2-dehydroxylycorine - Compound Card

2-dehydroxylycorine

Select a section from the left sidebar

2-dehydroxylycorine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O[C@H]1CC=C2[C@H]3[C@H]1c1cc4OCOc4cc1CN3CC2
InChI InChI=1S/C16H17NO3/c18-12-2-1-9-3-4-17-7-10-5-13-14(20-8-19-13)6-11(10)15(12)16(9)17/h1,5-6,12,15-16,18H,2-4,7-8H2/t12-,15-,16-/m0/s1
InChIKey XKYSLILSDJBMCU-RCBQFDQVSA-N
Formula C16H17NO3
HBA 4
HBD 1
MW 271.32
Rotatable Bonds 0
TPSA 41.93
LogP 1.78
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 271.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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: 92276811

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 271.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
39.77
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
13.72
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.28
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.85
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
1.38
Rat (Acute)
2.41
Rat (Chronic Oral)
1.41
Fathead Minnow
3.91
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
395.09
Hydration Free Energy
-8.68
Log(D) at pH=7.4
2.04
Log(P)
1.99
Log S
-1.77
Log(Vapor Pressure)
-8.36
Melting Point
178.77
pKa Acid
10.95
pKa Basic
7.96
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 0.9046
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8868
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8543
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.8467
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8456
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8279
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8270
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7826
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7818
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7779
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7716
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7700
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7648
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7646
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7588
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7560
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7555
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7516
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7478
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7467
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7372
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7287
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7224
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7218
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7209
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7179
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7155

Download SDF