Bufotenine O-glucoside



Compound IDCDAMM02446
Common nameBufotenine O-glucoside
IUPAC name2-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC18H26N2O6

Experimental data

Retention time4.86
Adduct[2M+H]+
Actual mz733.364
Theoretical mz733.365
Error1.19
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1562

Identifiers and class information

Inchi keyGNUFCIHWKPAEBF-UHFFFAOYNA-N
SmilesOCC1OC(OC=2C=CC=3NC=C(C3C2)CCN(C)C)C(O)C(O)C1O
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)366.413
Computed dipole moment(dipole)2.833
Total solvent accessible surface area (SASA)604.578
Hydrophobic component of SASA (FOSA)293.939
Hydrophilic component of SASA (FISA)172.191
Pie component of the SASA (PISA)138.448
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1123.76
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)11.25
Free energy of solvation of dipole (dip^2/V)0.0071414
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0416088
Globularity descriptor (glob)0.864626
Predicted polarizability in cubic angstroms (QPpolrz)33.72
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.029
Predicted octanol/gas partition coefficient (QPlogPoct)24.402
Predicted water/gas partition coefficient (QPlogPw)19.485
Predicted octanol/water partition coefficient (QPlogPo/w)-0.063
Predicted aqueous solubility (QPlogS)-1.087
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.818
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.109
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)57.532
Predicted brain/blood partition coefficient (QPlogBB)-1.176
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)24.994
Predicted skin permeability, log Kp (QPlogKp)-5.308
PM3 calculated ionization potential (IP(ev))8.053
PM3 calculated electron affinity (EA(eV))-0.097
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.673
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)58.078
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)117.643
Number of nitrogen and oxygen atoms (#NandO)8
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
O00754MAN2B1Lysosomal alpha-mannosidaseT63156SwissTargetPrediction
Q16739UGCGCeramide glucosyltransferaseT14908SwissTargetPrediction
O43451MGAMMaltase-glucoamylaseT92777SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P55210CASP7Caspase-7T72252SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SEA
P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SEA
P31645SLC6A4Serotonin transporter (by homology)T27812SEA
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SEA
P28222HTR1BSerotonin 1b (5-HT1b) receptorT07806SwissTargetPrediction and SEA
P28221HTR1DSerotonin 1d (5-HT1d) receptorT11072SwissTargetPrediction and SEA
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction and SEA
P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SEA
P50406HTR6Serotonin 6 (5-HT6) receptorT16691SEA
P05164MPOMyeloperoxidaseT23471SEA
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SEA
P48039MTNR1AMelatonin receptor 1AT97613SwissTargetPrediction and SEA
P49286MTNR1BMelatonin receptor 1BT48268SwissTargetPrediction and SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P31391SSTR4Somatostatin receptor 4T62974SEA
P30872SSTR1Somatostatin receptor 1T16633SEA
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
P37840SNCAAlpha-synucleinT03644SEA
P22736NR4A1Nuclear receptor subfamily 4 group A member 1T41119SwissTargetPrediction
P01111NRASGTPase NRasT35486SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P17707AMD1S-adenosylmethionine decarboxylase 1T55922SwissTargetPrediction
P16444DPEP1Renal dipeptidaseT41201SwissTargetPrediction
P35270SPRSubstance-P receptorT47094SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T63156DI0242Lysosomal disease[ICD-11: 5C56]O00754MAN2B1
T14908DI0242Lysosomal disease[ICD-11: 5C56]Q16739UGCG
T14908DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]Q16739UGCG
T92777DI0009Acute diabete complication[ICD-11: 5A2Y]O43451MGAM
T92777DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]O43451MGAM
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
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
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
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
T16691DI0025Alzheimer disease[ICD-11: 8A20]P50406HTR6
T16691DI0370Schizophrenia[ICD-11: 6A20]P50406HTR6
T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T03644DI0025Alzheimer disease[ICD-11: 8A20]P37840SNCA
T03644DI0044Autonomic nervous system disorder[ICD-11: 8D87]P37840SNCA
T03644DI0331Parkinsonism[ICD-11: 8A00]P37840SNCA
T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
T55922DI0004Acidosis[ICD-11: 5C73]P17707AMD1
T41201DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P16444DPEP1
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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