3beta-tigloyloxy-6-isovaleroyloxy-7-hydroxytropane - Compound Card

3beta-tigloyloxy-6-isovaleroyloxy-7-hydroxytropane

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3beta-tigloyloxy-6-isovaleroyloxy-7-hydroxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)O[C@@H]1CC2N(C(C1)C(C2O)OC(=O)CC(C)C)C)\C
InChI InChI=1S/C18H29NO5/c1-6-11(4)18(22)23-12-8-13-16(21)17(14(9-12)19(13)5)24-15(20)7-10(2)3/h6,10,12-14,16-17,21H,7-9H2,1-5H3/b11-6+/t12-,13?,14?,16?,17?/m1/s1
InChIKey NQACTVWQBJPZMD-QTGAIZFKSA-N
Formula C18H29NO5
HBA 6
HBD 1
MW 339.43
Rotatable Bonds 5
TPSA 76.07
LogP 1.66
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 339.2
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: 163028201
Nmrshiftdb2: 80003171

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 339.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
26.44
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
7.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.43
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
2.51
Rat (Acute)
2.33
Rat (Chronic Oral)
1.46
Fathead Minnow
4.22
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
329.38
Hydration Free Energy
-7.83
Log(D) at pH=7.4
1.36
Log(P)
2.83
Log S
-1.87
Log(Vapor Pressure)
-6.45
Melting Point
112.25
pKa Acid
7.87
pKa Basic
8.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8394
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8394
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8366
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8366
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8279
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8279
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8164
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8164
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8029
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8029
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7888
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7888
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7763
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7763
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7660
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7660
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7644
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7644
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7614
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7614
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7611
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7611
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7591
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7591
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7493
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7493
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7385
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7385
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7322
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7322
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
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 4 0.7112
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 4 0.7112
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7083
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7083
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7034
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7034
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7033
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7033

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