Atropine sulfate

Details

• Internal ID: f53ebabb-588f-47ac-824f-a4a137a2d31a
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate
• SMILES (Canonical): CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• SMILES (Isomeric): CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
• 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,7-11H2,1H3
• InChI Key: RKUNBYITZUJHSG-UHFFFAOYSA-N
• Popularity: 289 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.40 g/mol
• Exact Mass: 289.16779360 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• hyoscyamine
• Atropine sulfate
• Cystospaz
• Hyospaz
• Hyosyne
• Levbid
• Levsin
• l-Atropine
• Symax Duotab
• 1-Hyoscyamine
• Levsinex SR
• Hyoscyamine, l-
• Levsin SL
• Symax SL
• Symax SR
• Daturine (sulfate)
• Hyoscyamine (D)-
• Hyoscyamine [BAN]
• 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol (.+/-.)-tropate (ester)
• 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• R-(+)-Hyoscyamine
• 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, [3(S)-endo]-, sulfate (2:1) (salt)
• L-Hyoscyamine (sulfate)
• Hyoscyamine sulfate
• 2-Phenylhydracrylic Acid 3-A-Tropanyl Ester
• CHEMBL195
• SR-01000075162
• Tropine, (-)-tropate (ester)
• C17H23NO3
• HSDB 3552
• HSDB 3553
• C17H23NO3.1/2H2O4S.1/2H2O
• EINECS 202-933-0
• 620-61-1
• [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
• BRN 0091258
• C17-H23-N-O3.1/2H2-O4-S.1/2H2-O
• Tropic acid, (-)-, ester with tropine
• Benzeneacetic acid, .alpha.-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester
• 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, [3(S)-endo]-
• Atropine,(-)
• Atropisol (Salt/Mix)
• H 9002
• Spectrum_001159
• C17H23NO3.1/2H2O4S
• 1alphaH,5alphaH-Tropan-3alpha-ol (+-)-tropate (ester), sulfate (2:1) (salt) monohydrate
• (.+/-.)-Atropine
• 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol, (.+.)-tropate (ester), sulfate (2:1), hemihydrate
• Benzeneacetic acid, .alpha.-(hydroxymethyl)-, 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, endo-(.+.)-, sulfate (2:1) (salt), hemihydrate
• Prestwick0_000565
• Prestwick1_000565
• Prestwick2_000565
• Prestwick3_000565
• Spectrum2_000094
• Spectrum3_000307
• Spectrum4_001813
• Spectrum5_000545
• (.+/-.)-Hyoscyamine
• UPCMLD-DP018
• 1alphaH,5alphaH-Tropan-3alpha-ol (-)-tropate (ester)
• SCHEMBL2813
• (.+/-.)-Tropyl tropate
• CHEMBL9751
• Lopac0_000042
• Lopac0_000567
• Oprea1_442738
• BSPBio_000350
• BSPBio_001874
• KBioGR_002450
• KBioSS_001639
• 1-alpha H,5-alpha H-tropan-3-alpha-ol (+-)-tropate (ester)
• C17-H23-N-O3.1/2H2-O4-S
• DivK1c_000558
• SPBio_000048
• SPBio_002569
• BPBio1_000386
• UPCMLD-DP018:001
• BDBM86231
• KBio1_000558
• KBio2_001639
• KBio2_004207
• KBio2_006775
• KBio3_001374
• DTXSID00858967
• CHEBI:104243
• NINDS_000558
• HMS3261B16
• HMS3372F19
• HMS3373B22
• HMS3652A17
• L-Hyoscyamine, analytical standard
• (alpha S)-alpha-(Hydroxymethyl)benzeneacetic acid (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
• alpha-(Hydroxymethyl)benzeneacetic acid (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)-, endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (.alpha.S)-
• Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (3(R)-endo)-
• NSC_3661
• Tox21_500567
• BBL033747
• STL374102
• AKOS009031432
• CCG-204138
• LP00567
• SDCCGMLS-0066623.P001
• SDCCGSBI-0050031.P007
• Tropic acid, 3-.alpha.-tropanyl ester
• CAS_51-55-8
• IDI1_000558
• SMP1_000031
• L-Hyoscyamine, >=98% (TLC), powder
• NCGC00015026-03
• NCGC00015026-04
• NCGC00015026-05
• NCGC00015026-06
• NCGC00015026-07
• NCGC00015026-08
• NCGC00015026-09
• NCGC00015026-10
• NCGC00015026-11
• NCGC00015026-12
• NCGC00015026-13
• NCGC00015026-14
• NCGC00015026-21
• NCGC00015026-22
• NCGC00093951-01
• NCGC00093951-02
• NCGC00093951-03
• NCGC00093951-04
• NCGC00094699-01
• NCGC00094699-02
• NCGC00161600-01
• NCGC00161600-02
• NCGC00161600-03
• NCGC00261252-01
• AC-15995
• VS-12248
• SBI-0050031.P005
• 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol, (-)-tropate (ester), sulfate (2:1) (salt)
• A0754
• AB00514677
• CS-0526746
• EU-0100567
• H0450
• D88314
• AB00514677_07
• 2-Phenylhydracrylic acid 3-.alpha.-tropanyl ester
• L001264
• .beta.-Phenyl-.gamma.-oxypropionsaeure-tropyl-ester
• 2-Phenyl-3-hydroxypropionic acid tropane-3-yl ester
• 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropate #
• Q-200659
• SR-01000075162-1
• SR-01000075162-2
• BRD-A93739713-065-03-5
• Q27181620
• SR-01000075162-12
• SR-01000075162-13
• 1.alpha.H,5.alpha.H-Tropan-3.alpha.-ol (.+/-.)-tropate
• 1-.alpha.-H,5-.alpha.-H-Tropan-3-.alpha.-ol (.+/-.)-tropate
• (8-methyl-8-azabicy-clo[3.2.1]oct-3-yl) 3-hydroxy-2-phenylpropanoate
• (8-methyl-8-azabicyclo[3.2.1]oct-3-yl) 3-hydroxy-2-phenyl-propanoate
• 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl alpha-(hydroxymethyl)benzeneacetate
• (S)-alpha-(Hydroxymethyl)benzeneacetic acid (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) ester
• 3-hydroxy-2-phenylpropanoic acid (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) ester
• .alpha.-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-
• 83454-31-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Lysosomes	0.4825	48.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	1.0000	100.00%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9389	93.89%
P-glycoprotein substrate	-	0.7721	77.21%
CYP3A4 substrate	+	0.5662	56.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3762	37.62%
CYP3A4 inhibition	-	0.9500	95.00%
CYP2C9 inhibition	-	0.9275	92.75%
CYP2C19 inhibition	-	0.9285	92.85%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9813	98.13%
CYP inhibitory promiscuity	-	0.9113	91.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6945	69.45%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6189	61.89%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	1.0000	100.00%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8448	84.48%
Acute Oral Toxicity (c)	III	0.7806	78.06%
Estrogen receptor binding	-	0.7539	75.39%
Androgen receptor binding	-	0.6929	69.29%
Thyroid receptor binding	-	0.8320	83.20%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.7444	74.44%
PPAR gamma	+	0.5318	53.18%
Honey bee toxicity	-	0.9334	93.34%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	-	0.5515	55.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	0.44 nM; 0.25 nM; 0.2692 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	0.8128 nM; 0.912 nM; 2.818 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	0.2692 nM; 3.2 nM; 0.5 nM; 0.53 nM	Ki; IC50; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	0.34 nM; 0.64 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	0.14 nM; 0.21 nM; 0.6 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.62%	86.33%
CHEMBL5028	O14672	ADAM10	85.25%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.24%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.57%	97.09%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	84.38%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.45%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.31%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.67%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.19%	82.69%

Plants that contains it

• Anisodus luridus
• Anisodus tanguticus
• Atropa belladonna
• Brugmansia arborea
• Brugmansia aurea
• Brugmansia sanguinea
• Brugmansia suaveolens
• Corydalis decumbens
• Crenidium spinescens
• Cyphanthera myosotidea
• Datura innoxia
• Datura metel
• Datura stramonium
• Datura stramonium
• Duboisia hopwoodii
• Duboisia leichhardtii
• Duboisia myoporoides
• Hyoscyamus albus
• Hyoscyamus muticus
• Hyoscyamus niger
• Hyoscyamus pusillus
• Hyoscyamus reticulatus
• Linum usitatissimum
• Lycium barbarum
• Lycium chinense
• Mandragora officinarum
• Physochlaina alaica
• Scopolia carniolica
• Scopolia japonica
• Solandra grandiflora

Cross-Links

• PubChem: 3661
• NPASS: NPC291027
• LOTUS: LTS0063401
• wikiData: Q27181620