2-({6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol



Compound IDCDAMM00185
Common name2-({6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
IUPAC name2-[[6-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC23H29NO8

Experimental data

Retention time18.5
Adduct[M+H]+
Actual mz448.196
Theoretical mz448.197
Error1.53
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1881

Identifiers and class information

Inchi keyHWKIERCNYOLMLM-RPIOSVOPNA-N
SmilesCN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O
SuperclassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)11
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)447.484
Computed dipole moment(dipole)2.631
Total solvent accessible surface area (SASA)663.505
Hydrophobic component of SASA (FOSA)274.588
Hydrophilic component of SASA (FISA)236.756
Pie component of the SASA (PISA)152.162
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1317.55
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)12.75
Free energy of solvation of dipole (dip^2/V)0.0052543
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0470697
Globularity descriptor (glob)0.87599
Predicted polarizability in cubic angstroms (QPpolrz)40.964
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.533
Predicted octanol/gas partition coefficient (QPlogPoct)29.612
Predicted water/gas partition coefficient (QPlogPw)22.881
Predicted octanol/water partition coefficient (QPlogPo/w)-0.017
Predicted aqueous solubility (QPlogS)-1.4
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.891
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.99
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)14.049
Predicted brain/blood partition coefficient (QPlogBB)-1.758
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)5.446
Predicted skin permeability, log Kp (QPlogKp)-6.353
PM3 calculated ionization potential (IP(ev))8.677
PM3 calculated electron affinity (EA(eV))-0.206
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-0.502
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)34.427
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)149.116
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P14416DRD2Dopamine D2 receptorT67162SEA
Q92731ESR2Estrogen receptor betaT80896SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P21728DRD1Dopamine D1 receptorT22118SEA
P21918DRD5Dopamine D5 receptorT46828SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
O43613HCRTR1Orexin receptor 1T73482SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P63316TNNC1Troponin, cardiac muscleT12966SEA
Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
Q9UGI6KCNN3Small conductance calcium-activated potassium channel protein 3T04388SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T67162DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P14416DRD2
T67162DI0025Alzheimer disease[ICD-11: 8A20]P14416DRD2
T67162DI0037Asthma[ICD-11: CA23]P14416DRD2
T67162DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P14416DRD2
T67162DI0051Bipolar disorder[ICD-11: 6A60]P14416DRD2
T67162DI0063Breathing abnormality[ICD-11: MD11]P14416DRD2
T67162DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P14416DRD2
T67162DI0073Cerebral ischaemia[ICD-11: 8B1Z]P14416DRD2
T67162DI0117Depression[ICD-11: 6A70-6A7Z]P14416DRD2
T67162DI0124Digestive system disease[ICD-11: DE2Z]P14416DRD2
T67162DI0137Essential hypertension[ICD-11: BA00]P14416DRD2
T67162DI0142Faecal incontinence[ICD-11: ME07]P14416DRD2
T67162DI0156Gangrene[ICD-11: MC85]P14416DRD2
T67162DI0166Glaucoma[ICD-11: 9C61]P14416DRD2
T67162DI0175Heart failure[ICD-11: BD10-BD1Z]P14416DRD2
T67162DI0185Hyperaemia[ICD-11: 9A61-9B7Y]P14416DRD2
T67162DI0190Hypertension[ICD-11: BA00-BA04]P14416DRD2
T67162DI0196Hypotension[ICD-11: BA20-BA21]P14416DRD2
T67162DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]P14416DRD2
T67162DI0214Insomnia[ICD-11: 7A00-7A0Z]P14416DRD2
T67162DI0222Itching[ICD-11: 1F28-1G07]P14416DRD2
T67162DI0264Migraine[ICD-11: 8A80]P14416DRD2
T67162DI0293Nausea/vomiting[ICD-11: MD90]P14416DRD2
T67162DI0324Pain[ICD-11: MG30-MG3Z]P14416DRD2
T67162DI0331Parkinsonism[ICD-11: 8A00]P14416DRD2
T67162DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P14416DRD2
T67162DI0340Postpartum haemorrhage[ICD-11: JA43]P14416DRD2
T67162DI0354Psychotic disorder[ICD-11: 6A20-6A25]P14416DRD2
T67162DI0356Pulmonary hypertension[ICD-11: BB01]P14416DRD2
T67162DI0370Schizophrenia[ICD-11: 6A20]P14416DRD2
T67162DI0396Substance abuse[ICD-11: 6C40]P14416DRD2
T67162DI0408Thyrotoxicosis[ICD-11: 5A02]P14416DRD2
T67162DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14416DRD2
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T22118DI0003Abortion[ICD-11: JA00]P21728DRD1
T22118DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21728DRD1
T22118DI0190Hypertension[ICD-11: BA00-BA04]P21728DRD1
T22118DI0331Parkinsonism[ICD-11: 8A00]P21728DRD1
T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
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
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
T73482DI0117Depression[ICD-11: 6A70-6A7Z]O43613HCRTR1
T73482DI0214Insomnia[ICD-11: 7A00-7A0Z]O43613HCRTR1
T73482DI0317Opioid use disorder[ICD-11: 6C43]O43613HCRTR1
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
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T11911DI0285Myelopathy[ICD-11: 8B42]Q92952KCNN1
T04388DI0285Myelopathy[ICD-11: 8B42]Q9UGI6KCNN3
T86271DI0285Myelopathy[ICD-11: 8B42]Q9H2S1KCNN2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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