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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015311
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.
Structure
Data?1582753282
Synonyms
ValueSource
Methyl trimethoxycinnamoylreserpateHMDB
RecinnamineHMDB
RescinnaminHMDB
ReserpineneHMDB
ReserpininHMDB
ReserpinineHMDB
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[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Traditional Namerescinnamine
CAS Registry Number24815-24-5
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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point238.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 g/LNot Available
LogP3.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-260.77730932474
DeepCCS[M+Na]+234.56730932474
AllCCS[M+H]+248.932859911
AllCCS[M+H-H2O]+247.932859911
AllCCS[M+NH4]+249.832859911
AllCCS[M+Na]+250.032859911
AllCCS[M-H]-241.332859911
AllCCS[M+Na-2H]-244.532859911
AllCCS[M+HCOO]-248.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Rescinnamine[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)C26144.6Standard polar33892256
Rescinnamine[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)C24670.9Standard non polar33892256
Rescinnamine[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)C25190.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rescinnamine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C4893.5Semi standard non polar33892256
Rescinnamine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C4811.0Standard non polar33892256
Rescinnamine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C6756.2Standard polar33892256
Rescinnamine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C5025.0Semi standard non polar33892256
Rescinnamine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C4988.0Standard non polar33892256
Rescinnamine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C6665.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rescinnamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-007p-0469134000-22e085a00ac52f1a3fc42017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 10V, Positive-QTOFsplash10-0079-0033209000-ee873b6b010ae1decc8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 20V, Positive-QTOFsplash10-00xs-0379405000-82705d2979450611dc452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 40V, Positive-QTOFsplash10-0pj0-3559003000-62945eb088df2981f7492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 10V, Negative-QTOFsplash10-001i-0031209000-69bd23b15cb07f5f5bc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 20V, Negative-QTOFsplash10-0i0s-0258429000-07d3b407787494d1c1412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 40V, Negative-QTOFsplash10-000t-0549211000-fe6752c4b31c0e6bce522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 10V, Positive-QTOFsplash10-0079-0042009000-3f55aeb201794c3d55002021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 20V, Positive-QTOFsplash10-0079-0451019000-95ecd82537f2ede2cae92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 40V, Positive-QTOFsplash10-0ukd-0931021000-36cc3bd5905e4017f7cf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 10V, Negative-QTOFsplash10-001i-0010009000-4efc2ba750ec5d3d3b4e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 20V, Negative-QTOFsplash10-00dr-0110094000-9f95afa9be8d5fe523c32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rescinnamine 40V, Negative-QTOFsplash10-056a-1212191000-9673c536103f8fc8f4642021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01180 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01180 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01180
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001762
Chemspider ID30295
KEGG Compound IDC06540
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRescinnamine
METLIN IDNot Available
PubChem Compound5280954
PDB IDNot Available
ChEBI ID28572
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  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 ]