Trichotomine



Compound IDCDAMM02936
Common nameTrichotomine
IUPAC name2-(5-carboxy-3-hydroxy-6,11-dihydro-5H-indolizino[8,7-b]indol-2-yl)-3-oxo-5,6-dihydroindolizino[8,7-b]indole-5-carboxylic acid
Molecular formulaC30H20N4O6

Experimental data

Retention time15.72
Adduct[M+H]+
Actual mz533.148
Theoretical mz533.145
Error4.73
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.9345

Identifiers and class information

Inchi keyLOHPAPKRMNSIDN-PJWPLZPDNA-N
SmilesO=C(O)C1N2C(=O)C(C=C2C=3NC=4C=CC=CC4C3C1)=C5C=C6C=7NC=8C=CC=CC8C7CC(C(=O)O)N6C5=O
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Plant source

  • Clitoria ternatea L.

    • 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)2
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)3
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)532.511
    Computed dipole moment(dipole)8.453
    Total solvent accessible surface area (SASA)811.727
    Hydrophobic component of SASA (FOSA)98.366
    Hydrophilic component of SASA (FISA)280.654
    Pie component of the SASA (PISA)432.706
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1478.32
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)8.5
    Free energy of solvation of dipole (dip^2/V)0.0483284
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.020943
    Globularity descriptor (glob)0.773157
    Predicted polarizability in cubic angstroms (QPpolrz)55.214
    Predicted hexadecane/gas partition coefficient (QPlogPC16)18.067
    Predicted octanol/gas partition coefficient (QPlogPoct)30.541
    Predicted water/gas partition coefficient (QPlogPw)20.094
    Predicted octanol/water partition coefficient (QPlogPo/w)4.125
    Predicted aqueous solubility (QPlogS)-7.147
    Conformation-independent predicted aqueous solubility (CIQPlogS)-8.057
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.651
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.386
    Predicted brain/blood partition coefficient (QPlogBB)-2.747
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.651
    Predicted skin permeability, log Kp (QPlogKp)-4.88
    PM3 calculated ionization potential (IP(ev))8.244
    PM3 calculated electron affinity (EA(eV))2.677
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)0.355
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)40.676
    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)173.149
    Number of nitrogen and oxygen atoms (#NandO)10
    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
    P23280CA6Carbonic anhydrase VIT06569SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P21918DRD5Dopamine D5 receptorT46828SEA
    P52732KIF11Kinesin-like protein 1T28484SEA
    P35346SSTR5Somatostatin receptor 5T64830SEA
    P30874SSTR2Somatostatin receptor 2T53024SEA
    P31391SSTR4Somatostatin receptor 4T62974SEA
    P30872SSTR1Somatostatin receptor 1T16633SEA
    P32745SSTR3Somatostatin receptor 3T13644SEA
    O76074PDE5APhosphodiesterase 5AT07663SEA
    P08151GLI1Zinc finger protein GLI1T40890SEA
    Q9HCN6GP6Platelet glycoprotein VIT60514SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
    T28484DI0012Acute myeloid leukaemia[ICD-11: 2A60]P52732KIF11
    T28484DI0172Head and neck cancer[ICD-11: 2D42]P52732KIF11
    T28484DI0241Lymphoma[ICD-11: 2A80-2A86]P52732KIF11
    T28484DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P52732KIF11
    T28484DI0274Multiple myeloma[ICD-11: 2A83]P52732KIF11
    T28484DI0321Ovarian cancer[ICD-11: 2C73]P52732KIF11
    T28484DI0361Renal cell carcinoma[ICD-11: 2C90]P52732KIF11
    T28484DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P52732KIF11
    T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
    T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
    T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
    T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
    T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
    T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
    T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
    T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
    T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
    T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
    T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
    T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
    T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
    T60514DI0035Arterial occlusive disease[ICD-11: BD40]Q9HCN6GP6
    T60514DI0074Cerebral ischaemic stroke[ICD-11: 8B11]Q9HCN6GP6

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