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3-tropoyloxy-6-acetoxytropane

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OCC(c1ccccc1)C(=O)OC1C[C@@H]2CC([C@H](C1)N2C)OC(=O)C
InChI	InChI=1S/C19H25NO5/c1-12(22)24-18-9-14-8-15(10-17(18)20(14)2)25-19(23)16(11-21)13-6-4-3-5-7-13/h3-7,14-18,21H,8-11H2,1-2H3/t14-,15?,16?,17+,18?/m1/s1
InChIKey	HMSYCWNYGYVPME-PYSDOYAXSA-N
Formula	C₁₉H₂₅NO₅
HBA	6
HBD	1
MW	347.41
Rotatable Bonds	5
TPSA	76.07
LogP	1.47
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	347.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Datura stramonium	Solanaceae	Plantae	4076

Showing of synonyms

El Bazaoui A, Bellimam MA, et al. (2011). Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS. Fitoterapia,2011,82(2),193-197. [View] [PubMed]

Pubchem: 91750092

Nmrshiftdb2: 70004783

No compound-protein relationship available.

SMILES: c1ccccc1CC(=O)OC(C2)CC(N3)CCC23

Level: 1

Mol. Weight: 347.41 g/mol

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 347.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 347.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.71
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.38

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.37
Plasma Protein Binding: 38.78
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: 11.34
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.45
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.53
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.83
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: -1.43
Rat (Acute): 2.36
Rat (Chronic Oral): 1.92
Fathead Minnow: 4.08
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: 359.54
Hydration Free Energy: -9.62
Log(D) at pH=7.4: 0.38
Log(P): 1.71
Log S: -1.79
Log(Vapor Pressure): -7.97
Melting Point: 128.55
pKa Acid: 8.33
pKa Basic: 8.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8899
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8899
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8810
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8810
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8709
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8709
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8707
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8707
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8679
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8679
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.8616
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.8616
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8419
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8419
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8407
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8407
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8391
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8391
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8303
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8303
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.8283
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.8283
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8272
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8272
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8145
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8145
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8129
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8129
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8093
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8093
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8068
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8068
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7980
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7980
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7962
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7962
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7886
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7886
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7785
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7785
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7602
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7602
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	3	0.7580
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	3	0.7580
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7550
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7550
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7540
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7540
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	0.7508
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	0.7508
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7495
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7495
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7463
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7463
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7460
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7460
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7437
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7437
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7431
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7431
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7423
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7423
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7345
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7345
Protein UshA	P07024	USHA_ECOLI	Escherichia coli	3	0.7328
Protein UshA	P07024	USHA_ECOLI	Escherichia coli	3	0.7328
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7325
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7325
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7321
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7321
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7318
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7318
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7269
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7269
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7238
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7238
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7236
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7236
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7229
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7229
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7225
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7225
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7200
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7200
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7200
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7200
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7199
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7199
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7197
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7197
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7197
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7197
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7148
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7148
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7138
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7138
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	2	0.7127
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	2	0.7127
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7126
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7126
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7124
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7124
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7111
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7111
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7098
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7098
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7090
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7090
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7084
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7084
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7070
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7070
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7057
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7057
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7048
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7048
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7040
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7040
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7031
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7031
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7019
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7019
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7014
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7014
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7008
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7008
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7006
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7006
4-alpha-glucanotransferase	O87172	MALQ_THETH	Thermus thermophilus	3	0.7000
4-alpha-glucanotransferase	O87172	MALQ_THETH	Thermus thermophilus	3	0.7000

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