7-tigloyl-9-(2,3-dihydroxy propanoyl) retronecine - Compound Card

7-tigloyl-9-(2,3-dihydroxy propanoyl) retronecine

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7-tigloyl-9-(2,3-dihydroxy propanoyl) retronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles OCC(C(=O)OC[C@H]1CCN2C1[C@@H](CC2)OC(=O)/C(=C/C)/C)O
InChI InChI=1S/C16H25NO6/c1-3-10(2)15(20)23-13-5-7-17-6-4-11(14(13)17)9-22-16(21)12(19)8-18/h3,11-14,18-19H,4-9H2,1-2H3/b10-3+/t11-,12?,13-,14?/m1/s1
InChIKey UCZOPSUTRUWZNY-YRFYIIOPSA-N
Formula C16H25NO6
HBA 7
HBD 2
MW 327.38
Rotatable Bonds 6
TPSA 96.3
LogP -0.14
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 327.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alkanna orientalis Boraginaceae Plantae 543563

Showing of synonyms

  • El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]
Pubchem: 6429062
Nmrshiftdb2: 60077942

No compound-protein relationship available.

Structure

SMILES: C1CCN(C12)CCC2

Level: 0

Mol. Weight: 327.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.350
Plasma Protein Binding
30.69
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.020
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.040
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
-1.760
Rat (Acute)
2.060
Rat (Chronic Oral)
2.130
Fathead Minnow
3.990
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
374.160
Hydration Free Energy
-12.110
Log(D) at pH=7.4
0.290
Log(P)
0.48
Log S
-1.18
Log(Vapor Pressure)
-7.93
Melting Point
117.33
pKa Acid
7.61
pKa Basic
7.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8948
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8948
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8733
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8733
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8572
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8572
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8556
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8556
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.8416
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.8416
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8313
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8313
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8148
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8148
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7843
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7843
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7702
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7702
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7323
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7323
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7262
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7262
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7249
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7249
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7125
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7125
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7118
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7118
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7114
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7114
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7075
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7075

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