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Erysopine

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)O
InChI	InChI=1S/C17H19NO3/c1-21-13-3-2-12-5-7-18-6-4-11-8-15(19)16(20)9-14(11)17(12,18)10-13/h2-3,5,8-9,13,19-20H,4,6-7,10H2,1H3/t13-,17-/m0/s1
InChIKey	GNBQGLMYBIWCOO-GUYCJALGSA-N
Formula	C₁₇H₁₉NO₃
HBA	4
HBD	2
MW	285.34
Rotatable Bonds	1
TPSA	52.93
LogP	2.07
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	285.14
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: 21679844

Nmrshiftdb2: 60073911

No compound-protein relationship available.

SMILES: C1CC=CC(C123)=CCN3CCc4c2cccc4

Level: 0

Mol. Weight: 285.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.98
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.410
Plasma Protein Binding: 37.42
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: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 16.830
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.270
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.220
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 7.170
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: -0.740
Rat (Acute): 2.440
Rat (Chronic Oral): 2.300
Fathead Minnow: 3.970
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: 377.700
Hydration Free Energy: -10.110
Log(D) at pH=7.4: 0.830
Log(P): 1.69
Log S: -1.84
Log(Vapor Pressure): -7.15
Melting Point: 213.59
pKa Acid: 9.03
pKa Basic: 6.92

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	0.9536
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9061
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8926
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8920
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8744
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8694
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8657
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8543
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8489
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	3	0.8428
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8420
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8410
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8406
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8323
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8305
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8263
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8217
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8215
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8095
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8065
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8048
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8008
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8005
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7954
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7869
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7783
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7778
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7757
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7749
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7728
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7700
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7610
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7549
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7511
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7497
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7486
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7466
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7416
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7401
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7365
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7359
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7355
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7340
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7318
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7316
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7303
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7288
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7263
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7262
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7237
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7236
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7221
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7191
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7158
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7153
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7139
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7136
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7134
Petrobactin biosynthesis protein AsbB	Q81RQ8	Q81RQ8_BACAN	Bacillus anthracis	3	0.7117
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7104
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7100
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7085
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7079
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7079
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7061
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7060
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7055
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7053
Ribosomal RNA small subunit methyltransferase Nep1	Q57977	NEP1_METJA	Methanocaldococcus jannaschii	3	0.7027

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