4-(3-methylbut-2-enyl)-L-tryptophan



Compound IDCDAMM00325
Common name4-(3-methylbut-2-enyl)-L-tryptophan
IUPAC name(2S)-2-amino-3-[4-(3-methylbut-2-enyl)-1H-indol-3-yl]propanoic acid
Molecular formulaC16H20N2O2

Experimental data

Retention time13.54
Adduct[M+H]+
Actual mz273.156
Theoretical mz273.16
Error11.91
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.5

Identifiers and class information

Inchi keyMZSPRSJAOSKAAT-ZDUSSCGKSA-N
SmilesO=C(O)C(N)CC1=CNC2=CC=CC(=C21)CC=C(C)C
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Plant source

  • Pedalium murex L.

    • 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)272.346
    Computed dipole moment(dipole)5.144
    Total solvent accessible surface area (SASA)545.405
    Hydrophobic component of SASA (FOSA)209.873
    Hydrophilic component of SASA (FISA)171.526
    Pie component of the SASA (PISA)164.006
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)938.021
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)3
    Free energy of solvation of dipole (dip^2/V)0.0282055
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.011001
    Globularity descriptor (glob)0.849678
    Predicted polarizability in cubic angstroms (QPpolrz)29.099
    Predicted hexadecane/gas partition coefficient (QPlogPC16)10.174
    Predicted octanol/gas partition coefficient (QPlogPoct)17.231
    Predicted water/gas partition coefficient (QPlogPw)10.804
    Predicted octanol/water partition coefficient (QPlogPo/w)0.362
    Predicted aqueous solubility (QPlogS)-2.943
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.673
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.665
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)14.785
    Predicted brain/blood partition coefficient (QPlogBB)-0.984
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.319
    Predicted skin permeability, log Kp (QPlogKp)-5.59
    PM3 calculated ionization potential (IP(ev))8.154
    PM3 calculated electron affinity (EA(eV))-0.044
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.14
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)50.001
    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)86.458
    Number of nitrogen and oxygen atoms (#NandO)4
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)2

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P30531SLC6A1GABA transporter 1T62184SwissTargetPrediction
    P54289CACNA2D1Voltage-gated calcium channel alpha2/delta subunit 1 (by homology)T84316SwissTargetPrediction
    P43004SLC1A2Excitatory amino acid transporter 2T95438SwissTargetPrediction
    P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
    P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction
    P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
    P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
    P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction
    Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
    P43005SLC1A1Excitatory amino acid transporter 3T31721SwissTargetPrediction
    P39086GRIK1Glutamate receptor ionotropic kainate 1T73495SwissTargetPrediction and SEA
    Q13002GRIK2Glutamate receptor ionotropic kainate 2T58178SEA
    P42261GRIA1Glutamate receptor ionotropic, AMPA 1T33584SEA
    P42262GRIA2Glutamate receptor ionotropic, AMPA 2T42392SwissTargetPrediction
    Q9H4A4RNPEPAminopeptidase BT57818SEA
    P07101THTyrosine 3-hydroxylaseT62390SEA
    Q16719KYNUKynureninaseT99912SEA
    Q01650SLC7A5L-type amino acid transporter 1 (by homology)T48330SwissTargetPrediction and SEA
    P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
    P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
    P49137MAPKAPK2MAP kinase-activated protein kinase 2T21307SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SEA
    P23975SLC6A2Norepinephrine transporterT21945SwissTargetPrediction
    P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
    P35270SPRSubstance-P receptorT47094SEA
    P07711CTSLCathepsin LT98691SEA
    P07858CTSBCathepsin (B and K)T61746SEA
    Q92847GHSRGhrelin receptorT59604SEA
    Q9UHL4DPP7Dipeptidyl peptidase IIT50773SwissTargetPrediction
    Q6P179ERAP2Endoplasmic reticulum aminopeptidase 2T65818SEA
    P50579METAP2Methionine aminopeptidase 2T75596SwissTargetPrediction
    Q9ULA0DNPEPAspartyl aminopeptidaseT45287SEA
    P42892ECE1Endothelin-converting enzyme 1T50970SEA
    P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
    P25101EDNRAEndothelin receptor ET-AT23499SEA
    P32239CCKBRCholecystokinin B receptor (by homology)T05849SEA
    P48067SLC6A9Glycine transporter 1T69685SwissTargetPrediction
    P14679TYRTyrosinaseT97035SEA
    P43003SLC1A3Excitatory amino acid transporter 1T86582SwissTargetPrediction
    P30307CDC25CDual specificity phosphatase Cdc25CT40569SEA
    Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
    P28336NMBRNeuromedin B receptorT68887SEA
    P28336NMBRNeuromedin B receptorT68887SEA
    P12004PCNAProliferating cell nuclear antigenT21782SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q8IWU9TPH2Tryptophan hydroxylaseT51593SEA
    Q9BWQ3ASCT2Alanine/serine/cysteine transporter 2T59493SEA
    Q06609RAD51DNA repair protein RAD51 homolog 1T63083SEA
    P42263GRIA3Glutamate receptor AMPA 3T62391SEA
    Q6ZQN7SLCO4C1Organic anion transporter M1T36053SEA
    O95622ADCY5Adenylate cyclase type 5T19531SEA
    P35270SPRSubstance-P receptorT47094SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T62184DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P30531SLC6A1
    T62184DI0274Multiple myeloma[ICD-11: 2A83]P30531SLC6A1
    T84316DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P54289CACNA2D1
    T84316DI0190Hypertension[ICD-11: BA00-BA04]P54289CACNA2D1
    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
    T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
    T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
    T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
    T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
    T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
    T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
    T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
    T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
    T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
    T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
    T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
    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
    T55959DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q01959SLC6A3
    T55959DI0051Bipolar disorder[ICD-11: 6A60]Q01959SLC6A3
    T55959DI0101Corneal disease[ICD-11: 9A76-9A78]Q01959SLC6A3
    T55959DI0290Narcolepsy[ICD-11: 7A20]Q01959SLC6A3
    T55959DI0308Obesity[ICD-11: 5B80-5B81]Q01959SLC6A3
    T55959DI0331Parkinsonism[ICD-11: 8A00]Q01959SLC6A3
    T73495DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P39086GRIK1
    T73495DI0396Substance abuse[ICD-11: 6C40]P39086GRIK1
    T33584DI0298Neuropathy[ICD-11: 8C0Z]P42261GRIA1
    T42392DI0298Neuropathy[ICD-11: 8C0Z]P42262GRIA2
    T62390DI0019Adrenomedullary hyperfunction[ICD-11: 5A75]P07101TH
    T62390DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P07101TH
    T99912DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q16719KYNU
    T99912DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q16719KYNU
    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
    T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
    T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
    T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
    T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
    T21945DI0013Acute pain[ICD-11: MG31]P23975SLC6A2
    T21945DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P23975SLC6A2
    T21945DI0087Chronic pain[ICD-11: MG30]P23975SLC6A2
    T21945DI0101Corneal disease[ICD-11: 9A76-9A78]P23975SLC6A2
    T21945DI0117Depression[ICD-11: 6A70-6A7Z]P23975SLC6A2
    T21945DI0166Glaucoma[ICD-11: 9C61]P23975SLC6A2
    T21945DI0264Migraine[ICD-11: 8A80]P23975SLC6A2
    T21945DI0301Nicotine use disorder[ICD-11: 6C4A]P23975SLC6A2
    T21945DI0308Obesity[ICD-11: 5B80-5B81]P23975SLC6A2
    T21945DI0324Pain[ICD-11: MG30-MG3Z]P23975SLC6A2
    T21945DI0395Stomach cancer[ICD-11: 2B72]P23975SLC6A2
    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
    T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
    T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
    T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
    T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
    T61746DI0023Alopecia[ICD-11: ED70]P07858CTSB
    T61746DI0025Alzheimer disease[ICD-11: 8A20]P07858CTSB
    T61746DI0037Asthma[ICD-11: CA23]P07858CTSB
    T61746DI0055Bone cancer[ICD-11: 2B5Z]P07858CTSB
    T61746DI0060Brain cancer[ICD-11: 2A00]P07858CTSB
    T61746DI0067Cardiac arrest[ICD-11: MC82]P07858CTSB
    T61746DI0074Cerebral ischaemic stroke[ICD-11: 8B11]P07858CTSB
    T61746DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07858CTSB
    T61746DI0087Chronic pain[ICD-11: MG30]P07858CTSB
    T61746DI0110Cystic fibrosis[ICD-11: CA25]P07858CTSB
    T61746DI0124Digestive system disease[ICD-11: DE2Z]P07858CTSB
    T61746DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P07858CTSB
    T61746DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P07858CTSB
    T61746DI0253Meningioma[ICD-11: 2A01]P07858CTSB
    T61746DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P07858CTSB
    T61746DI0275Multiple sclerosis[ICD-11: 8A40]P07858CTSB
    T61746DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]P07858CTSB
    T61746DI0320Osteoarthritis[ICD-11: FA00-FA05]P07858CTSB
    T61746DI0351Psoriasis[ICD-11: EA90]P07858CTSB
    T61746DI0366Rheumatoid arthritis[ICD-11: FA20]P07858CTSB
    T59604DI0087Chronic pain[ICD-11: MG30]Q92847GHSR
    T59604DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]Q92847GHSR
    T75596DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50579METAP2
    T45287DI0190Hypertension[ICD-11: BA00-BA04]Q9ULA0DNPEP
    T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
    T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
    T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
    T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
    T69685DI0370Schizophrenia[ICD-11: 6A20]P48067SLC6A9
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
    T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
    T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
    T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
    T21782DI0308Obesity[ICD-11: 5B80-5B81]P12004PCNA
    T51593DI0066Carcinoid syndrome[ICD-11: 5B10]Q8IWU9TPH2
    T51593DI0389Small intestine developmental anomaly[ICD-11: DA90]Q8IWU9TPH2
    T63083DI0048B-cell lymphoma[ICD-11: 2A86]Q06609RAD51
    T63083DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q06609RAD51
    T62391DI0298Neuropathy[ICD-11: 8C0Z]P42263GRIA3
    T36053DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q6ZQN7SLCO4C1
    T36053DI0175Heart failure[ICD-11: BD10-BD1Z]Q6ZQN7SLCO4C1
    T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
    T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR

    Copyright © 2025