Rescinnamine



Compound IDCDAMM00650
Common nameRescinnamine
IUPAC namemethyl 6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Molecular formulaC35H42N2O9

Experimental data

Retention time2.79
Adduct[M+Na]+
Actual mz657.285
Theoretical mz657.278
Error10.77
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9215

Identifiers and class information

Inchi keySZLZWPPUNLXJEA-LAFLMMDJSA-N
SmilesO=C(OC1CC2CN3CCC=4C=5C=CC(OC)=CC5NC4C3CC2C(C(=O)OC)C1OC)C=CC6=CC(OC)=C(OC)C(OC)=C6
SuperclassAlkaloids and derivatives
ClassYohimbine alkaloids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    Number of non-conjugated amine groups (#amine)1
    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)10
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)1
    Molecular weight (mol_MW)634.725
    Computed dipole moment(dipole)5.916
    Total solvent accessible surface area (SASA)958.706
    Hydrophobic component of SASA (FOSA)726.789
    Hydrophilic component of SASA (FISA)61.779
    Pie component of the SASA (PISA)170.138
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1868.42
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)10.7
    Free energy of solvation of dipole (dip^2/V)0.018734
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0111609
    Globularity descriptor (glob)0.765238
    Predicted polarizability in cubic angstroms (QPpolrz)63.824
    Predicted hexadecane/gas partition coefficient (QPlogPC16)17.566
    Predicted octanol/gas partition coefficient (QPlogPoct)28.341
    Predicted water/gas partition coefficient (QPlogPw)13.402
    Predicted octanol/water partition coefficient (QPlogPo/w)5.714
    Predicted aqueous solubility (QPlogS)-6.649
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.655
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.868
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)641.129
    Predicted brain/blood partition coefficient (QPlogBB)-0.344
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)338.502
    Predicted skin permeability, log Kp (QPlogKp)-3.161
    PM3 calculated ionization potential (IP(ev))8.011
    PM3 calculated electron affinity (EA(eV))0.822
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)1.055
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)71.764
    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)112.434
    Number of nitrogen and oxygen atoms (#NandO)11
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    P18825ADRA2CAdrenergic receptor alpha-2T01777SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P18089ADRA2BAlpha-2b adrenergic receptorT41580SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    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
    T41580DI0396Substance abuse[ICD-11: 6C40]P18089ADRA2B
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
    T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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