ContaminantDB: Pseudoecgonine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 07:13:39 UTC

Update Date

2016-11-09 01:21:26 UTC

Accession Number

CHEM036081

Identification

Common Name

Pseudoecgonine

Class

Small Molecule

Description

Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+)-Pseudoecgonine	HMDB
(2S,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	HMDB
(2S,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB
D-Pseudoecgonine	HMDB
D-Psi-ecgonine	HMDB
delta-Pseudoecgonine	HMDB
delta-Psi-ecgonine	HMDB
pseudo-Ecgonine	HMDB

Chemical Formula

C₉H₁₅NO₃

Average Molecular Mass

185.220 g/mol

Monoisotopic Mass

185.105 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Traditional Name

pseudoecgonine

SMILES

CN1C2CCC1[C@@H]([C@@H](O)C2)C(O)=O

InChI Identifier

InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8-/m0/s1

InChI Key

PHMBVCPLDPDESM-GHNGIAPOSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Piperidinecarboxylic acid
Tropane alkaloid
Beta-hydroxy acid
Hydroxy acid
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Amino acid or derivatives
Amino acid
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Amine
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tropane alkaloid (CHEBI:32072 )
Tropane alkaloids (C12449 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1050 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-3.1	ChemAxon
logS	0.75	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.57 m³·mol⁻¹	ChemAxon
Polarizability	18.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-48c3b8ee572b2dc52292	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006t-9132000000-9a8887ca9dce4b08af81	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-84cf8248e17a8b226247	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0900000000-ada9e3b58a4a68bf34fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-3900000000-4fe8aa09d75ccea8cb33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-007o-0900000000-c8352412d369827945bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0900000000-143c9c6dc9126fa654dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-1900000000-cb49be4d17eb1921ff3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-4a6fc2f9a39f6a7a3d44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kv-5900000000-a2ec3ebcb3ee1f393d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-9700000000-ac3cdeb9ee66f2c193db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-0900000000-dc9636670e82e30cec7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007o-1900000000-5cbac175885e0c570c49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-6900000000-987da97e182a8b3e0ba9	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum