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Luteone

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	CC(=CCc1c(O)cc2c(c1O)c(=O)c(co2)c1ccc(cc1O)O)C
InChI	InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3
InChIKey	MMPVAPMCVABQPS-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₆
HBA	6
HBD	4
MW	354.36
Rotatable Bonds	3
TPSA	111.13
LogP	3.79
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	354.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus thonningii	Moraceae	Plantae	309310

Showing of synonyms

Fongang Y, Bankeu J, et al. (2015). Flavonoids and other bioactive constituents from Ficus thonningii Blume (Moraceae). Phytochemistry Letters, 2015, 11, 139-145. [View]

Pubchem: 5281797

Cas: 41743-56-0

Zinc: ZINC000005854353

Kegg Ligand: C10498

Chebi: 27917

Nmrshiftdb2: 60066119

Metabolights: MTBLC27917

Chembl: CHEMBL549617

Comptox: DTXSID00194574

No compound-protein relationship available.

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 354.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 354.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.02
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 82.63
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 4.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.56
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.99
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.56
Rat (Acute): 2.43
Rat (Chronic Oral): 3.12
Fathead Minnow: 4.86
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 500.87
Hydration Free Energy: -12.09
Log(D) at pH=7.4: 3.46
Log(P): 4.78
Log S: -5.67
Log(Vapor Pressure): -9.18
Melting Point: 230.49
pKa Acid: 5.52
pKa Basic: 7.19

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9522
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9301
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9156
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9095
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.9069
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8922
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8883
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8835
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8822
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.8818
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8703
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8509
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8504
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8491
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8455
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8451
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8433
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8414
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.8409
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8297
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8295
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8273
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.8250
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8247
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8149
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8127
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8102
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8069
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8018
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7996
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7992
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7983
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7940
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7856
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7843
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7783
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7780
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7754
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.7741
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7740
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7736
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7727
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7708
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7707
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7691
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7653
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7646
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7614
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7604
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7588
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7588
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7585
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7564
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7547
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7531
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7527
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7523
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7480
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7479
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7473
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7471
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7466
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7448
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7447
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7442
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7429
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	3	0.7383
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7379
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7374
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7364
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7352
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7323
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	4	0.7288
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7285
Bifunctional dihydrofolate reductase-thymidylate synthase	D9N170	D9N170_PLAFA	Plasmodium falciparum	4	0.7272
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7270
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7269
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7266
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7264
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7260
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7255
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7249
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7243
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7220
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7219
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7218
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7213
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7213
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7204
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7164
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7135
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7133
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7128
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7126
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7124
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7122
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7122
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7113
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7112
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7110
Protease	O38708	O38708_9HIV1	Human immunodeficiency virus 1	3	0.7101
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7083
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7081
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7076
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7075
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	4	0.7071
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7062
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7046
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7030
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7021
Enoyl-acyl carrier protein reductase	Q6TEI5	Q6TEI5_PLABE	Plasmodium berghei	4	0.7020
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7016
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7013
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7013
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7011
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7008
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	2	0.7003

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