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3-tigloyloxy-6-isobutyryloxy-7-hydroxytropane

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	C/C=C(/C(=O)OC1CC2C(C(C(C1)N2C)O)OC(=O)C(C)C)\C
InChI	InChI=1S/C17H27NO5/c1-6-10(4)17(21)22-11-7-12-14(19)15(13(8-11)18(12)5)23-16(20)9(2)3/h6,9,11-15,19H,7-8H2,1-5H3/b10-6+
InChIKey	RZKWUOOSGIFSGP-UXBLZVDNSA-N
Formula	C₁₇H₂₇NO₅
HBA	6
HBD	1
MW	325.41
Rotatable Bonds	4
TPSA	76.07
LogP	1.27
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.76
Exact Mass	325.19
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: 91700487

Nmrshiftdb2: 70004802

No compound-protein relationship available.

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 325.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.8
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.71
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.35
Plasma Protein Binding: 15.79
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: 6.09
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.03
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.46
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.37
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: 3.63
Rat (Acute): 2.33
Rat (Chronic Oral): 1.46
Fathead Minnow: 4.27
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: 321.08
Hydration Free Energy: -8.45
Log(D) at pH=7.4: 0.82
Log(P): 2.39
Log S: -1.55
Log(Vapor Pressure): -6.34
Melting Point: 113.37
pKa Acid: 7.94
pKa Basic: 8.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8303
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8303
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8204
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8204
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8105
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8105
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7961
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7961
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7925
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7925
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7872
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7872
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7672
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7672
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7597
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7590
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7590
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7484
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7484
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7414
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7414
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7395
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7395
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7379
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7379
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7215
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7215
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7208
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7208
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7127
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7127
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7102
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7102
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7075
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7075
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7042
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7042

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