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6-hydroxyhyoscyamine

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OC[C@@H](c1ccccc1)C(=O)O[C@H]1CC2C[C@@H](C(C1)N2C)O
InChI	InChI=1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12?,13-,14-,15?,16-/m0/s1
InChIKey	WTQYWNWRJNXDEG-ABSNHQIMSA-N
Formula	C₁₇H₂₃NO₄
HBA	5
HBD	2
MW	305.37
Rotatable Bonds	4
TPSA	70.0
LogP	0.9
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.59
Exact Mass	305.16
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: 442993

Cas: 55869-99-3

Kegg Ligand: C10842

Chebi: 2735

CPRiL: 29043

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

Level: 1

Mol. Weight: 305.37 g/mol

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 305.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 305.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.25
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.58
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.29
Plasma Protein Binding: 39.33
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: 8.88
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -2.47
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.02
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: -1.52
Rat (Acute): 2.87
Rat (Chronic Oral): 2.26
Fathead Minnow: 3.79
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: 377.12
Hydration Free Energy: -11.0
Log(D) at pH=7.4: 0.16
Log(P): 1.05
Log S: -1.77
Log(Vapor Pressure): -7.83
Melting Point: 125.67
pKa Acid: 8.08
pKa Basic: 8.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9476
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9476
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9275
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9275
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9155
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9155
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9135
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9135
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8840
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8840
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8803
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8803
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8795
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8795
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8769
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8769
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.8752
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.8752
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8743
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8743
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8674
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8674
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8647
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8647
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8540
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8540
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8461
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8461
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8340
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8340
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8314
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8314
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	3	0.8286
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	3	0.8286
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8216
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8216
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8204
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8204
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8174
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8174
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.8095
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.8095
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8030
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8030
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8001
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8001
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7992
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7992
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7959
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7959
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7952
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7952
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7805
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7805
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.7737
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.7737
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7596
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7596
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7557
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7557
Indole-3-glycerol phosphate synthase	P9WFX7	TRPC_MYCTU	Mycobacterium tuberculosis	2	0.7540
Indole-3-glycerol phosphate synthase	P9WFX7	TRPC_MYCTU	Mycobacterium tuberculosis	2	0.7540
Cobalt-precorrin-4 C(11)-methyltransferase	O87696	CBIF_BACME	Priestia megaterium	3	0.7527
Cobalt-precorrin-4 C(11)-methyltransferase	O87696	CBIF_BACME	Priestia megaterium	3	0.7527
Glycogenin-1	P46976	GLYG_HUMAN	Homo sapiens	3	0.7514
Glycogenin-1	P46976	GLYG_HUMAN	Homo sapiens	3	0.7514
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7507
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7507
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7448
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7448
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7419
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7419
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7397
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7397
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7393
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7393
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7371
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7371
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7369
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7369
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7339
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7339
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7269
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7269
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7263
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7263
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7261
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7261
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7257
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7257
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7253
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7253
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7248
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7248
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7241
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7241
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7231
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7231
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7215
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7215
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7202
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7202
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7200
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7200
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7199
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7199
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7182
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7182
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7177
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7177
Uridine phosphorylase	Q5SID9	Q5SID9_THET8	Thermus thermophilus	3	0.7168
Uridine phosphorylase	Q5SID9	Q5SID9_THET8	Thermus thermophilus	3	0.7168
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	0.7138
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	0.7138
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7134
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7134
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7124
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7124
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7119
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7119
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7094
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7094
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	3	0.7090
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	3	0.7090
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7085
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7085
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7049
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7049
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7046
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7046
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7036
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7036
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7025
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7025
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7004
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7004

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