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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-12-07 02:50:20 UTC
Secondary Accession Numbers
  • HMDB15311
Metabolite Identification
Common NameRescinnamine
DescriptionRescinnamine is only found in individuals that have used or taken this drug. It 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]Rescinnamine 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.
Methyl trimethoxycinnamoylreserpateHMDB
Trimethoxycinnamoyl methyl reserpateHMDB
Chemical FormulaC35H42N2O9
Average Molecular Weight634.716
Monoisotopic Molecular Weight634.289030952
IUPAC Namemethyl (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
Traditional Namerescinnamine
CAS Registry Number24815-24-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassYohimbine alkaloids
Direct ParentYohimbine alkaloids
Alternative Parents
  • Yohimbine
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Pyridoindole
  • Beta-carboline
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Styrene
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Fatty acid ester
  • Alkyl aryl ether
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Piperidine
  • Fatty acyl
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Pyrrole
  • Tertiary amine
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Dialkyl ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Biological Location:


  Biofluid and excreta:

  Cell and elements:


Naturally occurring process:

  Biological process:

    Biochemical pathway:


Industrial application:

  Pharmaceutical industry:

    Cardiovascular drug:

Physical Properties
Experimental Properties
Melting Point238.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 g/LNot Available
LogP3.5Not Available
Predicted Properties
Water Solubility0.0035 g/LALOGPS
pKa (Strongest Acidic)16.29ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area117.78 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity171.16 m³·mol⁻¹ChemAxon
Polarizability69.65 ųChemAxon
Number of Rings6ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007p-0469134000-22e085a00ac52f1a3fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0033209000-ee873b6b010ae1decc8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-0379405000-82705d2979450611dc45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pj0-3559003000-62945eb088df2981f749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0031209000-69bd23b15cb07f5f5bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i0s-0258429000-07d3b407787494d1c141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-0549211000-fe6752c4b31c0e6bce52View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Rescinnamine PathwayPw000233Pw000233 greyscalePw000233 simpleNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01180 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01180 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01180
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444446
KEGG Compound IDC06540
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRescinnamine
METLIN IDNot Available
PubChem Compound5280954
PDB IDNot Available
ChEBI ID28572
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in metallopeptidase activity
Specific function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
Uniprot ID:
Molecular weight:
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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:16431399 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]