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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015221
Secondary Accession Numbers
  • HMDB15221
Metabolite Identification
Common NameDeserpidine
DescriptionDeserpidine is only found in individuals that have used or taken this drug. It is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.Deserpidine's mechanism of action is through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.
Structure
Data?1582753272
Synonyms
ValueSource
(3beta,16beta,17alpha,18beta,20alpha)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl esterChEBI
11-DemethoxyreserpineChEBI
11-DesmethoxyreserpineChEBI
CanescineChEBI
HarmonylChEBI
RaunormineChEBI
RecanescineChEBI
HalmonylKegg
(3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl esterGenerator
(3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl esterGenerator
(3beta,16beta,17alpha,18beta,20alpha)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl esterGenerator
(3Β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl esterGenerator
(3Β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl esterGenerator
DeresperineHMDB
DesepridineHMDB
DeserpidinHMDB
DeserpineHMDB
DesmethoxyreserpineHMDB
Chemical FormulaC32H38N2O8
Average Molecular Weight578.6527
Monoisotopic Molecular Weight578.262816202
IUPAC Namemethyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
Traditional Namedeserpidine
CAS Registry Number131-01-1
SMILES
[H][C@]12C[C@@H](OC(=O)C3=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=CC=CC=C31)C2
InChI Identifier
InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
InChI KeyCVBMAZKKCSYWQR-WCGOZPBSSA-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
  • Gallic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • Benzoate ester
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Piperidine
  • Pyrrole
  • Methyl ester
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Tertiary amine
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Azacycle
  • Dialkyl ether
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.011 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.25ALOGPS
logP3.69ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.37ChemAxon
pKa (Strongest Basic)7.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity154.96 m³·mol⁻¹ChemAxon
Polarizability62.59 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
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]-254.90130932474
DeepCCS[M+Na]+228.73730932474
AllCCS[M+H]+236.432859911
AllCCS[M+H-H2O]+235.132859911
AllCCS[M+NH4]+237.632859911
AllCCS[M+Na]+238.032859911
AllCCS[M-H]-231.932859911
AllCCS[M+Na-2H]-234.232859911
AllCCS[M+HCOO]-237.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Deserpidine[H][C@]12C[C@@H](OC(=O)C3=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=CC=CC=C31)C25531.6Standard polar33892256
Deserpidine[H][C@]12C[C@@H](OC(=O)C3=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=CC=CC=C31)C24176.8Standard non polar33892256
Deserpidine[H][C@]12C[C@@H](OC(=O)C3=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=CC=CC=C31)C24582.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deserpidine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C4441.4Semi standard non polar33892256
Deserpidine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C4348.7Standard non polar33892256
Deserpidine,1TMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C6061.3Standard polar33892256
Deserpidine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C4579.2Semi standard non polar33892256
Deserpidine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C4512.7Standard non polar33892256
Deserpidine,1TBDMS,isomer #1COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C6029.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Deserpidine EI-B (Non-derivatized)splash10-014i-7967010000-b3758c647fba3c682e472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deserpidine EI-B (Non-derivatized)splash10-014i-7967010000-b3758c647fba3c682e472018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deserpidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0849160000-31b897a373d9e518c58c2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 10V, Positive-QTOFsplash10-004i-0002090000-d380a4874665812fb77b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 20V, Positive-QTOFsplash10-016s-0204090000-c1fc5fd8f24bc1d1a6802016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 40V, Positive-QTOFsplash10-0a4i-9648240000-1c2d515bf3c44bf027212016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 10V, Negative-QTOFsplash10-004i-0010090000-2a2e2e1b10901bf78f482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 20V, Negative-QTOFsplash10-0401-0211090000-9dd997b03213bc3fd9262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 40V, Negative-QTOFsplash10-01t9-2930110000-34d5246da664b17987662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 10V, Positive-QTOFsplash10-004i-0101090000-f6f633c332e0a14be0b82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 20V, Positive-QTOFsplash10-004j-0512090000-8682dbe8aa29a53b97e22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 40V, Positive-QTOFsplash10-052p-2809220000-943412432c84f8ba87812021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 10V, Negative-QTOFsplash10-004i-0010090000-3aa6450ab246b9e4e0cb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 20V, Negative-QTOFsplash10-02wa-0100190000-e4cb0c7a1c4dd472e6e82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deserpidine 40V, Negative-QTOFsplash10-0gw1-1210960000-3407791d5c914c80a9992021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01089 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01089 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01089
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001712
Chemspider ID8232
KEGG Compound IDC06541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeserpidine
METLIN IDNot Available
PubChem Compound8550
PDB IDNot Available
ChEBI ID27478
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 transmembrane transport
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
References
  1. Sievert MK, Hajipour AR, Ruoho AE: Specific derivatization of the vesicle monoamine transporter with novel carrier-free radioiodinated reserpine and tetrabenazine photoaffinity labels. Anal Biochem. 2007 Aug 1;367(1):68-78. Epub 2007 May 3. [PubMed:17559790 ]
  2. Naudon L, Leroux-Nicollet I, Raisman-Vozari R, Botton D, Costentin J: Time-course of modifications elicited by reserpine on the density and mRNA synthesis of the vesicular monoamine transporter, and on the density of the membrane dopamine uptake complex. Synapse. 1995 Sep;21(1):29-36. [PubMed:8525459 ]
  3. Erickson JD, Eiden LE, Hoffman BJ: Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10993-7. [PubMed:1438304 ]
  4. Mandela P, Chandley M, Xu YY, Zhu MY, Ordway GA: Reserpine-induced reduction in norepinephrine transporter function requires catecholamine storage vesicles. Neurochem Int. 2010 May-Jun;56(6-7):760-7. doi: 10.1016/j.neuint.2010.02.011. Epub 2010 Feb 20. [PubMed:20176067 ]
  5. Fulton SC, Healy MD: Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62. [PubMed:11134 ]
  6. Loeffler LJ, Schran HF: Antibody specificity studies for reserpine, its metabolites, and synthetic reserpine congeners: radioimmunoassay. J Pharm Sci. 1979 Nov;68(11):1433-5. [PubMed:574544 ]