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Erysovine -N-oxide

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

Canonical Smiles	CO[C@H]1C=CC2=CC[N@@]3(=O)[C@]2(C1)c1cc(O)c(cc1CC3)OC
InChI	InChI=1S/C18H21NO4/c1-22-14-4-3-13-6-8-19(21)7-5-12-9-17(23-2)16(20)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-,19+/m0/s1
InChIKey	GUTBSIAKRDWCHI-ZOCIIQOWSA-N
Formula	C₁₈H₂₁NO₄
HBA	4
HBD	1
MW	315.37
Rotatable Bonds	2
TPSA	61.75
LogP	2.38
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	315.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina addisoniae	Leguminosae/Fabaceae	Plantae	2590682

Showing of synonyms

Cui L, Thuong PT, et al. (2009). A new Erythrinan alkaloid from the seed of Erythrina addisoniae.. Archives of pharmacal research,2009, 32(3), 325-328. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1CC=CC(C123)=CCN3(=O)CCc4c2cccc4

Level: 0

Mol. Weight: 315.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.32
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.640
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.470
Plasma Protein Binding: 60.01
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.690
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.410
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.220
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.450
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: -1.450
Rat (Acute): 2.440
Rat (Chronic Oral): 1.650
Fathead Minnow: 4.000
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 379.840
Hydration Free Energy: -8.130
Log(D) at pH=7.4: 1.770
Log(P): 0.22
Log S: -0.49
Log(Vapor Pressure): -7.36
Melting Point: 230.36
pKa Acid: 7.01
pKa Basic: 2.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9434
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	3	0.9126
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8997
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8911
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8807
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8738
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8682
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8625
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8590
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8586
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic	O96693	DXR_PLAFX	Plasmodium falciparum	3	0.8564
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8553
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8436
Tryptophan synthase beta chain 2	Q97TX6	TRPB2_SACS2	Saccharolobus solfataricus	3	0.8433
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8432
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8429
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8378
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8346
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8303
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8251
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7960
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7886
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7886
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7858
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7826
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7820
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7772
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7768
Cysteine desulfurase IscS 2	O29689	ISCS2_ARCFU	Archaeoglobus fulgidus	3	0.7640
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7517
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7494
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7492
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7449
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7446
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7404
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7394
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7392
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7389
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7363
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7361
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7341
HD domain protein	Q836G9	Q836G9_ENTFA	Enterococcus faecalis	3	0.7305
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.7299
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7298
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7297
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7296
Cysteine desulfurase IscS 2	O29689	ISCS2_ARCFU	Archaeoglobus fulgidus	3	0.7292
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7281
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7252
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7249
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7245
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7244
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	3	0.7234
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7232
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7155
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7149
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7138
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7132
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7115
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7104
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7101
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	2	0.7099
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7073
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7061
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7060
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7055
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7055
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7053
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7041
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7040
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7036
Biotin carboxylase	P43873	ACCC_HAEIN	Haemophilus influenzae	3	0.7033
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7031
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7019
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7019
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7003

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