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Accession NumberDB01180  (APRD00112)
TypeSmall Molecule

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia]

3,4,5-Trimethoxycinnamoyl methyl reserpate
Trimethoxy cinnamoyl reserpate de methyl
Tsuruselpi S
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
Tsuruselpi SNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number24815-24-5
WeightAverage: 634.716
Monoisotopic: 634.289030952
Chemical FormulaC35H42N2O9
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
DescriptionThis compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
  • Yohimbine
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Pyridoindole
  • Beta-carboline
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Phenylpropene
  • Indole or derivatives
  • Indole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
IndicationFor the treatment of hypertension.
PharmacodynamicsUsed to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.
Mechanism of actionRescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption+0.9604
Blood Brain Barrier+0.9248
Caco-2 permeable+0.6805
P-glycoprotein substrateSubstrate0.8163
P-glycoprotein inhibitor IInhibitor0.8826
P-glycoprotein inhibitor IINon-inhibitor0.6553
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8706
CYP450 2D6 substrateNon-substrate0.9064
CYP450 3A4 substrateSubstrate0.7223
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9144
CYP450 3A4 inhibitorNon-inhibitor0.8203
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7162
Ames testNon AMES toxic0.9208
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8345 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.697
hERG inhibition (predictor II)Non-inhibitor0.678
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental Properties
melting point238.5 °CPhysProp
logP3.5Not Available
Predicted Properties
Water Solubility0.00349 mg/mLALOGPS
pKa (Strongest Acidic)16.29ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area117.78 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity171.16 m3·mol-1ChemAxon
Polarizability69.65 Å3ChemAxon
Number of Rings6ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Download (13.2 KB)
SpectraNot Available
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC02AA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.7 KB)
Drug InteractionsNot Available
Food InteractionsNot Available


1. Angiotensin-converting enzyme

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor


Name UniProt ID Details
Angiotensin-converting enzyme P12821 Details


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  3. Azhar I, Mazhar F, Manzar QN, Hussain I, Shamim S: Colorimetric determination of indolic drugs. Pak J Pharm Sci. 2005 Apr;18(2):48-51. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 10, 2014 20:33