A51]P11473VDR
T34234DI0195Hypo-parathyroidism[ICD-11: 5A50]P11473VDR
T34234DI0266Mineral deficiency[ICD-11: 5B5K]P11473VDR
T34234DI0351Psoriasis[ICD-11: EA90]P11473VDR
T34234DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]P11473VDR
T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T39977DI0403Thrombocytopenia[ICD-11: 3B64]P14174MIF
T13348DI0365Retinopathy[ICD-11: 9B71]P27695APEX1
T13348DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P27695APEX1
T07279DI0274Multiple myeloma[ICD-11: 2A83]Q9P1W9PIM2
T07279DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9P1W9PIM2
T86057DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q96S37SLC22A12
T61722DI0102Coronary atherosclerosis[ICD-11: BA52]Q9Y5Y4PTGDR2
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
T49639DI0121Diabetic foot ulcer[ICD-11: BD54]P0DMV8HSPA1A
T49639DI0180Herpes simplex infection[ICD-11: 1F00]P0DMV8HSPA1A
T49639DI0231Leukaemia[ICD-11: 2A60-2B33]P0DMV8HSPA1A
T49639DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P0DMV8HSPA1A
T49639DI0260Metastatic malignant neoplasm[ICD-11: 2D50-2E09]P0DMV8HSPA1A
T49639DI0298Neuropathy[ICD-11: 8C0Z]P0DMV8HSPA1A
T49639DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMV8HSPA1A
T49639DI0395Stomach cancer[ICD-11: 2B72]P0DMV8HSPA1A
T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
T40812DI0321Ovarian cancer[ICD-11: 2C73]Q9UGN5PARP2
T40812DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UGN5PARP2
T27889DI0009Acute diabete complication[ICD-11: 5A2Y]Q9BYF1ACE2
T27889DI0217Intrathoracic organs injury[ICD-11: NB32]Q9BYF1ACE2
T27889DI0356Pulmonary hypertension[ICD-11: BB01]Q9BYF1ACE2
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T78356DI0030Angina pectoris[ICD-11: BA40]P24557TBXAS1
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T51565DI0104Coronavirus infection[ICD-11: 1D92]P68400CSNK2A1
T51565DI0235Liver cancer[ICD-11: 2C12]P68400CSNK2A1
T51565DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P68400CSNK2A1
T81900DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P14735IDE
T17852DI0025Alzheimer disease[ICD-11: 8A20]O76083PDE9A
T17852DI0115Dementia[ICD-11: 6D80-6D8Z]O76083PDE9A
T17852DI0165Genitourinary disease[ICD-11: GA0Z-GC8Z]O76083PDE9A
T17852DI0175Heart failure[ICD-11: BD10-BD1Z]O76083PDE9A
T17852DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O76083PDE9A
T17852DI0331Parkinsonism[ICD-11: 8A00]O76083PDE9A
T17852DI0370Schizophrenia[ICD-11: 6A20]O76083PDE9A
T17852DI0381Sickle-cell disorder[ICD-11: 3A51]O76083PDE9A
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T82078DI0346Prostate cancer[ICD-11: 2C82]O60603TLR2

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