Erysotrine - Compound Card

Erysotrine

Select a section from the left sidebar

Erysotrine

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc(OC)c(cc1CC3)OC
InChI InChI=1S/C19H23NO3/c1-21-15-5-4-14-7-9-20-8-6-13-10-17(22-2)18(23-3)11-16(13)19(14,20)12-15/h4-5,7,10-11,15H,6,8-9,12H2,1-3H3/t15-,19-/m0/s1
InChIKey WXVSPYOOFCCEII-KXBFYZLASA-N
Formula C19H23NO3
HBA 4
HBD 0
MW 313.4
Rotatable Bonds 3
TPSA 30.93
LogP 2.67
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 313.17
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: 442219
Kegg Ligand: C09423
Chebi: 4838
Nmrshiftdb2: 60024892
Metabolights: MTBLC4838
Bindingdb: 50006648

No compound-protein relationship available.

Structure

SMILES: C1CC=CC(C123)=CCN3CCc4c2cccc4

Level: 0

Mol. Weight: 223.32 g/mol

Anti-hiv
Cytotoxicity

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.510
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.650
Plasma Protein Binding
37.75
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
3.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.660
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
9.430
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
-4.210
Rat (Acute)
3.150
Rat (Chronic Oral)
1.610
Fathead Minnow
4.290
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
364.830
Hydration Free Energy
-6.920
Log(D) at pH=7.4
2.050
Log(P)
2.47
Log S
-1.33
Log(Vapor Pressure)
-5.91
Melting Point
138.66
pKa Acid
11.78
pKa Basic
8.1
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 0.9806
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9806
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.9285
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.9285
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9131
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9131
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9104
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9104
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8935
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8935
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8831
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8831
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8563
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8563
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8490
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8490
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8463
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8463
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8432
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8432
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8346
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8346
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8335
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8335
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8045
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8045
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8030
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8030
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7992
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7992
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7816
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7816
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7752
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7752
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7724
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7724
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7717
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7717
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7693
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7693
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7668
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7668
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7627
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7627
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7625
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7625
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7590
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7590
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7540
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7540
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7532
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7532
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7528
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7528
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7528
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7528
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7495
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7495
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7460
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7460
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7453
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7453
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7429
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7429
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7424
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7424
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7416
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7416
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7409
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7409
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7400
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7400
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7348
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7348
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7348
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7348
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7340
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7340
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7331
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7331
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7315
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7315
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7291
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7291
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7290
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7290
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7287
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7287
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 3 0.7282
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 3 0.7282
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7264
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7264
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7252
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7252
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7228
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7228
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7222
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7222
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7201
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7201
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7191
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7191
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7182
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7182
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7175
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7175
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7162
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7162
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7151
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7151
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7147
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7147
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7133
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7133
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7131
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7131
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7096
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7096
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7086
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7086
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7072
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7072
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7070
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7070
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7067
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7067
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7029
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7029
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7025
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7025
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7021
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7021
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7017
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7017
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7004
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7004

Download SDF