3\'-Prenylrubranine



Compound IDCDAMM02761
Common name3\'-Prenylrubranine
IUPAC name1-[9-hydroxy-1,5,5-trimethyl-10-(3-methylbut-2-enyl)-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7,9,11-trien-8-yl]-3-phenylprop-2-en-1-one
Molecular formulaC30H34O4

Experimental data

Retention time12.89
Adduct[M+H]+
Actual mz459.254
Theoretical mz459.253
Error1.58
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2337

Identifiers and class information

Inchi keyFYCUILMSDSLIGD-OGIIFXRQNA-N
SmilesO=C(C=CC=1C=CC=CC1)C=2C(O)=C(C=3OC4(C)CCC5C(C3C2OC5(C)C)C4)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)7
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)458.596
Computed dipole moment(dipole)6.208
Total solvent accessible surface area (SASA)811.112
Hydrophobic component of SASA (FOSA)501.73
Hydrophilic component of SASA (FISA)77.178
Pie component of the SASA (PISA)232.204
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1511.93
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)3.25
Free energy of solvation of dipole (dip^2/V)0.0254926
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.785426
Predicted polarizability in cubic angstroms (QPpolrz)52.076
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.541
Predicted octanol/gas partition coefficient (QPlogPoct)19.086
Predicted water/gas partition coefficient (QPlogPw)5.433
Predicted octanol/water partition coefficient (QPlogPo/w)7.314
Predicted aqueous solubility (QPlogS)-8.746
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.11
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.111
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1836.62
Predicted brain/blood partition coefficient (QPlogBB)-0.692
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)954.388
Predicted skin permeability, log Kp (QPlogKp)-1.452
PM3 calculated ionization potential (IP(ev))8.88
PM3 calculated electron affinity (EA(eV))0.512
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)1.841
Predicted qualitative human oral absorption (HumanOralAbsorption)1
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)54.986
Number of nitrogen and oxygen atoms (#NandO)4
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P23141CES1Acyl coenzyme A:cholesterol acyltransferaseT76369SwissTargetPrediction
Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
P08183ABCB1P-glycoprotein 1T25258SEA
P07711CTSLCathepsin LT98691SwissTargetPrediction
P07858CTSBCathepsin (B and K)T61746SwissTargetPrediction
P37231PPARGPeroxisome proliferator-activated receptor gammaT58921SwissTargetPrediction
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction
Q9NS75CYSLTR2Cysteinyl leukotriene receptor 2T74238SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T76369DI0335Peroxisomal disease[ICD-11: 5C57]P23141CES1
T76369DI0398Synthesis disorder[ICD-11: 5C52-5C59]P23141CES1
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T61746DI0023Alopecia[ICD-11: ED70]P07858CTSB
T61746DI0025Alzheimer disease[ICD-11: 8A20]P07858CTSB
T61746DI0037Asthma[ICD-11: CA23]P07858CTSB
T61746DI0055Bone cancer[ICD-11: 2B5Z]P07858CTSB
T61746DI0060Brain cancer[ICD-11: 2A00]P07858CTSB
T61746DI0067Cardiac arrest[ICD-11: MC82]P07858CTSB
T61746DI0074Cerebral ischaemic stroke[ICD-11: 8B11]P07858CTSB
T61746DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07858CTSB
T61746DI0087Chronic pain[ICD-11: MG30]P07858CTSB
T61746DI0110Cystic fibrosis[ICD-11: CA25]P07858CTSB
T61746DI0124Digestive system disease[ICD-11: DE2Z]P07858CTSB
T61746DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P07858CTSB
T61746DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P07858CTSB
T61746DI0253Meningioma[ICD-11: 2A01]P07858CTSB
T61746DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P07858CTSB
T61746DI0275Multiple sclerosis[ICD-11: 8A40]P07858CTSB
T61746DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]P07858CTSB
T61746DI0320Osteoarthritis[ICD-11: FA00-FA05]P07858CTSB
T61746DI0351Psoriasis[ICD-11: EA90]P07858CTSB
T61746DI0366Rheumatoid arthritis[ICD-11: FA20]P07858CTSB
T58921DI0009Acute diabete complication[ICD-11: 5A2Y]P37231PPARG
T58921DI0025Alzheimer disease[ICD-11: 8A20]P37231PPARG
T58921DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P37231PPARG
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T74238DI0037Asthma[ICD-11: CA23]Q9NS75CYSLTR2

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