Isolimocitrol 3-glucoside



Compound IDCDAMM02751
Common nameIsolimocitrol 3-glucoside
IUPAC name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Molecular formulaC24H26O14

Experimental data

Retention time26.93
Adduct[M+H]+
Actual mz539.143
Theoretical mz539.139
Error6.54
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9171

Identifiers and class information

Inchi keyAMJOONKCBORCKA-UHFFFAOYNA-N
SmilesO=C1C(OC2OC(CO)C(O)C(O)C2O)=C(OC=3C(OC)=C(O)C(OC)=C(O)C13)C=4C=CC(OC)=C(O)C4
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)13
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)538.461
Computed dipole moment(dipole)9.649
Total solvent accessible surface area (SASA)699.543
Hydrophobic component of SASA (FOSA)349.008
Hydrophilic component of SASA (FISA)263.797
Pie component of the SASA (PISA)86.738
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1380.72
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)15.25
Free energy of solvation of dipole (dip^2/V)0.0674302
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0533987
Globularity descriptor (glob)0.85721
Predicted polarizability in cubic angstroms (QPpolrz)41.583
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.801
Predicted octanol/gas partition coefficient (QPlogPoct)31.949
Predicted water/gas partition coefficient (QPlogPw)24.728
Predicted octanol/water partition coefficient (QPlogPo/w)-0.279
Predicted aqueous solubility (QPlogS)-2.3
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.895
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.256
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)31.211
Predicted brain/blood partition coefficient (QPlogBB)-2.613
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)11.665
Predicted skin permeability, log Kp (QPlogKp)-4.828
PM3 calculated ionization potential (IP(ev))8.833
PM3 calculated electron affinity (EA(eV))0.767
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-0.798
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)13.184
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)214.03
Number of nitrogen and oxygen atoms (#NandO)14
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction and SEA
P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction and SEA
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction and SEA
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P05121SERPINE1Plasminogen activator inhibitor-1T15556SwissTargetPrediction
P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
P55072VCPTransitional endoplasmic reticulum ATPaseT12646SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P14679TYRTyrosinaseT97035SEA
P51812RPS6KA3Ribosomal protein S6 kinase alpha 3T03279SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction and SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SwissTargetPrediction and SEA
P47989XDHXanthine dehydrogenaseT40954SwissTargetPrediction and SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P63316TNNC1Troponin, cardiac muscleT12966SwissTargetPrediction
P04637TP53Tumour suppressor p53/oncoprotein Mdm2T15739SwissTargetPrediction
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
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
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T12646DI0012Acute myeloid leukaemia[ICD-11: 2A60]P55072VCP
T12646DI0274Multiple myeloma[ICD-11: 2A83]P55072VCP
T12646DI0284Myelodysplastic syndrome[ICD-11: 2A37]P55072VCP
T12646DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P55072VCP
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
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
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
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
T03279DI0249Mature B-cell leukaemia[ICD-11: 2A82]P51812RPS6KA3
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T15739DI0233Lip/oral cavity/pharynx neoplasm[ICD-11: 2B6E]P04637TP53
T15739DI0323Ovarian dysfunction[ICD-11: 5A80]P04637TP53
T15739DI0413Transplant rejection[ICD-11: NE84]P04637TP53
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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