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Atropine
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Tropane Alkaloid
| Canonical Smiles | OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)N2C |
|---|---|
| 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 |
| InChIKey | RKUNBYITZUJHSG-UHFFFAOYSA-N |
| Formula | C17H23NO3 |
| HBA | 4 |
| HBD | 1 |
| MW | 289.38 |
| Rotatable Bonds | 4 |
| TPSA | 49.77 |
| LogP | 1.93 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 289.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hyoscyamus muticus | Solanaceae | Plantae | 35626 |
Showing of synonyms
Atropine
Daturine (sulfate)
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
83454-31-3
Benzeneacetic acid, .alpha.-(hydroxymethyl)- 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester endo-(.+/-.)-
L-Hyoscyamine (sulfate)
CHEMBL195
SR-01000075162
Benzeneacetic acid, .alpha.-(hydroxymethyl)-, 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [3(S)-endo]-
Atropine,(-)
Atropisol (Salt/Mix)
Spectrum_001159
L-HYOSCYAMINE HEMISULFATE SALT
()-HYOSCYAMINE
(.+/-.)-Atropine
Prestwick0_000565
Prestwick1_000565
Prestwick2_000565
Prestwick3_000565
Spectrum2_000094
Spectrum3_000307
Spectrum4_001813
Spectrum5_000545
(.+/-.)-Hyoscyamine
UPCMLD-DP018
SCHEMBL2813
(.+/-.)-Tropyl tropate
CHEMBL9751
Lopac0_000042
Lopac0_000567
Oprea1_442738
BSPBio_000350
BSPBio_001874
KBioGR_002450
KBioSS_001639
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
NAA26935
NSC_3661
Tox21_500567
BBL033747
STL374102
(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate
AKOS009031432
CCG-204138
FA31540
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
NCGC00015026-28
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
DB-051989
A0754
AB00514677
CS-0526746
EU-0100567
H0450
NS00008542
D88314
H 9002
SBI-0050031.0001
AB00514677_07
2-Phenylhydracrylic acid 3-.alpha.-tropanyl ester
L001264
.beta.-Phenyl-.gamma.-oxypropionsaeure-tropyl-ester
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropate #
SR-01000075162-1
SR-01000075162-2
BRD-A93739713-065-03-5
BRD-A93739713-065-04-3
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
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-
Benzeneacetic acid, .alpha.-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester
Pubchem:
3661
Cas:
83454-31-3
Gnps:
CCMSLIB00006396832
Chebi:
104243
Nmrshiftdb2:
10008977
Metabolights:
MTBLC104243
Chembl:
CHEMBL9751
Bindingdb:
86231
CPRiL:
579
SMILES: c1ccccc1CC(=O)OC(C2)CC(N3)CCC23
Level: 1
Mol. Weight: 289.38 g/mol
SMILES: C12CCC(N2)CCC1
Level: 0
Mol. Weight: 289.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 289.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.02
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.48
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.27
- Plasma Protein Binding
- 24.48
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.2
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.07
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -2.98
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.42
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.46
- Rat (Acute)
- 2.83
- Rat (Chronic Oral)
- 2.05
- Fathead Minnow
- 3.98
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 351.1
- Hydration Free Energy
- -9.35
- Log(D) at pH=7.4
- 0.87
- Log(P)
- 1.83
- Log S
- -1.8
- Log(Vapor Pressure)
- -6.46
- Melting Point
- 113.72
- pKa Acid
- 9.5
- pKa Basic
- 9.35
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9477 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.9126 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9049 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8962 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8877 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8769 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8713 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8688 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8351 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8324 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8246 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 3 | 0.8236 |
| Polyamine oxidase FMS1 | P50264 | FMS1_YEAST | Saccharomyces cerevisiae | 3 | 0.8167 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8161 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8135 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8095 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 3 | 0.8050 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.8049 |
| Indole-3-glycerol phosphate synthase | P9WFX7 | TRPC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7999 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7990 |
| 4-alpha-glucanotransferase | O87172 | MALQ_THETH | Thermus thermophilus | 3 | 0.7936 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7760 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7620 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7579 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7535 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7481 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7457 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7437 |
| 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase | O33877 | FABA_PSEAE | Pseudomonas aeruginosa | 3 | 0.7419 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7393 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7381 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7358 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7345 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 3 | 0.7334 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7329 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7325 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic | Q1XH05 | HGL1B_WHEAT | Triticum aestivum | 3 | 0.7325 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 2 | 0.7325 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7307 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7307 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7306 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7296 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7295 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic | P49235 | HGGL1_MAIZE | Zea mays | 2 | 0.7293 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7287 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7263 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7240 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7238 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7234 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7229 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7219 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7212 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7207 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7191 |
| Archaeal actin homolog | Q9HKL4 | ACTH_THEAC | Thermoplasma acidophilum | 2 | 0.7190 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7184 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7177 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 4 | 0.7173 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7172 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 2 | 0.7151 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7146 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7141 |
| Karilysin | D0EM77 | KLY_TANFA | Tannerella forsythia | 3 | 0.7135 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7115 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7102 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 2 | 0.7079 |
| Endoglycoceramidase II | O33853 | O33853_RHOSO | Rhodococcus sp | 3 | 0.7072 |
| Type II methyltransferase M1.MboII | P23192 | MTM2_MORBO | Moraxella bovis | 3 | 0.7068 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7053 |
| cAMP-dependent protein kinase catalytic subunit alpha | P05132 | KAPCA_MOUSE | Mus musculus | 3 | 0.7046 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7035 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7021 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7019 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7017 |
| Alanine racemase | Q180W0 | Q180W0_CLOD6 | Clostridioides difficile | 2 | 0.7009 |