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Erythribyssin C

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

Canonical Smiles	COc1cc2OC[C@@H]3[C@H](c2cc1CC=C(C)C)Oc1c3cc(c(c1)O)OC
InChI	InChI=1S/C22H24O5/c1-12(2)5-6-13-7-15-19(10-18(13)24-3)26-11-16-14-8-21(25-4)17(23)9-20(14)27-22(15)16/h5,7-10,16,22-23H,6,11H2,1-4H3/t16-,22-/m0/s1
InChIKey	YBJTWUNILZOAFZ-AOMKIAJQSA-N
Formula	C₂₂H₂₄O₅
HBA	5
HBD	1
MW	368.43
Rotatable Bonds	4
TPSA	57.15
LogP	4.53
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: 45375877

Zinc: ZINC000049109756

Nmrshiftdb2: 60046506

Chembl: CHEMBL1079407

Bindingdb: 50311574

No compound-protein relationship available.

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 368.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.580
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.250
Plasma Protein Binding: 85.21
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: 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: 9.500
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.920
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.380
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: -6.420
Rat (Acute): 2.030
Rat (Chronic Oral): 2.130
Fathead Minnow: 5.120
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: 446.210
Hydration Free Energy: -5.990
Log(D) at pH=7.4: 3.750
Log(P): 4.46
Log S: -5.56
Log(Vapor Pressure): -8.03
Melting Point: 169.8
pKa Acid: 10.33
pKa Basic: 7.06

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9549
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9467
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9423
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9320
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9274
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9233
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9205
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9047
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8983
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8974
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8961
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8920
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8784
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8748
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8679
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8610
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.8598
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8569
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8536
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.8456
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8366
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8329
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8325
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8302
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8294
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8243
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8198
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8146
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8065
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8061
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8053
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8032
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8023
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7978
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7977
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7957
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7957
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7871
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7794
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7786
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7747
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7732
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7718
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7717
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7716
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7714
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7709
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7705
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7684
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7672
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7671
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7668
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7664
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7664
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7657
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7644
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7633
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7625
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7616
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7613
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7532
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7525
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7521
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7503
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7490
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7485
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7480
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7464
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7456
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7448
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7445
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7442
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7438
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7436
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7432
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	3	0.7411
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7409
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7398
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7395
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7367
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7361
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7349
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7347
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7336
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7320
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7319
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7316
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7313
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7308
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7282
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7281
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7269
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7265
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7244
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7242
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7231
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7227
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7226
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7190
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7188
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7186
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7186
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7183
ADP-ribosylation factor-like protein 3	A8ISN6	ARL3_CHLRE	Chlamydomonas reinhardtii	4	0.7172
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7159
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7139
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7132
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7128
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	4	0.7124
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7121
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7120
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7119
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7111
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7110
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7109
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7108
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7104
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7100
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7093
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7091
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7089
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7088
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7088
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7087
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7085
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7083
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7077
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7076
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7067
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7060
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7055
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7048
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7045
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7039
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7036
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7033
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7030
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7023
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7019
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	4	0.7014
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7014
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7004
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7002

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