Molecular Details

DICL_CP_0324920 - [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

Basic Molecular Information

Basic Information

DICL ID

DICL_CP_0324920

PubChem CID

174174

Molecular Formula

C₁₇H₂₃NO₃

Molecular Weight

289.375 g/mol

Synonyms/Alias

[ATROPINE; dl-Hyoscyamine; 51-55-8; Tropine tropate; Atropen; Atropin; dl-Tropyltropate; Atropinol; Eyesules; Isopto-atropine; Troyl tropate; hyoscyamine; Atropina; Atropin-flexiolen; (+;-)-Tropyl tro...[ATROPINE; dl-Hyoscyamine; 51-55-8; Tropine tropate; Atropen; Atropin; dl-Tropyltropate; Atropinol; Eyesules; Isopto-atropine; Troyl tropate; hyoscyamine; Atropina; Atropin-flexiolen; (+;-)-Tropyl tropate; Atropin [German]; Atropina [Italian]; (+-)-hyoscyamine; Tropine; tropate (ester); (+-)-atropine; Tropic acid; ester with tropine; (+/-)-Atropine; (+/-)-Hyoscyamine; CCRIS 3080; Atropine (USP); Atropine sulfate; Tropic acid; 3-alpha-tropanyl ester; Atropinum; HSDB 2199; DL-Tropanyl 2-hydroxy-1-phenylpropionate; 2-Phenylhydracrylic acid 3-alpha-tropanyl ester; AI3-60219; beta-Phenyl-gamma-oxypropionsaure-tropyl-ester [German]; DL-Tropyl tropate; (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate; 1alphaH;5alphaH-Tropan-3alpha-ol (+-)-tropate (ester); beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester [German]; (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropate; tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate; 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropate; MLS000069795; Tropine tropate;DL-Hyoscyamine; DTXSID4020113; CHEBI:16684; 7C0697DR9I; 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate; [(1S;5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoate; endo-(+/-)-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; Benzeneacetic acid; alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3;2;1)oct-3-yl ester; endo-(+-)-; NCGC00017333-03; SMR000058248; alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; AB00694549-11; Benzeneacetic acid; alpha-(hydroxymethyl)-; 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; endo-(+-)-; DTXCID20113; CAS-51-55-8; Atropen (TN); Protamine & Atropine; Atropine [USP:BAN]; 5908-99-6; EINECS 200-104-8; Tropine (+/-)-tropate; ropine tropate; UNII-7C0697DR9I; (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL TROPATE; NCGC00159345-02; 3-tropoyloxytropane; 1-alpha-H;5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester); ATROPINE [MI]; ATROPINE [VANDF]; ATROPINUM [HPUS]; Opera_ID_1088; ATROPINE [MART.]; beta-Phenyl-gamma-oxypropionsaure-tropyl-ester; ATROPINE [USP-RS]; ATROPINE [WHO-DD]; bmse000649; beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester; SCHEMBL2812; [(1R;5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; Atropine; analytical standard; GTPL320; Benzeneacetic acid; alpha-(hydroxymethyl)-; (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; MLS001148094; MLS002695888; ATROPINE [GREEN BOOK]; ATNAA COMPONENT ATROPINE; ATROPINE [EP IMPURITY]; ATROPINE [ORANGE BOOK]; CHEMBL254656; CHEMBL475124; CHEMBL517712; cid_174174; MEGxp0_001878; Atropine ((+/-)-Hyoscyamin); ATROPINE [EP MONOGRAPH]; ATROPINE [USP MONOGRAPH]; ATROPINE; (+/-)-; SCHEMBL26698079; ACon1_000046; CHEBI:78734; DUODOTE COMPONENT ATROPINE; (1R;3r;5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate; ATROPINE ((+/-)-); Atropine; >=95.0% (NT); RKUNBYITZUJHSG-PJPHBNEVSA-N; BDBM200229; DTXSID601141720; HMS2089A16; HMS2231G17; HMS3259M13; BCP15060; HY-B1205; Atropine; >=99% (TLC); powder; Tox21_110816; Tox21_111590; Tox21_200487; 1-alpha-H;5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI); BDBM50403547; MFCD00022622; s4713; AKOS015955538; CS-4834; DB00572; NC00493; NCGC00017333-02; NCGC00017333-04; NCGC00017333-05; NCGC00017333-06; NCGC00142514-01; NCGC00142514-03; NCGC00258041-01; NCGC00385525-01; AS-56020; Benzeneacetic acid; alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; endo-(+-)-; Atropine; meets USP testing specifications; C1504; C01479; D00113; Q26272; AB00694549-12; AB00694549_14; rac-tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate; BRD-A27290375-001-01-8; BRD-A27290375-330-01-1; Atropine; European Pharmacopoeia (EP) Reference Standard; HOMATROPINE HYDROBROMIDE IMPURITY D [EP IMPURITY]; 1.ALPHA.H;5.ALPHA.H-TROPAN-3.ALPHA.-OL (+/-)-TROPATE (ESTER); (3-exo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl I+/--(hydroxymethyl)benzeneacetate; [(1R;5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate; [(1S;5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate; Atropine for peak identification; European Pharmacopoeia (EP) Reference Standard; rac-(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate; 16175-85-2; BENZENEACETIC ACID; .ALPHA.-(HYDROXYMETHYL)-(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER; BENZENEACETIC ACID; .ALPHA.-(HYDROXYMETHYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER; ENDO-(+/-)-; Benzeneacetic acid; alpha-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; Benzeneacetic acid; alpha-(hydroxymethyl)-; 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester; endo-(+/-)-; Benzeneacetic acid; alpha-(hydroxymethyl)-8-methyl-8-azabicyclo [3.2.1]oct-3-yl ester; endo-(+/-)-]

InChI Key

RKUNBYITZUJHSG-PJPHBNEVSA-N

InChI

InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-...

IUPAC Name

[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

CAS Number

101-31-5

Structure Information

Chemical Structure Visualization

SMILES Notation

2D Molecular Drawing

Carbon (C)

Hydrogen (H)

Oxygen (O)

Nitrogen (N)

Sulfur (S)

SDF

44 46 0 0 0 0 0 0 0 0999 V2000
4.6836 1.3139 -1.5288 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3843 0.6652 -1.2762 N 0 0 0 0 0 0 0 0 0 0 0 0
2.3936 1.590...

Download SDF File (3755 bytes)

Experimental Data

Activity Data

Target Ion Channel

Neuronal acetylcholine receptor subunit alpha-3/beta-4

Uniprot Accession Number

Q07263/Q8SPU6

Function

Antagonist

Species

Bos taurus (Bovine)

IC₅₀

IC₅₀: 46 nM

EC₅₀

N/A (Not available)

K_i

N/A (Not available)

K_d

N/A (Not available)

Inhibition

N/A (Not available)

Experimental Conditions

pH 7.4

Holding Potential

−80 mV mV

Temperature

22–24 °C

Test Method

Patch-clamping

Test Species

Xenopus laevis oocyte

Binding Information

Binding Site

Not specified

Binding Site Residue

Not specified

Disease Information

Related Disease

Not specified

References

DOI

10.1016/j.ejphar.2006.01.057

URL

N/A (Not available)

PMID

16530180

Patent

N/A (Not available)

Computed Properties

Heavy Atom Count

Rotatable Bonds

logP

1.9309

Complexity

79.9558

TPSA (Å²)

49.77

H-Bond Donors

H-Bond Acceptors

Ring Count

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