7-(2-methylbutyryl)-retronecine - Compound Card

7-(2-methylbutyryl)-retronecine

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7-(2-methylbutyryl)-retronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(C(=O)O[C@@H]1CCN2C1C(=CC2)CO)C
InChI InChI=1S/C13H21NO3/c1-3-9(2)13(16)17-11-5-7-14-6-4-10(8-15)12(11)14/h4,9,11-12,15H,3,5-8H2,1-2H3/t9?,11-,12?/m1/s1
InChIKey NSBSOFPYQQNEGC-CKBZRRDASA-N
Formula C13H21NO3
HBA 4
HBD 1
MW 239.31
Rotatable Bonds 4
TPSA 49.77
LogP 0.95
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 239.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Echium humile Boraginaceae Plantae 161689

Showing of synonyms

  • El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile. Phytochemistry,1996,42(1),225-230. [View]
Pubchem: 6431049

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 239.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.17
Plasma Protein Binding
19.32
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
7.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.27
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.47
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
0.43
Rat (Acute)
3.13
Rat (Chronic Oral)
1.7
Fathead Minnow
3.7
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
293.96
Hydration Free Energy
-9.34
Log(D) at pH=7.4
0.18
Log(P)
1.2
Log S
-0.9
Log(Vapor Pressure)
-4.98
Melting Point
84.4
pKa Acid
8.81
pKa Basic
8.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9377
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9377
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8411
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8411
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8063
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7927
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7927
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7877
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7877
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7856
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7856
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7707
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7707
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7588
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7588
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7460
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7460
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7451
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7451
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7338
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7338
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7248
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7248
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7141
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7141
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7075
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7075
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7071
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7071

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