9-angeloylretronecine - Compound Card

9-angeloylretronecine

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9-angeloylretronecine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(\C(=O)OCC1=CCN2(=O)[C@H]1[C@H](O)CC2)/C
InChI InChI=1S/C13H19NO4/c1-3-9(2)13(16)18-8-10-4-6-14(17)7-5-11(15)12(10)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3-/t11-,12-,14?/m1/s1
InChIKey HHIPTBVXCKBSAM-ZSXZLUMUSA-N
Formula C13H19NO4
HBA 4
HBD 1
MW 253.3
Rotatable Bonds 3
TPSA 69.59
LogP 0.88
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 253.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crotalaria pycnostachya Leguminosae/Fabaceae Plantae 1670847

Showing of synonyms

  • Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem: 6442556

No compound-protein relationship available.

Structure

SMILES: C1C=CC(N12=O)CCC2

Level: 0

Mol. Weight: 253.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.17
Plasma Protein Binding
34.56
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
4.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.05
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.35
Micronucleos
Safe
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
-1.4
Rat (Acute)
2.67
Rat (Chronic Oral)
1.77
Fathead Minnow
3.92
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
297.42
Hydration Free Energy
-9.61
Log(D) at pH=7.4
0.71
Log(P)
-0.46
Log S
-0.51
Log(Vapor Pressure)
-6.16
Melting Point
118.8
pKa Acid
5.98
pKa Basic
0.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.9373
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.9373
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8654
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8654
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8436
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8436
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8356
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8356
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8332
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8332
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8222
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8222
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8060
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8006
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8006
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7720
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7720
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7665
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7665
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7652
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7652
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7571
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7571
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7556
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7556
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7551
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7551
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7546
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7546
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7545
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7524
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7524
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7486
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7486
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7454
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7454
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7423
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7423
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7377
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7377
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7313
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7313
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7231
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7231
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7217
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7217
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7208
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7208
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7191
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7191
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7185
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7185
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7140
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7140
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7128
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7128
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7086
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7086
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7057
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7057
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7054
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7054
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7043
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7043
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7042
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7042
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7041
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7041
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7038
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7038
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7010
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7010
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 3 0.7004
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 3 0.7004

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