5\'-Hydroxy-2\'-methoxy-3,4-methylenedioxyfurano[2\'\',3\'\':4\',3\']chalcone



Compound IDCDAMM00907
Common name5\'-Hydroxy-2\'-methoxy-3,4-methylenedioxyfurano[2\'\',3\'\':4\',3\']chalcone
IUPAC name3-(1,3-benzodioxol-5-yl)-1-(7-hydroxy-4-methoxy-1-benzofuran-5-yl)prop-2-en-1-one
Molecular formulaC19H14O6

Experimental data

Retention time0.47
Adduct[M+H]+
Actual mz339.091
Theoretical mz339.086
Error13.05
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1302

Identifiers and class information

Inchi keyYNUGACKHHNAYKR-DUXPYHPUSA-N
SmilesO=C(C=CC1=CC=C2OCOC2=C1)C3=CC(O)=C4OC=CC4=C3OC
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

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)6
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)338.316
Computed dipole moment(dipole)3.172
Total solvent accessible surface area (SASA)546.109
Hydrophobic component of SASA (FOSA)166.466
Hydrophilic component of SASA (FISA)90.183
Pie component of the SASA (PISA)289.46
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)971.709
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)5.5
Free energy of solvation of dipole (dip^2/V)0.0103518
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0100712
Globularity descriptor (glob)0.86878
Predicted polarizability in cubic angstroms (QPpolrz)31.646
Predicted hexadecane/gas partition coefficient (QPlogPC16)10.205
Predicted octanol/gas partition coefficient (QPlogPoct)14.734
Predicted water/gas partition coefficient (QPlogPw)9.174
Predicted octanol/water partition coefficient (QPlogPo/w)2.818
Predicted aqueous solubility (QPlogS)-3.314
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.914
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.036
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1382.6
Predicted brain/blood partition coefficient (QPlogBB)-0.595
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)702.142
Predicted skin permeability, log Kp (QPlogKp)-1.586
PM3 calculated ionization potential (IP(ev))8.807
PM3 calculated electron affinity (EA(eV))0.944
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.035
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)83.214
Number of nitrogen and oxygen atoms (#NandO)6
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
P05067APPBeta amyloid A4 proteinT87024SEA
P23280CA6Carbonic anhydrase VIT06569SEA
P27338MAOBMonoamine oxidase BT83011SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
P17936IGFBP3Insulin-like growth factor binding protein 3T33455SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SwissTargetPrediction and SEA
Q92630DYRK2Dual-specificity tyrosine-phosphorylation regulated kinase 2T39486SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
Q7RTX1TAS1R1Taste receptorT41263SEA
Q09470KCNA1Voltage-gated potassium channel Kv1.1T85272SEA
P22459KCNA4Voltage-gated A-type potassium channelT15665SEA
P16389KCNA2Voltage-gated potassium channel Kv1.2T19492SEA
H3BPQ1TCF4Transcription factor 7-like 2T54646SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T76914DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P22001KCNA3
T76914DI0351Psoriasis[ICD-11: EA90]P22001KCNA3
T76914DI0352Psoriatic arthritis[ICD-11: FA21]P22001KCNA3
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1

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