Machaeriol A



Compound IDCDAMM02862
Common nameMachaeriol A
IUPAC name6,6,9-trimethyl-3-(2-phenylethenyl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
Molecular formulaC24H28O2

Experimental data

Retention time28.2
Adduct[M+H]+
Actual mz349.221
Theoretical mz349.216
Error12.67
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5307

Identifiers and class information

Inchi keyKCNFZTIIENBEPU-GJNWLAOBNA-N
SmilesOC1=CC(C=CC=2C=CC=CC2)=CC=3OC(C)(C)C4CCC(C)CC4C13
SuperclassPhenylpropanoids and polyketides
ClassStilbenes

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)4
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)348.484
Computed dipole moment(dipole)1.162
Total solvent accessible surface area (SASA)670.548
Hydrophobic component of SASA (FOSA)336.737
Hydrophilic component of SASA (FISA)37.451
Pie component of the SASA (PISA)296.36
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1198.05
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)1.5
Free energy of solvation of dipole (dip^2/V)0.0011266
Index of cohesive interaction in solids (ACxDN^.5/SA)0.002237
Globularity descriptor (glob)0.813552
Predicted polarizability in cubic angstroms (QPpolrz)42.054
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.934
Predicted octanol/gas partition coefficient (QPlogPoct)15.78
Predicted water/gas partition coefficient (QPlogPw)5.663
Predicted octanol/water partition coefficient (QPlogPo/w)6.268
Predicted aqueous solubility (QPlogS)-7.309
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.423
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.962
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4372.72
Predicted brain/blood partition coefficient (QPlogBB)-0.055
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2437.4
Predicted skin permeability, log Kp (QPlogKp)-0.782
PM3 calculated ionization potential (IP(ev))8.624
PM3 calculated electron affinity (EA(eV))0.559
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)1.437
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)26.439
Number of nitrogen and oxygen atoms (#NandO)2
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
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction and SEA
P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P28845HSD11B111-beta-hydroxysteroid dehydrogenase 1T65200SwissTargetPrediction
P16662UGT2B7UDP-glucuronosyltransferase 2B7T62815SEA
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P43116PTGER2Prostanoid EP2 receptorT38529SwissTargetPrediction
Q13418ILKSerine/threonine-protein kinase ILK-1T13616SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction and SEA
P35408PTGER4Prostanoid EP4 receptorT18876SwissTargetPrediction
P56373P2RX3P2X purinoceptor 3T17140SwissTargetPrediction
Q96GD4AURKBSerine/threonine-protein kinase Aurora-BT46781SwissTargetPrediction
P25116F2RProteinase-activated receptor 1T36483SwissTargetPrediction
Q14330GPR18N-arachidonyl glycine receptorT72267SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
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
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T65200DI0210Influenza[ICD-11: 1E30-1E32]P28845HSD11B1
T65200DI0239Lupus erythematosus[ICD-11: 4A40]P28845HSD11B1
T65200DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P28845HSD11B1
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T13616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q13418ILK
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T17140DI0105Cough[ICD-11: MD12]P56373P2RX3
T46781DI0009Acute diabete complication[ICD-11: 5A2Y]Q96GD4AURKB
T46781DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96GD4AURKB
T36483DI0287Myocardial infarction[ICD-11: BA41-BA43]P25116F2R

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