Homolycorine - Compound Card

Homolycorine

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Homolycorine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles COc1cc2[C@@H]3[C@@H](CC=C4[C@H]3N(C)CC4)OC(=O)c2cc1OC
InChI InChI=1S/C18H21NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-17H,5-7H2,1-3H3/t13-,16-,17-/m1/s1
InChIKey WXZAKVLYZHWSNF-KBRIMQKVSA-N
Formula C18H21NO4
HBA 5
HBD 0
MW 315.37
Rotatable Bonds 2
TPSA 48.0
LogP 2.36
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 315.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Narcissus species Amaryllidaceae Plantae 54843
2 Zephyranthes candida Amaryllidaceae Plantae 82257

Showing of synonyms

  • Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
  • 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: 160473
Nmrshiftdb2: 60066530

No compound-protein relationship available.

Structure

SMILES: C1CNC(C1=2)C3c4c(cccc4)C(=O)OC3CC2

Level: 0

Mol. Weight: 315.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
35.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.960
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.320
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.150
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
-2.390
Rat (Acute)
3.280
Rat (Chronic Oral)
1.530
Fathead Minnow
4.090
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
371.320
Hydration Free Energy
-8.040
Log(D) at pH=7.4
2.030
Log(P)
1.97
Log S
-1.93
Log(Vapor Pressure)
-7.08
Melting Point
147.71
pKa Acid
8.15
pKa Basic
7.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9446
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9446
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8807
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8807
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7887
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7887
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7878
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7878
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7850
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7850
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7722
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7722
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7678
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7678
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7649
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7649
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7587
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7587
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7533
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7533
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7518
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7518
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7474
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7474
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7445
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7445
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7440
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7440
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7435
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7435
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7395
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7395
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7364
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7364
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7332
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7332
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7329
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7329
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7263
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7263
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7201
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7201
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7200
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7200
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7162
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7162
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7066
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7066
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7022
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7022
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7019
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7019

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