Homatropine

Details

• Internal ID: 79de5d8a-2af6-492a-a264-3f0724751b0a
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-hydroxy-2-phenylacetate
• SMILES (Canonical): CN1C2CCC1CC(C2)OC(=O)C(C3=CC=CC=C3)O
• SMILES (Isomeric): CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(C3=CC=CC=C3)O
• InChI: InChI=1S/C16H21NO3/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13+,14?,15?
• InChI Key: ZTVIKZXZYLEVOL-DGKWVBSXSA-N
• Popularity: 1,199 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34 g/mol
• Exact Mass: 275.15214353 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 87-00-3
• Mandelyltropeine
• Homatropin
• Omatropina
• Methylhomatropinum
• Homoatropine
• Omatropina [DCIT]
• 3alpha-Tropylmandelat
• Tropinmandelsaeureester
• DL-HOMATROPINE
• Homatropine [INN:BAN]
• DL-Mandelsaeure-tropylester
• UNII-8QS6WCL55Z
• Tropine, mandelate (ester)
• 8QS6WCL55Z
• Homotropine
• Mandelytropeine
• CHEBI:5747
• tropine mandelate
• DTXSID6044014
• C16H21NO3
• EINECS 201-716-8
• (+/-)-Homatropine
• BRN 0087959
• (+/-)-Mandelyltropine
• (RS)-3alpha(1alphaH,5alphaH)-Tropanylmandelat
• 5-21-01-00234 (Beilstein Handbook Reference)
• 1aH,3aH-Tropan-3a-ol mandelate (ester) hydrobromide
• HOMATROPINE SULFATE
• Mandelic acid, 3d-tropanyl ester
• Homatropine [BAN]
• Benzeneacetic acid, a-hydroxy-,(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
• NCGC00179630-03
• homatropin-
• s ethyl
• (+-)-Homatropine
• HOMATROPINE [MI]
• Prestwick0_000062
• Prestwick1_000062
• Prestwick2_000062
• Prestwick3_000062
• [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-hydroxy-2-phenylacetate
• HOMATROPINE [VANDF]
• 1-alpha-H,5-alpha-H-Tropan-3-alpha-ol, mandelate (ester)
• HOMATROPINE [MART.]
• SCHEMBL23969
• BSPBio_000243
• HOMATROPINE [WHO-DD]
• SPBio_002164
• BPBio1_000269
• MEGxp0_001876
• CHEMBL1618018
• SCHEMBL15275620
• ACon1_000253
• CHEBI:91858
• DTXCID00809535
• DTXSID00858826
• (1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate
• HY-B0547
• Tox21_113104
• AC-1301
• DB11181
• CAS-87-00-3
• NCGC00179630-01
• NCGC00179630-02
• PD006610
• CS-0009509
• C07814
• AB00694561_08
• 1-alpha H,5-alpha H-tropan-3-alpha-ol mandelate
• EN300-18536062
• Q1038115
• BRD-A74975734-004-02-4
• BRD-A74975734-004-10-7
• HOMATROPINE HYDROBROMIDE IMPURITY A [EP IMPURITY]
• HOMATROPINE METHYLBROMIDE IMPURITY B [EP IMPURITY]
• (3-exo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl hydroxy(phenyl)acetate
• [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-hydroxy-2-phenylacetate
• alpha-Hydroxybenzeneacetic acid (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3alpha-yl ester
• alpha-Hydroxybenzeneacetic acid (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
• BENZENEACETIC ACID, .ALPHA.-HYDROXY-, 8-METHYL-8-AZABICYCLO(.2.1)OCT-3-YL ESTER
• 16175-57-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9713	97.13%
Caco-2	+	0.8443	84.43%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5272	52.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9592	95.92%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.9000	90.00%
BSEP inhibitior	-	0.9334	93.34%
P-glycoprotein inhibitior	-	0.9203	92.03%
P-glycoprotein substrate	-	0.8405	84.05%
CYP3A4 substrate	+	0.5693	56.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4557	45.57%
CYP3A4 inhibition	-	0.9702	97.02%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9375	93.75%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9179	91.79%
CYP2C8 inhibition	-	0.9698	96.98%
CYP inhibitory promiscuity	-	0.9564	95.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6220	62.20%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8017	80.17%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.9041	90.41%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7848	78.48%
Acute Oral Toxicity (c)	III	0.7023	70.23%
Estrogen receptor binding	+	0.5313	53.13%
Androgen receptor binding	-	0.6449	64.49%
Thyroid receptor binding	-	0.6973	69.73%
Glucocorticoid receptor binding	-	0.7021	70.21%
Aromatase binding	-	0.4879	48.79%
PPAR gamma	-	0.6362	63.62%
Honey bee toxicity	-	0.9206	92.06%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4601	46.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	251.2 nM	Potency	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	98.12%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	96.77%	94.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	96.35%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95.16%	94.08%
CHEMBL2581	P07339	Cathepsin D	93.78%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.20%	95.56%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	91.89%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.77%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	87.36%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.36%	86.33%
CHEMBL5028	O14672	ADAM10	85.10%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.67%	97.09%
CHEMBL4208	P20618	Proteasome component C5	81.94%	90.00%
CHEMBL238	Q01959	Dopamine transporter	81.28%	95.88%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.05%	97.53%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.33%	94.97%

Plants that contains it

• Linum usitatissimum

Cross-Links

• PubChem: 5282593
• NPASS: NPC13206