9-tigloylretronecine - Compound Card

9-tigloylretronecine

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9-tigloylretronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C(/C(=O)OCC1=CCN2[C@H]1[C@H](O)CC2)\C
InChI InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-8-10-4-6-14-7-5-11(15)12(10)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3+/t11-,12-/m1/s1
InChIKey VYUQPLFRNDQDHW-UHTQEIBISA-N
Formula C13H19NO3
HBA 4
HBD 1
MW 237.3
Rotatable Bonds 3
TPSA 49.77
LogP 0.87
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 237.14
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: 14313398
Nmrshiftdb2: 60077944

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 237.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.25
Plasma Protein Binding
24.28
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.33
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.65
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
0.35
Rat (Acute)
3.73
Rat (Chronic Oral)
1.69
Fathead Minnow
4.0
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
306.58
Hydration Free Energy
-10.01
Log(D) at pH=7.4
0.81
Log(P)
1.24
Log S
-0.88
Log(Vapor Pressure)
-5.56
Melting Point
106.89
pKa Acid
8.53
pKa Basic
7.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9374
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9374
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9184
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9184
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9017
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9017
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8880
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8880
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8626
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8626
Cyclomaltodextrin glucanotransferase P05618 CDGT_BACS0 Bacillus sp 3 0.7925
Cyclomaltodextrin glucanotransferase P05618 CDGT_BACS0 Bacillus sp 3 0.7925
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7890
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7890
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7368
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7368
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7312
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7312
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7273
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7273
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7258
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7258
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7181
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7181
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7138
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7138
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7105
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7105
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7097
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7097
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7054
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7054
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7024
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7024

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