S-Prenyl-L-cysteine



Compound IDCDAMM02162
Common nameS-Prenyl-L-cysteine
IUPAC name2-amino-3-(3-methylbut-2-enylsulfanyl)propanoic acid
Molecular formulaC8H15NO2S

Experimental data

Retention time12.71
Adduct[M+Na]+
Actual mz212.072
Theoretical mz212.071
Error4.63
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.4792

Identifiers and class information

Inchi keyULHWZNASVJIOEM-UHFFFAOYNA-N
SmilesO=C(O)C(N)CSCC=C(C)C
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)1
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)6
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)189.272
Computed dipole moment(dipole)7.781
Total solvent accessible surface area (SASA)447.876
Hydrophobic component of SASA (FOSA)255.445
Hydrophilic component of SASA (FISA)150.159
Pie component of the SASA (PISA)13.481
Weakly polar component of the SASA (WPSA)28.791
Total solvent accesible volume (volume)715.896
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)3.5
Free energy of solvation of dipole (dip^2/V)0.08457
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0135354
Globularity descriptor (glob)0.864121
Predicted polarizability in cubic angstroms (QPpolrz)18.772
Predicted hexadecane/gas partition coefficient (QPlogPC16)6.75
Predicted octanol/gas partition coefficient (QPlogPoct)13.002
Predicted water/gas partition coefficient (QPlogPw)8.438
Predicted octanol/water partition coefficient (QPlogPo/w)-0.837
Predicted aqueous solubility (QPlogS)-1.614
Conformation-independent predicted aqueous solubility (CIQPlogS)-0.589
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.714
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)23.574
Predicted brain/blood partition coefficient (QPlogBB)-0.67
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)17.425
Predicted skin permeability, log Kp (QPlogKp)-5.726
PM3 calculated ionization potential (IP(ev))9.276
PM3 calculated electron affinity (EA(eV))0.476
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.623
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)46.608
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)74.344
Number of nitrogen and oxygen atoms (#NandO)3
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
P29475NOS1Nitric-oxide synthase, brainT16117SwissTargetPrediction
P35228NOS2Nitric oxide synthase, inducibleT02703SEA
P29474NOS3Nitric-oxide synthase, endothelialT06046SEA
P15144ANPEPAminopeptidase NT67272SwissTargetPrediction
O75899GABBR2GABA-B receptorT42446SwissTargetPrediction
P09960LTA4HLeukotriene A4 hydrolaseT03691SwissTargetPrediction
P54289CACNA2D1Voltage-gated calcium channel alpha2/delta subunit 1 (by homology)T84316SwissTargetPrediction
O00222GRM8Metabotropic glutamate receptor 8T77548SEA
Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
P08473MMENeprilysinT05409SwissTargetPrediction
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction
P43005SLC1A1Excitatory amino acid transporter 3T31721SEA
P39086GRIK1Glutamate receptor ionotropic kainate 1T73495SEA
Q13002GRIK2Glutamate receptor ionotropic kainate 2T58178SEA
O15303GRM6Metabotropic glutamate receptor 6T55956SEA
P42261GRIA1Glutamate receptor ionotropic, AMPA 1T33584SwissTargetPrediction
Q16478GRIK5Glutamate receptor ionotropic kainate 5T87930SEA
Q13003GRIK3Glutamate receptor ionotropic kainate 3T68876SEA
P42262GRIA2Glutamate receptor ionotropic, AMPA 2T42392SwissTargetPrediction
O75164KDM4ALysine-specific demethylase 4AT18904SwissTargetPrediction
Q16719KYNUKynureninaseT99912SwissTargetPrediction and SEA
Q07075ENPEPAminopeptidase AT31956SwissTargetPrediction
Q01650SLC7A5L-type amino acid transporter 1 (by homology)T48330SwissTargetPrediction and SEA
P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
P49137MAPKAPK2MAP kinase-activated protein kinase 2T21307SwissTargetPrediction
P15086CPB1Carboxypeptidase BT36725SwissTargetPrediction
P52732KIF11Kinesin-like protein 1T28484SEA
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
P41229KDM5CLysine-specific demethylase 5CT85540SwissTargetPrediction
P14384CPMCarboxypeptidase MT65483SEA
Q9UGL1KDM5BLysine-specific demethylase 5BT56871SwissTargetPrediction
P46059SLC15A1Oligopeptide transporter small intestine isoformT91180SwissTargetPrediction
O60603TLR2Toll-like receptor 2T82078SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16117DI0173Headache[ICD-11: 8A80-8A84]P29475NOS1
T16117DI0264Migraine[ICD-11: 8A80]P29475NOS1
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T06046DI0287Myocardial infarction[ICD-11: BA41-BA43]P29474NOS3
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
T03691DI0012Acute myeloid leukaemia[ICD-11: 2A60]P09960LTA4H
T84316DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P54289CACNA2D1
T84316DI0190Hypertension[ICD-11: BA00-BA04]P54289CACNA2D1
T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T32060DI0009Acute diabete complication[ICD-11: 5A2Y]P28223HTR2A
T32060DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P28223HTR2A
T32060DI0073Cerebral ischaemia[ICD-11: 8B1Z]P28223HTR2A
T32060DI0270Mood disorder[ICD-11: 6A60-6E23]P28223HTR2A
T32060DI0331Parkinsonism[ICD-11: 8A00]P28223HTR2A
T32060DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28223HTR2A
T32060DI0370Schizophrenia[ICD-11: 6A20]P28223HTR2A
T83813DI0117Depression[ICD-11: 6A70-6A7Z]P28335HTR2C
T83813DI0264Migraine[ICD-11: 8A80]P28335HTR2C
T83813DI0308Obesity[ICD-11: 5B80-5B81]P28335HTR2C
T83813DI0324Pain[ICD-11: MG30-MG3Z]P28335HTR2C
T83813DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28335HTR2C
T31204DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P41595HTR2B
T31204DI0117Depression[ICD-11: 6A70-6A7Z]P41595HTR2B
T31204DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P41595HTR2B
T31204DI0354Psychotic disorder[ICD-11: 6A20-6A25]P41595HTR2B
T78709DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P08908HTR1A
T78709DI0117Depression[ICD-11: 6A70-6A7Z]P08908HTR1A
T78709DI0190Hypertension[ICD-11: BA00-BA04]P08908HTR1A
T78709DI0264Migraine[ICD-11: 8A80]P08908HTR1A
T78709DI0270Mood disorder[ICD-11: 6A60-6E23]P08908HTR1A
T79062DI0025Alzheimer disease[ICD-11: 8A20]P34969HTR7
T79062DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34969HTR7
T79062DI0051Bipolar disorder[ICD-11: 6A60]P34969HTR7
T79062DI0117Depression[ICD-11: 6A70-6A7Z]P34969HTR7
T79062DI0265Mild neurocognitive disorder[ICD-11: 6D71]P34969HTR7
T79062DI0331Parkinsonism[ICD-11: 8A00]P34969HTR7
T79062DI0370Schizophrenia[ICD-11: 6A20]P34969HTR7
T73495DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P39086GRIK1
T73495DI0396Substance abuse[ICD-11: 6C40]P39086GRIK1
T33584DI0298Neuropathy[ICD-11: 8C0Z]P42261GRIA1
T42392DI0298Neuropathy[ICD-11: 8C0Z]P42262GRIA2
T99912DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q16719KYNU
T99912DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q16719KYNU
T31956DI0190Hypertension[ICD-11: BA00-BA04]Q07075ENPEP
T89697DI0117Depression[ICD-11: 6A70-6A7Z]P14902IDO1
T21307DI0011Acute laryngitis/tracheitis[ICD-11: CA05]P49137MAPKAPK2
T21307DI0181Hidradenitis suppurativa[ICD-11: ED92]P49137MAPKAPK2
T21307DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P49137MAPKAPK2
T21307DI0334Peritoneal cancer[ICD-11: 2C51]P49137MAPKAPK2
T21307DI0352Psoriatic arthritis[ICD-11: FA21]P49137MAPKAPK2
T21307DI0366Rheumatoid arthritis[ICD-11: FA20]P49137MAPKAPK2
T21307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49137MAPKAPK2
T28484DI0012Acute myeloid leukaemia[ICD-11: 2A60]P52732KIF11
T28484DI0172Head and neck cancer[ICD-11: 2D42]P52732KIF11
T28484DI0241Lymphoma[ICD-11: 2A80-2A86]P52732KIF11
T28484DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P52732KIF11
T28484DI0274Multiple myeloma[ICD-11: 2A83]P52732KIF11
T28484DI0321Ovarian cancer[ICD-11: 2C73]P52732KIF11
T28484DI0361Renal cell carcinoma[ICD-11: 2C90]P52732KIF11
T28484DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P52732KIF11
T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
T82078DI0346Prostate cancer[ICD-11: 2C82]O60603TLR2

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