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Mearnsetin

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

Canonical Smiles	COc1c(O)cc(cc1O)c1oc2cc(O)cc(c2c(=O)c1O)O
InChI	InChI=1S/C16H12O8/c1-23-16-9(19)2-6(3-10(16)20)15-14(22)13(21)12-8(18)4-7(17)5-11(12)24-15/h2-5,17-20,22H,1H3
InChIKey	HKEQVXVLTOSXLQ-UHFFFAOYSA-N
Formula	C₁₆H₁₂O₈
HBA	8
HBD	5
MW	332.26
Rotatable Bonds	2
TPSA	140.59
LogP	2.0
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.06
Exact Mass	332.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Imperata cylindrica	Gramineae	Plantae	80369
2	Dioclea reflexa	Leguminosae/Fabaceae	Plantae	2986840

Showing of synonyms

Oladimeji AO, OladosuI A, et al. (2015). Flavonoids from the roots of Dioclea reflexa (HOOK F.). Bulletin of the Chemical Society of Ethiopia,2015,29 (3),441-448.. [View]
Nago RDT, Nayim P, et al. (2021). Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae). Molecules. 2021, 26(16), 4717. [View] [PubMed]

Pubchem: 10359384

Cas: 16805-10-0

Zinc: ZINC000013838618

Chebi: 196346

Nmrshiftdb2: 60014622

Chembl: CHEMBL484633

Comptox: DTXSID20438720

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 332.26 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 332.26 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 332.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.440
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.22

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.930
Plasma Protein Binding: 93.87
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.680
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.150
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.480
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.290
Micronucleos: Toxic
NR-AhR: Toxic
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: Safe
T. Pyriformis: 2.730
Rat (Acute): 2.470
Rat (Chronic Oral): 3.570
Fathead Minnow: 3.910
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 515.140
Hydration Free Energy: -10.390
Log(D) at pH=7.4: 1.910
Log(P): 1.34
Log S: -4.57
Log(Vapor Pressure): -7.39
Melting Point: 281.4
pKa Acid: 6.24
pKa Basic: 5.3

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9079
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9058
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8885
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8866
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8827
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.8790
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8787
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8781
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8774
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8697
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8681
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8673
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8628
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8622
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.8594
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8553
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8518
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8518
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8506
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8501
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8486
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.8466
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8459
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8442
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8429
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8379
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8366
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8357
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8348
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8312
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8302
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8288
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8263
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8255
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8250
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	5	0.8245
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8238
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8219
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8218
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	5	0.8207
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8192
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8139
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8123
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8074
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8070
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8061
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8051
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8037
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8029
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8027
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8001
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7974
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	5	0.7917
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7915
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7903
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7899
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7856
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7851
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7832
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7830
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7826
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7813
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7781
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7767
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7722
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7702
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7680
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7678
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7663
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7637
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7631
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7624
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7622
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7590
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7582
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7580
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7570
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7567
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7563
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7560
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.7544
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7542
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7539
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7459
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7452
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7429
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7429
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7428
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7409
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7409
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7406
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7400
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7397
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7397
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7397
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7393
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7367
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7365
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7364
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7360
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7350
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7343
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7337
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7323
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7322
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7317
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7301
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	6	0.7293
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7273
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7264
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7262
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7226
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7219
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7210
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7206
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7189
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7176
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7173
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7169
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7167
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7165
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7159
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7149
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7146
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7134
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7133
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7124
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7121
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7119
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7113
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7109
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7105
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7104
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7103
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7099
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7097
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7093
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7087
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7085
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7081
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7067
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7058
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7057
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	4	0.7056
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7053
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7041
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.7025
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7003

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