2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-4-(prop-2-en-1-yl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-7-one



Compound IDCDAMM00133
Common name2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-4-(prop-2-en-1-yl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-7-one
IUPAC name2-(1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-4-prop-2-enyl-2,3,3a,4-tetrahydro-1-benzofuran-7-one
Molecular formulaC19H20O5

Experimental data

Retention time36.38
Adduct[M+H]+
Actual mz329.139
Theoretical mz329.138
Error2.3
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.2198

Identifiers and class information

Inchi keyGNVSNCNUCPCVCC-MKJYOJNNNA-N
SmilesCC1C2C(C=CC(=O)C2(OC1C3=CC4=C(C=C3)OCO4)O)CC=C
SuperclassOrganoheterocyclic compounds
ClassBenzodioxoles

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)3
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)328.364
Computed dipole moment(dipole)8.413
Total solvent accessible surface area (SASA)539.545
Hydrophobic component of SASA (FOSA)246.428
Hydrophilic component of SASA (FISA)75.684
Pie component of the SASA (PISA)217.432
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)984.169
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)5
Free energy of solvation of dipole (dip^2/V)0.0719088
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0092671
Globularity descriptor (glob)0.886851
Predicted polarizability in cubic angstroms (QPpolrz)33.383
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.791
Predicted octanol/gas partition coefficient (QPlogPoct)15.887
Predicted water/gas partition coefficient (QPlogPw)8.739
Predicted octanol/water partition coefficient (QPlogPo/w)3.123
Predicted aqueous solubility (QPlogS)-3.86
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.585
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.4
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1897.51
Predicted brain/blood partition coefficient (QPlogBB)-0.259
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)988.63
Predicted skin permeability, log Kp (QPlogKp)-1.86
PM3 calculated ionization potential (IP(ev))8.985
PM3 calculated electron affinity (EA(eV))0.465
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)0.227
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)71.244
Number of nitrogen and oxygen atoms (#NandO)5
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
P25101EDNRAEndothelin receptor ET-AT23499SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
Q92630DYRK2Dual-specificity tyrosine-phosphorylation regulated kinase 2T39486SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB

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