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Erythraline

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc2OCOc2cc1CC3
InChI	InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3/t14-,18-/m0/s1
InChIKey	TVOFUERNMZTYRM-KSSFIOAISA-N
Formula	C₁₈H₁₉NO₃
HBA	4
HBD	0
MW	297.35
Rotatable Bonds	1
TPSA	30.93
LogP	2.38
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	297.14
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: 5317205

Cas: 466-77-3

Gnps: CCMSLIB00000081229

Chebi: 196318

Nmrshiftdb2: 60024898

Chembl: CHEMBL518262

CPRiL: 226554

SMILES: C1CC=CC(C123)=CCN3CCc4c2cc5c(c4)OCO5

Level: 0

Mol. Weight: 297.35 g/mol

Anti-hiv

Cytotoxicity

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.480
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 45.15
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.260
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.060
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.070
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.650
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: Toxic
T. Pyriformis: -1.860
Rat (Acute): 2.750
Rat (Chronic Oral): 1.300
Fathead Minnow: 4.180
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: 385.720
Hydration Free Energy: -6.840
Log(D) at pH=7.4: 2.540
Log(P): 2.71
Log S: -2.16
Log(Vapor Pressure): -6.51
Melting Point: 148.55
pKa Acid: 11.78
pKa Basic: 7.56

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	0.9818
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9818
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9062
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9062
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8994
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8994
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8942
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8942
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8797
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8797
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8670
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8670
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8667
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8667
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8570
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8570
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8529
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8529
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8452
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8452
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8450
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8450
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8429
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8429
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8325
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8325
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8283
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8283
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8126
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8126
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8027
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8027
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7950
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7950
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7828
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7828
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7744
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7744
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7738
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7738
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7639
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7639
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7626
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7626
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7617
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7617
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7611
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7611
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7608
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7608
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7605
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7605
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7546
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7546
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7540
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7540
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7521
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7521
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7492
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7492
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7460
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7460
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7460
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7460
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7418
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7418
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7389
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7389
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7379
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7379
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	3	0.7362
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	3	0.7362
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7352
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7352
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7309
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7309
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7304
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7304
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7270
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7270
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7269
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7269
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7258
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7258
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7244
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7244
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7243
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7243
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7240
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7240
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7200
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7200
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7195
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7195
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7193
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7193
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7185
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7185
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7174
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7174
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7160
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7160
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7156
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7156
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7145
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7145
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7130
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7130
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7123
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7123
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7119
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7119
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7111
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7111
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7102
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7102
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7088
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7088
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7080
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7080
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7073
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7073
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7046
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7046
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7032
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7032
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7030
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7030
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7030
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7030
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7018
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7018

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