Licorisoflavan A



Compound IDCDAMM01473
Common nameLicorisoflavan A
IUPAC name4-[5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
Molecular formulaC27H34O5

Experimental data

Retention time12.75
Adduct[M+H]+
Actual mz439.254
Theoretical mz439.248
Error13.03
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0669

Identifiers and class information

Inchi keyGDAAEAXMNLVRCZ-UHFFFAOYNA-N
SmilesOC1=CC=C(C(O)=C1CC=C(C)C)C2COC3=CC(OC)=C(C(OC)=C3C2)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassIsoflavonoids

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)8
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)438.563
Computed dipole moment(dipole)2.952
Total solvent accessible surface area (SASA)778.665
Hydrophobic component of SASA (FOSA)578.542
Hydrophilic component of SASA (FISA)59.896
Pie component of the SASA (PISA)140.228
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1443.78
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.75
Free energy of solvation of dipole (dip^2/V)0.0060378
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0068108
Globularity descriptor (glob)0.793379
Predicted polarizability in cubic angstroms (QPpolrz)47.828
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.56
Predicted octanol/gas partition coefficient (QPlogPoct)20.255
Predicted water/gas partition coefficient (QPlogPw)7.813
Predicted octanol/water partition coefficient (QPlogPo/w)6.34
Predicted aqueous solubility (QPlogS)-7.585
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.296
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.544
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2678.61
Predicted brain/blood partition coefficient (QPlogBB)-0.553
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1435.06
Predicted skin permeability, log Kp (QPlogKp)-1.361
PM3 calculated ionization potential (IP(ev))8.664
PM3 calculated electron affinity (EA(eV))-0.122
Number of likely metabolic reactions (#metab)12
Prediction of binding to human serum albumin (QPlogKhsa)1.392
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)60.449
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P47869GABRA2GABA A receptor alpha-2/beta-2/gamma-2T51452SwissTargetPrediction
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P08913ADRA2AAlpha-2a adrenergic receptorT11448SEA
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction and SEA
P21728DRD1Dopamine D1 receptorT22118SEA
P21918DRD5Dopamine D5 receptorT46828SEA
P18825ADRA2CAdrenergic receptor alpha-2T01777SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P78536ADAM17ADAM17T82393SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction and SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
O60911CTSVCathepsin (V and K)T93653SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T51452DI0216Intentional self-harm[ICD-11: PC91]P47869GABRA2
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T22118DI0003Abortion[ICD-11: JA00]P21728DRD1
T22118DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21728DRD1
T22118DI0190Hypertension[ICD-11: BA00-BA04]P21728DRD1
T22118DI0331Parkinsonism[ICD-11: 8A00]P21728DRD1
T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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