Medicarpin 3-O-(6\'-malonylglucoside)



Compound IDCDAMM02673
Common nameMedicarpin 3-O-(6\'-malonylglucoside)
IUPAC name3-oxo-3-[[3,4,5-trihydroxy-6-[(9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-yl)oxy]oxan-2-yl]methoxy]propanoic acid
Molecular formulaC25H26O12

Experimental data

Retention time11.77
Adduct[M+H]+
Actual mz519.144
Theoretical mz519.149
Error10.55
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.8451

Identifiers and class information

Inchi keyBQAJKXKYTQTBDK-UHFFFAOYNA-N
SmilesO=C(O)CC(=O)OCC1OC(OC2=CC=C3C(OCC4C5=CC=C(OC)C=C5OC34)=C2)C(O)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)10
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)518.473
Computed dipole moment(dipole)3.709
Total solvent accessible surface area (SASA)735.734
Hydrophobic component of SASA (FOSA)304.684
Hydrophilic component of SASA (FISA)231.862
Pie component of the SASA (PISA)199.188
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1406.52
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)12.8
Free energy of solvation of dipole (dip^2/V)0.0097817
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0301335
Globularity descriptor (glob)0.825167
Predicted polarizability in cubic angstroms (QPpolrz)45.616
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.963
Predicted octanol/gas partition coefficient (QPlogPoct)26.886
Predicted water/gas partition coefficient (QPlogPw)19.217
Predicted octanol/water partition coefficient (QPlogPo/w)1.819
Predicted aqueous solubility (QPlogS)-3.637
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.438
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.503
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)15.876
Predicted brain/blood partition coefficient (QPlogBB)-2.309
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.145
Predicted skin permeability, log Kp (QPlogKp)-4.131
PM3 calculated ionization potential (IP(ev))8.889
PM3 calculated electron affinity (EA(eV))-0.057
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.556
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)33.17
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)184.443
Number of nitrogen and oxygen atoms (#NandO)12
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
O14842FFAR1Free fatty acid receptor 1T25608SEA
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P48039MTNR1AMelatonin receptor 1AT97613SEA
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
P60842EIF4A1Eukaryotic initiation factor 4A-IT86805SwissTargetPrediction
P09382LGALS1Galectin-1T09544SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

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
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T25608DI0417Type 2 diabetes mellitus[ICD-11: 5A11]O14842FFAR1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T97613DI0214Insomnia[ICD-11: 7A00-7A0Z]P48039MTNR1A
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
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
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T86805DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P60842EIF4A1
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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