Rescinnamine (CHEM016863)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:45:49 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016863
Identification
Common NameRescinnamine
ClassSmall Molecule
DescriptionRescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from _Rauwolfia serpentina_ and other species of _Rauwolfia_.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methyl trimethoxycinnamoylreserpateHMDB
RecinnamineHMDB
RescinnaminHMDB
ReserpineneHMDB
ReserpininHMDB
ReserpinineHMDB
Trimethoxycinnamoyl methyl reserpateHMDB
Chemical FormulaC35H42N2O9
Average Molecular Mass634.716 g/mol
Monoisotopic Mass634.289 g/mol
CAS Registry Number24815-24-5
IUPAC Namemethyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Traditional Namerescinnamine
SMILES[H][C@]12C[C@@H](OC(=O)C=CC3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=C3C=CC(OC)=C1)C2
InChI IdentifierInChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1
InChI KeySZLZWPPUNLXJEA-LAFLMMDJSA-N
Chemical Taxonomy
Description 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
Substituents
  • 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 Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP4.48ALOGPS
logP4.07ChemAxon
logS-5.3ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007p-0469134000-22e085a00ac52f1a3fc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0033209000-ee873b6b010ae1decc8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-0379405000-82705d2979450611dc45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pj0-3559003000-62945eb088df2981f749Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0031209000-69bd23b15cb07f5f5bc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0i0s-0258429000-07d3b407787494d1c141Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-0549211000-fe6752c4b31c0e6bce52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0042009000-3f55aeb201794c3d5500Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0451019000-95ecd82537f2ede2cae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukd-0931021000-36cc3bd5905e4017f7cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0010009000-4efc2ba750ec5d3d3b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0110094000-9f95afa9be8d5fe523c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056a-1212191000-9673c536103f8fc8f464Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01180
HMDB IDHMDB0015311
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001762
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRescinnamine
Chemspider ID30295
ChEBI ID28572
PubChem Compound ID5280954
Kegg Compound IDC06540
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available