3-tigloyloxy-6-propionyloxy-7-hydroxytropane - Compound Card

3-tigloyloxy-6-propionyloxy-7-hydroxytropane

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3-tigloyloxy-6-propionyloxy-7-hydroxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(=O)OC1C2CC(CC(C1O)N2C)OC(=O)/C(=C/C)/C
InChI InChI=1S/C16H25NO5/c1-5-9(3)16(20)21-10-7-11-14(19)15(22-13(18)6-2)12(8-10)17(11)4/h5,10-12,14-15,19H,6-8H2,1-4H3/b9-5+
InChIKey HGOLJZZEGFBRMR-WEVVVXLNSA-N
Formula C16H25NO5
HBA 6
HBD 1
MW 311.38
Rotatable Bonds 4
TPSA 76.07
LogP 1.02
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 311.17
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: 91700480
Nmrshiftdb2: 70004789

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 311.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.28
Plasma Protein Binding
13.16
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
5.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.17
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.5
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.31
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
4.0
Rat (Acute)
2.14
Rat (Chronic Oral)
1.45
Fathead Minnow
4.16
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
321.42
Hydration Free Energy
-9.21
Log(D) at pH=7.4
0.44
Log(P)
1.94
Log S
-1.41
Log(Vapor Pressure)
-6.29
Melting Point
102.32
pKa Acid
8.15
pKa Basic
7.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8982
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8982
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8426
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8426
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8324
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8324
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8252
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8252
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8180
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8180
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8124
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8124
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8016
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8016
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7982
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7982
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7949
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7949
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7846
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7846
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7784
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7784
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7706
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7706
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7610
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7610
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7566
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7566
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7550
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7550
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7540
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7540
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7466
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7466
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7458
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7458
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7432
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7432
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7406
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7406
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7403
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7367
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7367
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7364
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7351
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7351
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7296
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7296
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7179
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7179
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7166
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7166
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7160
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7160
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7153
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7153
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7124
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7124
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7034
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7034
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7015
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7015
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7014
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7014

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