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Ovatifolionone

Family: Plantae - Hyacinthaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Homoisoflavonoid

Canonical Smiles	Oc1cc(O)c2c(c1)OC/C(=C\c1ccc(c(c1)O)O)/C2=O
InChI	InChI=1S/C16H12O6/c17-10-5-13(20)15-14(6-10)22-7-9(16(15)21)3-8-1-2-11(18)12(19)4-8/h1-6,17-20H,7H2/b9-3+
InChIKey	GSXUMSFRTKYHFT-YCRREMRBSA-N
Formula	C₁₆H₁₂O₆
HBA	6
HBD	4
MW	300.27
Rotatable Bonds	1
TPSA	107.22
LogP	2.17
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.06
Exact Mass	300.06
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ledebouria ovatifolia	Hyacinthaceae	Plantae	1069013

Showing of synonyms

Waller CP, Thumser AE, et al. (2013). COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 2013, 95, 284–290. [View]

Pubchem: 155515358

Zinc: ZINC000238786118

Chembl: CHEMBL4442174

No compound-protein relationship available.

SMILES: c1ccccc1C=C(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 300.27 g/mol

SMILES: O=C1C(=C)COc(c12)cccc2

Level: 0

Mol. Weight: 300.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.13
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.97
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.93
Plasma Protein Binding: 73.61
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.17
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.29
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.1
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.55
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 4.98
Rat (Acute): 2.25
Rat (Chronic Oral): 2.94
Fathead Minnow: 4.54
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: 479.0
Hydration Free Energy: -11.78
Log(D) at pH=7.4: 2.04
Log(P): 2.41
Log S: -4.72
Log(Vapor Pressure): -8.73
Melting Point: 260.17
pKa Acid: 5.65
pKa Basic: 7.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9374
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.9342
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9272
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9173
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.9023
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8994
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8950
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	3	0.8925
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8675
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8665
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8641
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8569
BH2602 protein	Q9K9P3	Q9K9P3_BACHD	Bacillus halodurans	3	0.8568
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8532
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8521
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8501
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8386
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8338
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8297
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8243
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8237
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8236
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.8174
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8172
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8140
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8096
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.8065
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8038
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7958
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7932
BMP-2-inducible protein kinase	Q9NSY1	BMP2K_HUMAN	Homo sapiens	3	0.7928
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7800
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7799
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7797
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7784
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7762
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.7715
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7676
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7641
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7632
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.7624
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7617
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7612
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7594
Bifunctional AAC/APH	P0A0C1	AACA_STAAU	Staphylococcus aureus	4	0.7578
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7574
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7552
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7547
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7524
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7518
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7496
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7495
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	4	0.7492
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7462
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7460
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7457
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7455
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7419
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7414
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7408
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7400
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7394
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7339
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7322
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7317
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7315
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7309
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7274
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7248
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7238
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7234
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7206
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	3	0.7193
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7181
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7163
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7160
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7125
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7123
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7122
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7118
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7096
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7081
PTS system glucose-specific EIIA component	P69783	PTGA_ECOLI	Escherichia coli	3	0.7078
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7069
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7067
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7046
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	4	0.7036
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7035
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7022
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7014
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7009
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7006
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7003

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