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Glyinflanin H

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Benzofuran
- Subclass: Arylbenzofuran

Canonical Smiles	Oc1ccc2c(c1)oc(c2)c1ccc2c(c1O)C=CC(O2)(C)C
InChI	InChI=1S/C19H16O4/c1-19(2)8-7-14-15(23-19)6-5-13(18(14)21)17-9-11-3-4-12(20)10-16(11)22-17/h3-10,20-21H,1-2H3
InChIKey	AOVQEAUIBICOLQ-UHFFFAOYSA-N
Formula	C₁₉H₁₆O₄
HBA	4
HBD	2
MW	308.33
Rotatable Bonds	1
TPSA	62.83
LogP	4.7
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	308.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina addisoniae	Leguminosae/Fabaceae	Plantae	2590682

Showing of synonyms

Na M, Hoang DM, et al. (2007). Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B.. Bioorganic & medicinal chemistry letters,2007, 17(14), 3868-3871. [View] [PubMed]

Pubchem: 15233562

Cas: 164123-54-0

Chebi: 85109

Nmrshiftdb2: 70042805

Metabolights: MTBLC85109

Chembl: CHEMBL233766

Bindingdb: 50213491

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(c2)-c(c3)ccc(c34)OCC=C4

Level: 1

Mol. Weight: 308.33 g/mol

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 308.33 g/mol

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 308.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.880
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.910
Plasma Protein Binding: 61.0
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.520
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 2.190
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.130
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.770
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.280
Rat (Acute): 2.530
Rat (Chronic Oral): 2.330
Fathead Minnow: 4.880
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 440.770
Hydration Free Energy: -11.110
Log(D) at pH=7.4: 4.420
Log(P): 5.2
Log S: -5.19
Log(Vapor Pressure): -8.92
Melting Point: 228.15
pKa Acid: 7.96
pKa Basic: 5.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9683
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9616
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9498
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9414
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.9358
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9335
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9289
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8933
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8852
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.8833
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8830
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.8513
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8458
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8283
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8224
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8219
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8145
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8102
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8100
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8079
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.7888
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7888
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7881
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7879
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7817
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7720
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7706
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7688
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7677
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7676
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7638
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7636
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7635
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7620
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7616
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7595
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7551
Nuclear hormone receptor of the steroid/thyroid hormone receptors superfamily	Q9XZJ5	Q9XZJ5_STRER	Strongyloides stercoralis	4	0.7470
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7462
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7451
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7386
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7344
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7344
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7304
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7304
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7300
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7246
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7244
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7241
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7209
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7192
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7191
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7180
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7169
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7168
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7141
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7128
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7117
Endochitinase B1	Q873X9	CHIB1_ASPFM	Aspergillus fumigatus	4	0.7112
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7108
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7105
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7099
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7087
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7086
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7075
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7063
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7052
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7050
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7035
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7019
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.7014
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7010

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