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6-hydroxyapoatropine

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OC1CC2N(C1CC(C2)OC(=O)C(=C)c1ccccc1)C
InChI	InChI=1S/C17H21NO3/c1-11(12-6-4-3-5-7-12)17(20)21-14-8-13-9-16(19)15(10-14)18(13)2/h3-7,13-16,19H,1,8-10H2,2H3
InChIKey	IZVZMPYXRCTCEG-UHFFFAOYSA-N
Formula	C₁₇H₂₁NO₃
HBA	4
HBD	1
MW	287.36
Rotatable Bonds	3
TPSA	49.77
LogP	1.84
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	287.15
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: 91700478

Cas: 109496-01-7

Nmrshiftdb2: 70004778

No compound-protein relationship available.

SMILES: c1ccccc1C(=C)C(=O)OC(C2)CC(N3)CCC23

Level: 1

Mol. Weight: 287.36 g/mol

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 287.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 287.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.85
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.520
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.51

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.420
Plasma Protein Binding: 24.47
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: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.930
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.470
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.730
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.200
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: 4.260
Rat (Acute): 2.550
Rat (Chronic Oral): 1.730
Fathead Minnow: 4.010
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: 330.640
Hydration Free Energy: -9.240
Log(D) at pH=7.4: 1.200
Log(P): 2.31
Log S: -2.09
Log(Vapor Pressure): -6.69
Melting Point: 123.98
pKa Acid: 7.12
pKa Basic: 8.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9314
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9314
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9299
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9299
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9044
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9044
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9010
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9010
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8564
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8564
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8320
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8320
Putative FAD-dependent oxygenase EncM	Q9KHK2	Q9KHK2_9ACTN	Streptomyces maritimus	3	0.8247
Putative FAD-dependent oxygenase EncM	Q9KHK2	Q9KHK2_9ACTN	Streptomyces maritimus	3	0.8247
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8155
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8155
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8111
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8111
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7838
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7838
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7650
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7650
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7638
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7638
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7532
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7532
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	2	0.7455
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	2	0.7455
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7414
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7414
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7413
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7413
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7400
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7400
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7379
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7379
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7369
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7369
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7360
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7360
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7344
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7344
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7318
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7318
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7296
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	3	0.7296
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7286
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7286
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7266
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7266
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7254
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7254
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7236
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7236
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7223
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7223
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7208
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7208
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7202
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7202
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7193
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7193
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7190
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7190
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7185
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7185
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7180
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7180
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7180
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7180
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7173
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7173
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7172
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7172
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7162
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7162
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7159
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7159
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7155
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7155
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7150
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7150
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7149
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7149
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7129
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7129
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7129
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7129
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7124
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7124
Heat shock 70 kDa protein 1A	P0DMV8	HS71A_HUMAN	Homo sapiens	3	0.7101
Heat shock 70 kDa protein 1A	P0DMV8	HS71A_HUMAN	Homo sapiens	3	0.7101
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7098
Carbonic anhydrase	Q39588	Q39588_CHLRE	Chlamydomonas reinhardtii	2	0.7098
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7089
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7089
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7084
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7084
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7083
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7083
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7076
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7076
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	2	0.7067
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	2	0.7067
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7054
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7054
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7047
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7047
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7047
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7047
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7045
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7045
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7045
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7045
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7036
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7036
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7036
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7036
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7032
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7032
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7027
Proline--tRNA ligase	Q8I5R7	SYP_PLAF7	Plasmodium falciparum	3	0.7027
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7015
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7015
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7002
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7002

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