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Erybreadin B

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Pterocarpan

Canonical Smiles	CC(=CCc1c(O)ccc2c1OC[C@@H]1[C@H]2Oc2c1ccc1c2C=CC(O1)(C)C)C
InChI	InChI=1S/C25H26O4/c1-14(2)5-6-16-20(26)9-7-18-22(16)27-13-19-15-8-10-21-17(23(15)28-24(18)19)11-12-25(3,4)29-21/h5,7-12,19,24,26H,6,13H2,1-4H3/t19-,24-/m0/s1
InChIKey	XDRMVDDOBVPELW-CYFREDJKSA-N
Formula	C₂₅H₂₆O₄
HBA	4
HBD	1
MW	390.48
Rotatable Bonds	2
TPSA	47.92
LogP	5.69
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	390.18
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina abyssinica	Leguminosae/Fabaceae	Plantae	1237573

Showing of synonyms

Nguyen PH, Le TV, et al. (2009). Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorganic & medicinal chemistry letters,2009, 19(23), 6745-9. [View] [PubMed]

Pubchem: 45268827

Zinc: ZINC000015203440

Nmrshiftdb2: 60046373

Chembl: CHEMBL561967

Bindingdb: 50311577

No compound-protein relationship available.

SMILES: C1=CCOc(cc2)c1c(c23)OC4C3COc5c4cccc5

Level: 0

Mol. Weight: 390.48 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.92
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.51
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.11
Plasma Protein Binding: 87.28
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: 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: 8.41
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.62
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.23
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.26
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -24.02
Rat (Acute): 2.36
Rat (Chronic Oral): 1.7
Fathead Minnow: 5.23
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 475.79
Hydration Free Energy: -5.1
Log(D) at pH=7.4: 4.42
Log(P): 6.33
Log S: -5.69
Log(Vapor Pressure): -8.96
Melting Point: 172.72
pKa Acid: 11.05
pKa Basic: 8.05

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8852
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8732
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8592
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8519
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8120
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7952
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7816
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7811
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7765
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7659
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7539
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7475
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7426
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7415
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7408
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7358
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7349
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7345
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7344
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7291
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7283
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7240
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7235
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7228
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7164
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7133
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7130
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7109
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7104
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7099
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7064
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7062

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