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Erysovine

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

Canonical Smiles	CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc(O)c(cc1CC3)OC
InChI	InChI=1S/C18H21NO3/c1-21-14-4-3-13-6-8-19-7-5-12-9-17(22-2)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-/m0/s1
InChIKey	IHPMURIXWRKEKD-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 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]

Pubchem: 5317203

Cas: 466-72-8

Gnps: CCMSLIB00000081227

Zinc: ZINC000015203660

Nmrshiftdb2: 60024894

Chembl: CHEMBL517778

No compound-protein relationship available.

SMILES: C1CC=CC(C123)=CCN3CCc4c2cccc4

Level: 0

Mol. Weight: 299.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.700
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.490
Plasma Protein Binding: 37.1
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: 8.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.490
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: 10.040
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: -3.380
Rat (Acute): 2.930
Rat (Chronic Oral): 1.840
Fathead Minnow: 4.080
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: 363.510
Hydration Free Energy: -8.290
Log(D) at pH=7.4: 1.860
Log(P): 1.98
Log S: -1.48
Log(Vapor Pressure): -6.11
Melting Point: 181.94
pKa Acid: 9.86
pKa Basic: 7.66

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	0.9671
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9435
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9346
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9184
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.9135
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9114
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9104
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9036
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8905
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8901
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8836
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8826
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8791
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8777
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8733
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8674
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8595
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8520
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8472
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8448
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8442
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8433
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8426
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8419
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8362
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8344
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8242
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8058
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8004
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7985
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7959
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7821
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7817
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7806
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7801
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7782
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7735
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.7680
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7647
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7641
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7626
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7616
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7614
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7613
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7575
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7524
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7512
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7466
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7451
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7415
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7414
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7363
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7317
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7312
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7311
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7310
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7303
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7289
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7286
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7279
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7261
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7259
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7247
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7240
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7237
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7228
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7200
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.7173
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7164
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7160
Ribosomal RNA small subunit methyltransferase Nep1	Q57977	NEP1_METJA	Methanocaldococcus jannaschii	3	0.7150
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7122
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7122
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	3	0.7110
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7104
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7102
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7097
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7075
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	2	0.7071
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7062
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7057
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7056
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7053
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7051
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7039
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7037
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7026
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7020
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7018
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7016
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7009

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