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Abyssinin III

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

Canonical Smiles	CC(=CCc1c(cc(c(c1CC=C(C)C)O)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)C
InChI	InChI=1S/C25H28O6/c1-13(2)5-7-16-17(8-6-14(3)4)25(30)21(29)11-18(16)22-12-20(28)24-19(27)9-15(26)10-23(24)31-22/h5-6,9-11,22,26-27,29-30H,7-8,12H2,1-4H3/t22-/m0/s1
InChIKey	TVXYDDJFAOWCAE-QFIPXVFZSA-N
Formula	C₂₅H₂₈O₆
HBA	6
HBD	4
MW	424.49
Rotatable Bonds	5
TPSA	107.22
LogP	5.23
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	424.19
Number of Lipinski Rule Violations	1

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

Showing of synonyms

Yenesew A, Twinomuhwezi H, et al. (2009). 8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica.. Bulletin of the Chemical Society of Ethiopia,2009,23(2),205-210. [View] [PubMed]
Yenesew A, Induli M, et al. (2004). Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica.. Phytochemistry,2004,65(22),3029-3032. [View] [PubMed]
Ichimaru M, Moriyasu M, et al. (1996). Structural Elucidation of New Flavanones Isolated from Erythrina abyssinica.. Journal of Natural Products,1996,59,1113-1116. [View] [PubMed]

Pubchem: 15293189

Nmrshiftdb2: 60073036

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 424.49 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 424.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.49 g/mol

Anti-plasmodial

Radical scavenging towards 2;2-diphenyl-1-picrylhydrazyl radical (dpph)

Absorption

Caco-2 (logPapp): -5.72
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.0
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.96
Plasma Protein Binding: 83.07
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-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: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.85
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.18
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.36
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.28
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -23.52
Rat (Acute): 2.12
Rat (Chronic Oral): 3.37
Fathead Minnow: 5.23
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: 504.3
Hydration Free Energy: -6.09
Log(D) at pH=7.4: 3.08
Log(P): 5.57
Log S: -6.36
Log(Vapor Pressure): -8.81
Melting Point: 198.4
pKa Acid: 8.24
pKa Basic: 6.82

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9006
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9006
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8920
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8920
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8911
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8911
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8881
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8881
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8539
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8539
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8471
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8471
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8456
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8456
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8431
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8431
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8361
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8361
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8325
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8325
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8274
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8274
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8214
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8214
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8097
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8097
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8069
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8069
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8047
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8047
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8008
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8008
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8007
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8007
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7982
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7982
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7936
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7936
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7900
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7900
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7889
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7889
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7799
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7799
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7757
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7757
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7757
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7757
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7738
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7738
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7725
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7725
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7706
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7706
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7681
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7681
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7666
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7666
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7653
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7653
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7651
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7651
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7648
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7648
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7590
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7590
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7569
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7569
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7537
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7537
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7515
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7515
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7510
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7510
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7510
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7510
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7496
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7496
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7454
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7454
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7447
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7447
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7443
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7443
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7405
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7405
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7367
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7367
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7349
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7349
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7346
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7346
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7320
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7320
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7296
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7296
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7287
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7287
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7284
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7284
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7272
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7272
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7241
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7241
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7237
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7237
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7236
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7236
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7234
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7234
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7227
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7227
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7219
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7219
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7188
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7188
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7184
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7184
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7177
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7177
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7161
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7161
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7153
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7153
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7129
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7129
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7120
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7120
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7118
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7118
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7102
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7102
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7097
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7097
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7096
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7096
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7087
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7087
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7083
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7083
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7081
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7081
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7067
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7067
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7046
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7046
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7023
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7023
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7010
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7010

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