Lycorine - Compound Card

Lycorine

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Lycorine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles O[C@H]1C=C2CCN3[C@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3
InChI InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
InChIKey XGVJWXAYKUHDOO-DANNLKNASA-N
Formula C16H17NO4
HBA 5
HBD 2
MW 287.32
Rotatable Bonds 0
TPSA 62.16
LogP 0.75
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 287.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lycoris sanguinea Amaryllidaceae Plantae 108053
2 Crinum augustum Amaryllidaceae Plantae 16055
3 Narcissus tazetta Amaryllidaceae Plantae 54860
4 Haemanthus multiflorus Amaryllidaceae Plantae 82246
5 Clivia miniata Amaryllidaceae Plantae 16049
6 Clivia nobilis Amaryllidaceae Plantae 112537
7 Crinum americanum Amaryllidaceae Plantae 164437
8 Narcissus species Amaryllidaceae Plantae 54843

Showing of synonyms

  • Abdallah OM, Ali AA and Itokawa H. (1989). 2-O-acetyl chlidanthine; an alkaloid from Haemanthus multiflorus. Phytochemistry,1989,28(11),3248-3249. [View]
  • Ali AA, Ross SA, et al. (1983). Clivonidine, a new alkaloid from Clivia miniata. Journal of Natural Products,1983,46(3),350-352. [View]
  • 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]
  • Abdallah OM. (1995). Minor alkaloids from Lycoris sanguinea. Phytochemistry,1995,39(2),477-478. [View]
  • Abdallah OM. (1993). Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry,1993,34(5),1447-1448. [View]
  • Jeffs PW, Mueller L, et al. (1988). Nobilisine, a new alkaloid from Clivia nobilis. Journal of Natural Products,1988,51(3),549-554. [View]
  • Ali AA, El Sayed HM, et al. (1986). Oxocrinine and other alkaloids from Crinum americanum. Phytochemistry,1986,25(10),2399-2401. [View]
  • Ali AA, Kating H, et al. (1981). Two non-hydroxylated alkaloids in Crinum augustum. Phytochemistry,1981,20(5),1121-1123. [View]
Pubchem: 72378
Kegg Ligand: C08532
Chebi: 6601
Nmrshiftdb2: 60025519
Metabolights: MTBLC6601
Pdb Ligand: 3KD
Bindingdb: 50221066
CPRiL: 56203
Structure

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

Level: 0

Mol. Weight: 287.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
32.05
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
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
9.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.16
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
-1.37
Rat (Acute)
2.91
Rat (Chronic Oral)
1.56
Fathead Minnow
3.99
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
399.33
Hydration Free Energy
-9.53
Log(D) at pH=7.4
1.28
Log(P)
0.33
Log S
-1.2
Log(Vapor Pressure)
-9.65
Melting Point
216.21
pKa Acid
10.0
pKa Basic
6.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8465
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8465
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8321
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8321
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7934
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7934
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7861
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7861
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7523
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7523
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7446
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7446
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7340
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7340
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7323
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7323
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7306
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7306
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7289
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7289
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7287
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7287
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7263
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7263
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7239
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7239
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7170
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7170
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7155
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7155
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7145
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7145
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7141
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7141
GMP reductase 2 Q9P2T1 GMPR2_HUMAN Homo sapiens 3 0.7087
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7087
GMP reductase 2 Q9P2T1 GMPR2_HUMAN Homo sapiens 3 0.7087
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7087
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7084
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7084
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7024
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7024
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7014
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7014

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