Showing Compound Pseudoecgonine (FDB023899)

Record Information

Version

1.0

Creation date

2011-09-21 00:36:34 UTC

Update date

2015-07-21 06:57:55 UTC

Primary ID

FDB023899

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pseudoecgonine

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). [HMDB]

CAS Number

Not Available

Structure

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

Synonyms

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Synonym	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-carboxylate	hmdb
(2S,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB
(2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	hmdb
D-Pseudoecgonine	HMDB
d-Pseudoecgonine	hmdb
D-Psi-ecgonine	HMDB
d-psi-Ecgonine	hmdb
delta-Pseudoecgonine	HMDB

Showing 1 to 10 of 15 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H15NO3

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

185.2203

Monoisotopic Molecular Weight

185.105193351

Classification

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 )

Ontology

Disposition

Biological location:

Subcellular:

Endoplasmic reticulum

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pseudoecgonine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001j-9200000000-48c3b8ee572b2dc52292	Spectrum
Predicted GC-MS	Pseudoecgonine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-9132000000-9a8887ca9dce4b08af81	Spectrum
Predicted GC-MS	Pseudoecgonine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-84cf8248e17a8b226247	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0900000000-ada9e3b58a4a68bf34fe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-3900000000-4fe8aa09d75ccea8cb33	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-007o-0900000000-c8352412d369827945bc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0900000000-143c9c6dc9126fa654dc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-1900000000-cb49be4d17eb1921ff3e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-4a6fc2f9a39f6a7a3d44	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kv-5900000000-a2ec3ebcb3ee1f393d9b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-9700000000-ac3cdeb9ee66f2c193db	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-0900000000-dc9636670e82e30cec7c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007o-1900000000-5cbac175885e0c570c49	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-6900000000-987da97e182a8b3e0ba9	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

391940

ChEMBL ID

Not Available

KEGG Compound ID

C12449

Pubchem Compound ID

443845

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06348

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

2282520

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Pseudoecgonine (FDB023899)

Structure for FDB023899 (Pseudoecgonine)