5-Hydroxy-L-tryptophan



Compound IDCDAMM01842
Common name5-Hydroxy-L-tryptophan
IUPAC name2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Molecular formulaC11H12N2O3

Experimental data

Retention time10.73
Adduct[M+H]+
Actual mz221.09
Theoretical mz221.092
Error11.2
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8086

Identifiers and class information

Inchi keyLDCYZAJDBXYCGN-UHFFFAOYNA-N
SmilesO=C(O)C(N)CC1=CNC=2C=CC(O)=CC21
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Plant source

  • Curcuma longa 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)5
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)220.227
    Computed dipole moment(dipole)6.545
    Total solvent accessible surface area (SASA)422.902
    Hydrophobic component of SASA (FOSA)50.957
    Hydrophilic component of SASA (FISA)216.653
    Pie component of the SASA (PISA)155.291
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)703.206
    Number of hydrogen bond donors (donorHB)5
    Number of hydrogen bond acceptors (accptHB)3.75
    Free energy of solvation of dipole (dip^2/V)0.0609185
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0198279
    Globularity descriptor (glob)0.904303
    Predicted polarizability in cubic angstroms (QPpolrz)20.261
    Predicted hexadecane/gas partition coefficient (QPlogPC16)8.642
    Predicted octanol/gas partition coefficient (QPlogPoct)16.789
    Predicted water/gas partition coefficient (QPlogPw)13.181
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.766
    Predicted aqueous solubility (QPlogS)-0.873
    Conformation-independent predicted aqueous solubility (CIQPlogS)-1.406
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.74
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)5.519
    Predicted brain/blood partition coefficient (QPlogBB)-1.106
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.523
    Predicted skin permeability, log Kp (QPlogKp)-6.548
    PM3 calculated ionization potential (IP(ev))8.091
    PM3 calculated electron affinity (EA(eV))-0.031
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)-0.781
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)29.881
    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)108.459
    Number of nitrogen and oxygen atoms (#NandO)5
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)1

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P16083NQO2Quinone reductase 2T75498SEA
    P08473MMENeprilysinT05409SEA
    P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction and SEA
    P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction and SEA
    P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction and SEA
    P28222HTR1BSerotonin 1b (5-HT1b) receptorT07806SEA
    P28221HTR1DSerotonin 1d (5-HT1d) receptorT11072SEA
    P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction and SEA
    P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SEA
    P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction and SEA
    P43005SLC1A1Excitatory amino acid transporter 3T31721SEA
    P39086GRIK1Glutamate receptor ionotropic kainate 1T73495SEA
    P42261GRIA1Glutamate receptor ionotropic, AMPA 1T33584SEA
    Q16478GRIK5Glutamate receptor ionotropic kainate 5T87930SEA
    P42262GRIA2Glutamate receptor ionotropic, AMPA 2T42392SEA
    P05164MPOMyeloperoxidaseT23471SEA
    P07101THTyrosine 3-hydroxylaseT62390SEA
    Q16719KYNUKynureninaseT99912SEA
    Q8NER1TRPV1Vanilloid receptorT83193SEA
    P08235NR3C2Mineralocorticoid receptorT72168SEA
    P04150NR3C1Glucocorticoid receptorT40016SEA
    Q01650SLC7A5L-type amino acid transporter 1 (by homology)T48330SEA
    P08253MMP2Matrix metalloproteinase 2T68251SEA
    P22894MMP8Matrix metalloproteinase 8T08856SEA
    P14780MMP9Matrix metalloproteinase 9T54156SEA
    P03956MMP1Matrix metalloproteinase 1T52450SEA
    P35372OPRM1Mu opioid receptorT47768SEA
    P10827THRAThyroid hormone receptor alphaT79591SEA
    P10828THRBThyroid hormone receptor beta-1T98933SEA
    P06276BCHEButyrylcholinesteraseT99799SEA
    P35270SPRSubstance-P receptorT47094SEA
    P07711CTSLCathepsin LT98691SEA
    Q92847GHSRGhrelin receptorT59604SEA
    P41143OPRD1Delta opioid receptorT58992SEA
    P31749AKT1Serine/threonine-protein kinase AKTT67619SEA
    Q6P179ERAP2Endoplasmic reticulum aminopeptidase 2T65818SEA
    P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SEA
    P48039MTNR1AMelatonin receptor 1AT97613SEA
    P49286MTNR1BMelatonin receptor 1BT48268SEA
    P42892ECE1Endothelin-converting enzyme 1T50970SEA
    P25101EDNRAEndothelin receptor ET-AT23499SEA
    P30872SSTR1Somatostatin receptor 1T16633SEA
    P32745SSTR3Somatostatin receptor 3T13644SEA
    P32239CCKBRCholecystokinin B receptor (by homology)T05849SEA
    P50281MMP14Matrix metalloproteinase 14T65019SEA
    Q9Y243AKT3Serine/threonine-protein kinase AKTT71266SEA
    Q13976PRKG1cGMP-dependent protein kinase 1 betaT78543SEA
    P32238CCKARCholecystokinin A receptorT28330SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P14679TYRTyrosinaseT97035SEA
    Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
    P15735PHKG2Phosphorylase kinase gamma subunit 2T69208SEA
    P41240CSKTyrosine-protein kinase CSKT08741SEA
    Q13237PRKG2cGMP-dependent protein kinase 2T23606SEA
    P30939HTR1FSerotonin 1f (5-HT1f) receptorT78656SEA
    O14733MAP2K7Dual specificity mitogen-activated protein kinase kinase 7T53159SEA
    Q8IU80TMPRSS6Transmembrane protease serine 6T13863SEA
    P05129PRKCGProtein kinase C gammaT47107SEA
    Q5VT25CDC42BPASerine or threonine-protein kinase MRCK-AT00075SEA
    P51511MMP15Matrix metalloproteinase 15T81658SEA
    P28336NMBRNeuromedin B receptorT68887SEA
    P37840SNCAAlpha-synucleinT03644SEA
    P22736NR4A1Nuclear receptor subfamily 4 group A member 1T41119SEA
    P28336NMBRNeuromedin B receptorT68887SEA
    P12004PCNAProliferating cell nuclear antigenT21782SEA
    Q9UQM7CAMK2ACaM kinase II alphaT18299SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q9NQS5GPR84G-protein coupled receptor 84T98091SEA
    O43781DYRK3Dual-specificity tyrosine-phosphorylation regulated kinase 3T97149SEA
    Q06609RAD51DNA repair protein RAD51 homolog 1T63083SEA
    P42263GRIA3Glutamate receptor AMPA 3T62391SEA
    Q6ZQN7SLCO4C1Organic anion transporter M1T36053SEA
    P47870GABRB2GABA(A) receptor beta-2T80387SEA
    P35270SPRSubstance-P receptorT47094SEA
    Q9ULZ9MMP17Matrix metalloproteinase-17T55616SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
    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
    T07806DI0264Migraine[ICD-11: 8A80]P28222HTR1B
    T07806DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28222HTR1B
    T07806DI0354Psychotic disorder[ICD-11: 6A20-6A25]P28222HTR1B
    T07806DI0370Schizophrenia[ICD-11: 6A20]P28222HTR1B
    T11072DI0264Migraine[ICD-11: 8A80]P28221HTR1D
    T11072DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28221HTR1D
    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
    T84117DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28566HTR1E
    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
    T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
    T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
    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
    T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
    T72168DI0018Adrenocortical insufficiency[ICD-11: 5A74]P08235NR3C2
    T72168DI0083Chronic kidney disease[ICD-11: GB61]P08235NR3C2
    T72168DI0100Contraceptive management[ICD-11: QA21]P08235NR3C2
    T72168DI0175Heart failure[ICD-11: BD10-BD1Z]P08235NR3C2
    T72168DI0190Hypertension[ICD-11: BA00-BA04]P08235NR3C2
    T72168DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P08235NR3C2
    T40016DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P04150NR3C1
    T40016DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P04150NR3C1
    T40016DI0037Asthma[ICD-11: CA23]P04150NR3C1
    T40016DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P04150NR3C1
    T40016DI0108Cushing syndrome[ICD-11: 5A70]P04150NR3C1
    T40016DI0280Muscular dystrophy[ICD-11: 8C70]P04150NR3C1
    T40016DI0314Oesophagitis[ICD-11: DA24]P04150NR3C1
    T40016DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P04150NR3C1
    T40016DI0366Rheumatoid arthritis[ICD-11: FA20]P04150NR3C1
    T40016DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04150NR3C1
    T40016DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P04150NR3C1
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    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
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
    T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
    T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
    T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
    T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
    T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
    T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
    T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
    T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
    T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
    T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
    T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
    T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
    T79591DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10827THRA
    T79591DI0197Hypo-thyroidism[ICD-11: 5A00]P10827THRA
    T98933DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P10828THRB
    T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
    T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
    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
    T59604DI0087Chronic pain[ICD-11: MG30]Q92847GHSR
    T59604DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]Q92847GHSR
    T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
    T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
    T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
    T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
    T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
    T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
    T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
    T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
    T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
    T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
    T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
    T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
    T71266DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q9Y243AKT3
    T28330DI0210Influenza[ICD-11: 1E30-1E32]P32238CCKAR
    T28330DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P32238CCKAR
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T78656DI0264Migraine[ICD-11: 8A80]P30939HTR1F
    T78656DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30939HTR1F
    T47107DI0012Acute myeloid leukaemia[ICD-11: 2A60]P05129PRKCG
    T47107DI0248Mastocytosis[ICD-11: 2A21]P05129PRKCG
    T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
    T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
    T03644DI0025Alzheimer disease[ICD-11: 8A20]P37840SNCA
    T03644DI0044Autonomic nervous system disorder[ICD-11: 8D87]P37840SNCA
    T03644DI0331Parkinsonism[ICD-11: 8A00]P37840SNCA
    T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
    T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
    T21782DI0308Obesity[ICD-11: 5B80-5B81]P12004PCNA
    T18299DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UQM7CAMK2A
    T98091DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q9NQS5GPR84
    T98091DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NQS5GPR84
    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
    T80387DI0117Depression[ICD-11: 6A70-6A7Z]P47870GABRB2
    T80387DI0214Insomnia[ICD-11: 7A00-7A0Z]P47870GABRB2
    T80387DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P47870GABRB2
    T80387DI0411Tonus and reflex abnormality[ICD-11: MB47]P47870GABRB2
    T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
    T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR

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