Mitragynalinic acid



Compound IDCDAMM02054
Common nameMitragynalinic acid
IUPAC name2-(3-ethyl-1-formyl-8-methoxy-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-ylidene)-3-oxopropanoic acid
Molecular formulaC22H24N2O5

Experimental data

Retention time0.67
Adduct[M+H]+
Actual mz397.178
Theoretical mz397.176
Error3.59
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5241

Identifiers and class information

Inchi keyBZCUJLGQIQXOMA-SDXDJHTJNA-N
SmilesO=CC(C(=O)O)=C1C(C=O)C2C=3NC=4C=CC=C(OC)C4C3CCN2CC1CC
SuperclassAlkaloids and derivatives
ClassCorynanthean-type alkaloids

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)1
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)5
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)396.442
Computed dipole moment(dipole)6.747
Total solvent accessible surface area (SASA)651.948
Hydrophobic component of SASA (FOSA)333.394
Hydrophilic component of SASA (FISA)184.5
Pie component of the SASA (PISA)134.054
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1198.41
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)7.75
Free energy of solvation of dipole (dip^2/V)0.0379815
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0118874
Globularity descriptor (glob)0.83693
Predicted polarizability in cubic angstroms (QPpolrz)39.876
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.823
Predicted octanol/gas partition coefficient (QPlogPoct)19.423
Predicted water/gas partition coefficient (QPlogPw)11.45
Predicted octanol/water partition coefficient (QPlogPo/w)0.561
Predicted aqueous solubility (QPlogS)-3.931
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.753
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.729
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)11.137
Predicted brain/blood partition coefficient (QPlogBB)-1.095
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)5.389
Predicted skin permeability, log Kp (QPlogKp)-6.03
PM3 calculated ionization potential (IP(ev))8.068
PM3 calculated electron affinity (EA(eV))1.169
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.019
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)48.968
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)128.006
Number of nitrogen and oxygen atoms (#NandO)7
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P08173CHRM4Muscarinic acetylcholine receptor M4T20709SEA
P08912CHRM5Muscarinic acetylcholine receptor M5T79961SEA
P08172CHRM2Muscarinic acetylcholine receptor M2T46185SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20709DI0037Asthma[ICD-11: CA23]P08173CHRM4
T20709DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]P08173CHRM4
T20709DI0166Glaucoma[ICD-11: 9C61]P08173CHRM4
T20709DI0293Nausea/vomiting[ICD-11: MD90]P08173CHRM4
T20709DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08173CHRM4
T79961DI0002Abnormal micturition[ICD-11: MF50]P08912CHRM5
T79961DI0032Anterior uveitis[ICD-11: 9A96]P08912CHRM5
T79961DI0034Appearance/behaviour symptom[ICD-11: MB23]P08912CHRM5
T79961DI0037Asthma[ICD-11: CA23]P08912CHRM5
T79961DI0061Brain disease[ICD-11: 8C70-8E61]P08912CHRM5
T79961DI0071Central and peripheral nervous disease[ICD-11: 8A04-8E7Z]P08912CHRM5
T79961DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P08912CHRM5
T79961DI0093Cognition symptoms/signs/clinical symptom[ICD-11: MB21]P08912CHRM5
T79961DI0105Cough[ICD-11: MD12]P08912CHRM5
T79961DI0124Digestive system disease[ICD-11: DE2Z]P08912CHRM5
T79961DI0145Female pelvic pain[ICD-11: GA34]P08912CHRM5
T79961DI0154Functional bladder disorder[ICD-11: GC50]P08912CHRM5
T79961DI0158Gastritis[ICD-11: DA42]P08912CHRM5
T79961DI0162General examination[ICD-11: QA00]P08912CHRM5
T79961DI0166Glaucoma[ICD-11: 9C61]P08912CHRM5
T79961DI0190Hypertension[ICD-11: BA00-BA04]P08912CHRM5
T79961DI0208Infectious gastroenteritis/colitis[ICD-11: 1A40]P08912CHRM5
T79961DI0218Irritable bowel syndrome[ICD-11: DD91]P08912CHRM5
T79961DI0307Nystagmus[ICD-11: 9C84]P08912CHRM5
T79961DI0315Oesophagus motility disorder[ICD-11: DA21]P08912CHRM5
T79961DI0324Pain[ICD-11: MG30-MG3Z]P08912CHRM5
T79961DI0329Pancreatitis[ICD-11: DC31-DC34]P08912CHRM5
T79961DI0331Parkinsonism[ICD-11: 8A00]P08912CHRM5
T79961DI0333Peptic ulcer[ICD-11: DA61]P08912CHRM5
T79961DI0338Polyuria[ICD-11: MF55]P08912CHRM5
T79961DI0411Tonus and reflex abnormality[ICD-11: MB47]P08912CHRM5
T79961DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P08912CHRM5
T79961DI0424Urgency[ICD-11: N.A.]P08912CHRM5
T46185DI0037Asthma[ICD-11: CA23]P08172CHRM2
T46185DI0166Glaucoma[ICD-11: 9C61]P08172CHRM2
T46185DI0278Muscle disorder[ICD-11: FB32-FB3Z]P08172CHRM2
T46185DI0333Peptic ulcer[ICD-11: DA61]P08172CHRM2
T46185DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08172CHRM2
T46185DI0371Sebaceous gland disorder[ICD-11: ED91]P08172CHRM2

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