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7-hydroxyhyoscyamine

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OCC(c1ccccc1)C(=O)O[C@@H]1C[C@@H]2C[C@H]([C@H](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-/m1/s1
InChIKey	WTQYWNWRJNXDEG-GKAUHRNCSA-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: 71711121

Cas: 134355-54-7

Nmrshiftdb2: 70004769

Comptox: DTXSID00856802

No compound-protein relationship available.

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): -5.24
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: -2.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.29
Plasma Protein Binding: 45.12
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: 8.91
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.18
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -2.45
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.07
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: -0.54
Rat (Acute): 2.88
Rat (Chronic Oral): 2.23
Fathead Minnow: 3.78
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: 376.26
Hydration Free Energy: -10.89
Log(D) at pH=7.4: 0.19
Log(P): 1.07
Log S: -1.78
Log(Vapor Pressure): -7.86
Melting Point: 129.47
pKa Acid: 8.07
pKa Basic: 8.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9431
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9431
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.9312
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.9312
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9206
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9206
Cyclomaltodextrin glucanotransferase	P05618	CDGT_BACS0	Bacillus sp	3	0.8989
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8989
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8989
Cyclomaltodextrin glucanotransferase	P05618	CDGT_BACS0	Bacillus sp	3	0.8989
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8926
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8926
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8879
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8879
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8877
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8877
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8740
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8740
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8711
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8711
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8680
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8680
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8678
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8678
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8413
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8413
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.8401
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.8401
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8162
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8162
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.8101
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	3	0.8101
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8038
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8038
Polyamine oxidase FMS1	P50264	FMS1_YEAST	Saccharomyces cerevisiae	3	0.7880
Polyamine oxidase FMS1	P50264	FMS1_YEAST	Saccharomyces cerevisiae	3	0.7880
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7757
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7757
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7757
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7757
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7742
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7742
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7703
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7703
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7619
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7619
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7600
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7600
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7553
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7553
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7500
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7500
Alpha-L-fucosidase, putative	Q9WYE2	Q9WYE2_THEMA	Thermotoga maritima	3	0.7487
Alpha-L-fucosidase, putative	Q9WYE2	Q9WYE2_THEMA	Thermotoga maritima	3	0.7487
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7458
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7458
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7428
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7428
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7383
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7383
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7360
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7360
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7354
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7354
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7352
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7352
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7331
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7331
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7325
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7325
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7315
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7315
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7311
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7311
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7266
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7266
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7263
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7263
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7243
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7243
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7227
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7227
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7166
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7166
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7164
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7164
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7149
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7149
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7142
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7142
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7142
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7142
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	0.7141
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	0.7141
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7127
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7127
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7110
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7110
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7094
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7094
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7089
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7089
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7088
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7088
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7074
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7074
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7063
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7063
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7061
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7061
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7020
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7020
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7018
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7018
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7008
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7008
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7006
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7006
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7004
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7004
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7003
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7003

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