2-O-acetyllycorine - Compound Card

2-O-acetyllycorine

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2-O-acetyllycorine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CC(=O)O[C@H]1C=C2CCN3[C@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3
InChI InChI=1S/C18H19NO5/c1-9(20)24-15-4-10-2-3-19-7-11-5-13-14(23-8-22-13)6-12(11)16(17(10)19)18(15)21/h4-6,15-18,21H,2-3,7-8H2,1H3/t15-,16-,17+,18+/m0/s1
InChIKey VDUHVXXNLXFPLR-WNRNVDISSA-N
Formula C18H19NO5
HBA 6
HBD 1
MW 329.35
Rotatable Bonds 1
TPSA 68.23
LogP 1.32
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 329.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crinum natans Amaryllidaceae Plantae 573721
2 Zephyranthes candida Amaryllidaceae Plantae 82257

Showing of synonyms

  • Shawky E, El Sohafy S.M, et al. (2021). Profiling of acetylcholinesterase inhibitory alkaloids from some Crinum, Habranthus and Zephyranthes species by GC–MS combined with multivariate analyses and in silico studies.. Nat Prod Res, 2021, 35(5), 807-814.. [View] [PubMed]
Pubchem: 25147570
Nmrshiftdb2: 60063439

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)C4C5C(=CCC4)CCN5C3

Level: 0

Mol. Weight: 329.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
35.74
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.27
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.9
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
-3.42
Rat (Acute)
2.58
Rat (Chronic Oral)
1.95
Fathead Minnow
3.97
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
394.88
Hydration Free Energy
-8.21
Log(D) at pH=7.4
1.62
Log(P)
1.4
Log S
-2.12
Log(Vapor Pressure)
-8.46
Melting Point
169.08
pKa Acid
8.43
pKa Basic
6.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9079
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8322
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8296
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7451
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7432
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7347
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7286
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7249
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7191
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7082
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7041
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7026
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7021

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