Leonuriside A



Compound IDCDAMM01517
Common nameLeonuriside A
IUPAC name2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC14H20O9

Experimental data

Retention time9.82
Adduct[M+H]+
Actual mz333.122
Theoretical mz333.118
Error11.18
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5539

Identifiers and class information

Inchi keyNOQYJICHFNSIFZ-UHFFFAOYNA-N
SmilesOC=1C=C(OC)C(OC2OC(CO)C(O)C(O)C2O)=C(OC)C1
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
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)332.307
Computed dipole moment(dipole)8.063
Total solvent accessible surface area (SASA)538.853
Hydrophobic component of SASA (FOSA)281.897
Hydrophilic component of SASA (FISA)189.744
Pie component of the SASA (PISA)67.213
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)964.791
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)11.5
Free energy of solvation of dipole (dip^2/V)0.0673891
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0477213
Globularity descriptor (glob)0.876294
Predicted polarizability in cubic angstroms (QPpolrz)26.678
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.215
Predicted octanol/gas partition coefficient (QPlogPoct)22.853
Predicted water/gas partition coefficient (QPlogPw)19.208
Predicted octanol/water partition coefficient (QPlogPo/w)-0.628
Predicted aqueous solubility (QPlogS)-1.541
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.06
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.854
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)157.239
Predicted brain/blood partition coefficient (QPlogBB)-1.687
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)66.977
Predicted skin permeability, log Kp (QPlogKp)-3.82
PM3 calculated ionization potential (IP(ev))8.965
PM3 calculated electron affinity (EA(eV))-0.039
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.936
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)62.581
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)133.414
Number of nitrogen and oxygen atoms (#NandO)9
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
P11387TOP1DNA topoisomerase IT09826SEA
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction and SEA
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SEA
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SwissTargetPrediction and SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P63316TNNC1Troponin, cardiac muscleT12966SEA
P06865HEXABeta-hexosaminidase subunit alphaT63196SEA
P07686HEXBBeta-N-acetyl-D-hexosaminidase-A/BT63197SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

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
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
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
T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
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
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
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
T63196DI0242Lysosomal disease[ICD-11: 5C56]P06865HEXA
T63197DI0242Lysosomal disease[ICD-11: 5C56]P07686HEXB
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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