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3-tropoyloxy-6-isobutyryloxytropane

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OCC(c1ccccc1)C(=O)OC1CC2CC(C(C1)N2C)OC(=O)C(C)C
InChI	InChI=1S/C21H29NO5/c1-13(2)20(24)27-19-10-15-9-16(11-18(19)22(15)3)26-21(25)17(12-23)14-7-5-4-6-8-14/h4-8,13,15-19,23H,9-12H2,1-3H3
InChIKey	GVILSBKQFFAYSA-UHFFFAOYSA-N
Formula	C₂₁H₂₉NO₅
HBA	6
HBD	1
MW	375.47
Rotatable Bonds	6
TPSA	76.07
LogP	2.11
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	375.2
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: 123909342

Nmrshiftdb2: 70004761

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 375.47 g/mol

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 375.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 375.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.72
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.5
Plasma Protein Binding: 20.64
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: 12.31
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.76
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.08
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.85
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: -3.24
Rat (Acute): 2.52
Rat (Chronic Oral): 1.86
Fathead Minnow: 4.14
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: 365.11
Hydration Free Energy: -7.5
Log(D) at pH=7.4: 1.29
Log(P): 2.65
Log S: -2.1
Log(Vapor Pressure): -8.18
Melting Point: 116.58
pKa Acid: 8.33
pKa Basic: 8.98

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	0.9336
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.9336
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.9112
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.9112
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8692
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8692
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8617
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8617
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8318
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8318
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8285
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8285
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8256
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8256
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8242
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8242
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	3	0.8107
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	3	0.8107
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8009
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8009
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7969
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7969
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7941
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7941
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7861
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7861
Indole-3-glycerol phosphate synthase	P9WFX7	TRPC_MYCTU	Mycobacterium tuberculosis	3	0.7856
Indole-3-glycerol phosphate synthase	P9WFX7	TRPC_MYCTU	Mycobacterium tuberculosis	3	0.7856
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7721
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7721
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.7687
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.7687
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7681
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7681
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7629
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7629
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7608
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7608
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7536
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7536
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7522
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7522
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7513
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7513
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7510
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7510
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7499
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7499
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7493
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7493
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7483
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7483
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7472
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7472
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7356
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7356
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7313
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7313
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7293
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7293
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	0.7287
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	0.7287
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7248
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7248
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7215
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7215
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7207
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7207
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7194
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7194
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7192
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7192
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7181
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7181
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7165
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7165
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7161
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7161
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7158
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7158
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7136
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7136
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7117
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7117
Ferric enterobactin-binding periplasmic protein FepB	P0AEL6	FEPB_ECOLI	Escherichia coli	3	0.7109
Ferric enterobactin-binding periplasmic protein FepB	P0AEL6	FEPB_ECOLI	Escherichia coli	3	0.7109
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7099
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7099
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7092
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7092
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7070
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7070
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7061
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7061
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7060
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7060
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7049
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7049
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7040
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	2	0.7040
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7014
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7014
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7008
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7008
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7004
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7004
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7004
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7004

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