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Erybreadin D

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

Canonical Smiles	CC(=CCc1c(O)ccc2c1OC[C@@H]1[C@H]2Oc2c1ccc1c2OC(C)(C)C=C1)C
InChI	InChI=1S/C25H26O4/c1-14(2)5-7-17-20(26)10-9-18-22(17)27-13-19-16-8-6-15-11-12-25(3,4)29-21(15)24(16)28-23(18)19/h5-6,8-12,19,23,26H,7,13H2,1-4H3/t19-,23-/m0/s1
InChIKey	YODBFZQPDZJGJG-CVDCTZTESA-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: 46880036

Zinc: ZINC000049111725

Nmrshiftdb2: 60046510

Chembl: CHEMBL1087148

Bindingdb: 50311580

No compound-protein relationship available.

SMILES: O1CC=Cc(cc2)c1c(c23)OC4C3COc5c4cccc5

Level: 0

Mol. Weight: 390.48 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.98
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.55
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.15
Plasma Protein Binding: 89.51
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: Non-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: 8.64
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.81
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.03
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.79
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: -24.28
Rat (Acute): 2.45
Rat (Chronic Oral): 1.78
Fathead Minnow: 5.21
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 471.46
Hydration Free Energy: -5.05
Log(D) at pH=7.4: 4.24
Log(P): 6.21
Log S: -5.62
Log(Vapor Pressure): -8.87
Melting Point: 177.93
pKa Acid: 10.4
pKa Basic: 7.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8834
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8699
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8493
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8160
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8011
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8004
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7798
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7739
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7736
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7719
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7663
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7635
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7448
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7406
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7376
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7302
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7277
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7263
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7231
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7227
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7216
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7215
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7213
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7176
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7155
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7115
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7041
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7040
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7032
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7023
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7017
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7004

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