Erysodine - Compound Card

Erysodine

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Erysodine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc(OC)c(cc1CC3)O
InChI InChI=1S/C18H21NO3/c1-21-14-4-3-13-6-8-19-7-5-12-9-16(20)17(22-2)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1
InChIKey BDIVMECULLJBMU-KSSFIOAISA-N
Formula C18H21NO3
HBA 4
HBD 1
MW 299.37
Rotatable Bonds 2
TPSA 41.93
LogP 2.37
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 299.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573

Showing of synonyms

  • Mohammed MM, Ibrahim NA, et al. (2012). Anti-HIV-1 and cytotoxicity of the alkaloids of Erythrina abyssinica Lam. growing in Sudan. Natural Product Research,2012,26(17),1565-1575. [View] [PubMed]
Pubchem: 169017
Chebi: 192381
Nmrshiftdb2: 60024897
Metabolights: MTBLC192381
Bindingdb: 50006647
CPRiL: 240536
Structure

SMILES: C1CC=CC(C123)=CCN3CCc4c2cccc4

Level: 0

Mol. Weight: 299.37 g/mol

Anti-hiv
Cytotoxicity

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.470
Plasma Protein Binding
37.38
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
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
9.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.370
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.010
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
9.020
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
-3.310
Rat (Acute)
2.940
Rat (Chronic Oral)
1.830
Fathead Minnow
4.060
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
359.680
Hydration Free Energy
-7.890
Log(D) at pH=7.4
1.990
Log(P)
2.01
Log S
-1.56
Log(Vapor Pressure)
-6.24
Melting Point
182.07
pKa Acid
9.98
pKa Basic
7.6
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 0.9613
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9613
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9110
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9110
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8911
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8911
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8899
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8899
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8853
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8853
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8780
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8780
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8761
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8761
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8746
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8746
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8608
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8608
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 3 0.8457
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 3 0.8457
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8423
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8423
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8372
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8372
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8354
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8354
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8344
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8312
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8312
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8288
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8288
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8218
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8218
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8204
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8204
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8185
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8185
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8173
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8173
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8144
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8144
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8123
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8123
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8122
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8071
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8059
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8059
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8026
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8026
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7968
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7968
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7965
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7965
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7916
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7916
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7890
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7890
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7795
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7795
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7782
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7782
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7740
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7740
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7702
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7702
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7692
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7692
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7669
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7669
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7634
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7634
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7624
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7624
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7534
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7534
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7511
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7511
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7438
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7438
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7424
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7396
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7396
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7376
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7376
Petrobactin biosynthesis protein AsbB Q81RQ8 Q81RQ8_BACAN Bacillus anthracis 3 0.7352
Petrobactin biosynthesis protein AsbB Q81RQ8 Q81RQ8_BACAN Bacillus anthracis 3 0.7352
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7307
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7307
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7307
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7307
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7286
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7286
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7279
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7279
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7274
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7274
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7262
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7262
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7261
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7261
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7260
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7260
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7251
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7251
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7244
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7244
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 3 0.7241
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 3 0.7241
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7234
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7234
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7203
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7178
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7178
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7178
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7178
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7176
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7176
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7176
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7176
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7168
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7168
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7161
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7161
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7146
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7146
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7142
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7142
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7103
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7103
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7093
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7093
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7087
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7087
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7082
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7082
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7075
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7075
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7072
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7072
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7062
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7062
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7051
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7051
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7036
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7036
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7016
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7016
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7014
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7014
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7010
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7010
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7008
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7008
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7001
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7001

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