Bovine Metabolome Database: Showing metabocard for Scopolamine (BMDB0003573)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:05:24 UTC

Update Date

2020-05-11 20:30:57 UTC

BMDB ID

BMDB0003573

Secondary Accession Numbers

BMDB03573

Metabolite Identification

Common Name

Scopolamine

Description

Scopolamine, also known as hyoscine or transderm-scop, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Based on a literature review a significant number of articles have been published on Scopolamine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Hyoscine	ChEBI
(-)-Scopolamine	ChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate	ChEBI
6,7-Epoxytropine tropate	ChEBI
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate	ChEBI
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	ChEBI
Hyoscine	ChEBI
Scopine (-)-tropate	ChEBI
Transderm-scop	ChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acid	Generator
6,7-Epoxytropine tropic acid	Generator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropate	Generator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropic acid	Generator
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropic acid	Generator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropate	Generator
6-Β,7-β-epoxy-3-α-tropanyl S-(-)-tropic acid	Generator
a-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
a-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
alpha-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Α-(hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Α-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester	Generator
Scopine (-)-tropic acid	Generator
(+)-Hyoscine	HMDB
(+)-Scopolamine	HMDB
(-)-Hyoscine hydrobromide	HMDB
(-)-Scopolamine bromide	HMDB
(-)-Scopolamine hydrobromide	HMDB
Atrochin	HMDB
Atroquin	HMDB
Beldavrin	HMDB
Buscopan	HMDB
Epoxytropine tropate	HMDB
Euscopol	HMDB
Hydroscine hydrobromide	HMDB
Hyosceine	HMDB
Hyoscine bromide	HMDB
Hyoscine hydrobromide	HMDB
Hyoscyine hydrobromide	HMDB
Hyosol	HMDB
Hysco	HMDB
Isopto hyoscine	HMDB
Isoscopil	HMDB
Kwells	HMDB
L-Hyoscine hydrobromide	HMDB
L-Scopolamine-hydrobromide	HMDB
Methscopolamine bromide	HMDB
Oscine	HMDB
Pamine	HMDB
S-(-)-Tropate	HMDB
Scop	HMDB
Scopamin	HMDB
Scopine tropate	HMDB
Scopolamine bromide	HMDB
Scopolamine hydrobromide	HMDB
Scopolaminium bromide	HMDB
Scopolammonium bromide	HMDB
SEE	HMDB
Tranaxine	HMDB
Norhyoscine	HMDB
6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropate	PhytoBank
6β,7β-Epoxy-3α-tropanyl S-(-)-tropate	PhytoBank
9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol (-)-tropate	PhytoBank
l-Scopolamine	PhytoBank
(-)-Atropine	PhytoBank
(-)-Hyoscyamine	PhytoBank
(S)-(-)-Hyoscyamine	PhytoBank
(S)-Atropine	PhytoBank
1alphaH,5alphaH-Tropan-3alpha-yl (-)-tropate	PhytoBank
1αH,5αH-Tropan-3α-yl (-)-tropate	PhytoBank
Cystospaz	PhytoBank
Daturine	PhytoBank
Duboisine	PhytoBank
Hyoscyamine	PhytoBank
L-Hyoscyamin	PhytoBank
l-Hyoscyamine	PhytoBank
l-Atropine	PhytoBank
l-Tropine tropate	PhytoBank
(±)-Atropine	PhytoBank
(±)-Hyoscyamine	PhytoBank
Atropin	PhytoBank
Atropine	PhytoBank
Atropinum sulfuricum	PhytoBank
Atropinum sulphuricum	PhytoBank
dl-Hyoscyamine	PhytoBank
Tropine (±)-tropate	PhytoBank
Tropine tropate	PhytoBank
dl-Tropyl tropate	PhytoBank

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.3529

Monoisotopic Molecular Weight

303.147058165

IUPAC Name

(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

Traditional Name

(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

CAS Registry Number

51-34-3

SMILES

CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

InChI Key

STECJAGHUSJQJN-FWXGHANASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocyclic benzene moiety
Morpholine
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:16794 )
epoxide (CHEBI:16794 )
propanoate ester (CHEBI:16794 )
tropane alkaloid (CHEBI:16794 )

Ontology

Status

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.4	ALOGPS
logP	0.89	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	6.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.72 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Adipose Tissue
Brain
Epidermis
Neuron

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details