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Erythribyssin A

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

Canonical Smiles	CO[C@]12COc3c([C@@H]2Oc2c1ccc(c2CC=C(C)C)OC)ccc(c3)O
InChI	InChI=1S/C22H24O5/c1-13(2)5-7-15-18(24-3)10-9-17-20(15)27-21-16-8-6-14(23)11-19(16)26-12-22(17,21)25-4/h5-6,8-11,21,23H,7,12H2,1-4H3/t21-,22+/m0/s1
InChIKey	IGSYALWDCAHJEF-FCHUYYIVSA-N
Formula	C₂₂H₂₄O₅
HBA	5
HBD	1
MW	368.43
Rotatable Bonds	4
TPSA	57.15
LogP	4.28
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	368.16
Number of Lipinski Rule Violations	0

#	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: 46879996

Zinc: ZINC000049049444

Nmrshiftdb2: 60046507

Chembl: CHEMBL1076430

Bindingdb: 50311572

No compound-protein relationship available.

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 368.43 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.91
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.57
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.1
Plasma Protein Binding: 88.62
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-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: 8.68
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.59
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.9
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: -6.08
Rat (Acute): 2.11
Rat (Chronic Oral): 1.77
Fathead Minnow: 5.16
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 449.43
Hydration Free Energy: -5.91
Log(D) at pH=7.4: 3.46
Log(P): 4.56
Log S: -5.08
Log(Vapor Pressure): -8.05
Melting Point: 165.54
pKa Acid: 10.52
pKa Basic: 6.55

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	0.9403
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9368
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9353
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9110
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8979
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8936
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8918
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.8895
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8884
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8794
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8548
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8537
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8465
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8454
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.8414
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8399
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8395
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.8386
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8354
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8236
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8152
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8141
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8113
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8074
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8062
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8013
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8011
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7993
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7993
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7986
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7983
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7973
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7958
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7860
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7857
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7688
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7663
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7656
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7623
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7597
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7592
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7580
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7573
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	3	0.7571
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7534
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7510
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7508
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7493
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7484
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7472
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7468
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7455
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7443
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7437
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7434
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7421
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7416
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7411
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7401
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7401
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7386
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7348
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7345
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7341
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7339
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7329
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7322
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7305
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7290
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7280
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7280
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7275
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7270
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7239
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7236
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7227
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7209
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7204
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7175
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7158
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7155
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7151
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7148
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7125
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7119
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7078
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7075
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7068
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7060
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7041
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7036
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7031
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7023
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7023
Phosphatidylinositol 3-kinase catalytic subunit type 3	Q8NEB9	PK3C3_HUMAN	Homo sapiens	4	0.7019
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7016

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