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

Canonical Smiles	CC(=CCc1cc2c(cc1O)OC[C@@H]1[C@H]2Oc2c1ccc1c2C=CC(O1)(C)C)C
InChI	InChI=1S/C25H26O4/c1-14(2)5-6-15-11-18-22(12-20(15)26)27-13-19-16-7-8-21-17(23(16)28-24(18)19)9-10-25(3,4)29-21/h5,7-12,19,24,26H,6,13H2,1-4H3/t19-,24-/m0/s1
InChIKey	XERSCIKBWOLVNC-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: 15840592

Cas: 26992-37-0

Nmrshiftdb2: 70129312

Chembl: CHEMBL551155

Bindingdb: 50311579

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): -4.94
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.54
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.13
Plasma Protein Binding: 89.26
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: 8.22
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.95
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.37
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.22
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: -23.48
Rat (Acute): 2.32
Rat (Chronic Oral): 1.61
Fathead Minnow: 5.26
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: 480.32
Hydration Free Energy: -5.31
Log(D) at pH=7.4: 4.43
Log(P): 6.22
Log S: -5.89
Log(Vapor Pressure): -9.58
Melting Point: 185.48
pKa Acid: 11.43
pKa Basic: 7.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9391
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9389
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9226
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9140
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8849
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8720
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8667
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8647
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8642
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8449
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8254
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8192
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8185
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8114
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8017
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7721
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7682
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7633
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7537
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7522
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7493
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7469
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7450
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7442
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7440
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7417
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7416
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7412
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7393
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7393
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7347
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7347
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7346
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7331
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7271
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7245
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7202
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7200
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7159
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7154
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7140
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7132
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7120
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7116
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7109
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7088
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7084
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7077
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7076
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7047
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7039
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7021

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