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Maemesin

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Furanoflavone

Canonical Smiles	O=c1ccc2c(o1)cc1c(c2)C[C@@H](O1)C(O)(C)C
InChI	InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m1/s1
InChIKey	FWYSBEAFFPBAQU-GFCCVEGCSA-N
Formula	C₁₄H₁₄O₄
HBA	4
HBD	1
MW	246.26
Rotatable Bonds	1
TPSA	59.67
LogP	1.87
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	246.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrus reticulata	Rutaceae	Plantae	85571

Showing of synonyms

Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]

Pubchem: 26305

Cas: 495-32-9

Gnps: CCMSLIB00006458556

Zinc: ZINC000000051923

Kegg Ligand: C09278

Chebi: 132623

Nmrshiftdb2: 60021979

Metabolights: MTBLC132623

Chembl: CHEMBL1464240

CPRiL: 132670

SMILES: C1COc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 246.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.140
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 61.26
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.180
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.390
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.130
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: 2.150
Rat (Acute): 2.350
Rat (Chronic Oral): 1.390
Fathead Minnow: 4.140
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 366.290
Hydration Free Energy: -10.450
Log(D) at pH=7.4: 1.640
Log(P): 1.69
Log S: -2.94
Log(Vapor Pressure): -6.6
Melting Point: 206.58
pKa Acid: 6.81
pKa Basic: 6.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9656
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9420
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9412
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.9099
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9027
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9024
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8914
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8908
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8863
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8848
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8845
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8812
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8797
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8751
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8749
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8733
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8727
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8657
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8640
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8614
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.8591
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8527
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8464
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8462
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8450
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8374
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8253
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8236
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8202
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8200
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8198
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8195
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8158
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8120
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.8065
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.8033
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8032
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8031
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8017
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7950
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7940
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7926
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7918
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7893
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7884
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7861
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7860
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7834
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7800
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7740
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7701
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7694
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7656
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7624
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7616
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7616
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7608
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7600
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7587
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7578
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7544
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.7524
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7524
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7521
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7481
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7480
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7471
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7469
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7467
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7464
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7455
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7447
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7445
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7437
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7430
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7430
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7417
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7409
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7405
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7403
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7399
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7396
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7394
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7392
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7388
Androgen receptor	P19091	ANDR_MOUSE	Mus musculus	3	0.7387
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7365
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7364
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7360
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7356
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7356
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7356
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7349
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7348
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7346
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7338
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7338
Avidin	P02701	AVID_CHICK	Gallus gallus	4	0.7337
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7332
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7332
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7330
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7330
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7316
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7313
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7309
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7300
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7295
DNA double-strand break repair protein Mre11	Q9X1X0	Q9X1X0_THEMA	Thermotoga maritima MSB8	3	0.7292
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7287
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7286
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7284
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.7281
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7277
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	2	0.7277
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7276
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7269
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7265
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7262
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7260
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7260
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7258
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7256
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7251
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7246
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7243
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7236
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7229
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7220
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7219
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7215
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7207
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7203
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7201
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7200
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7191
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7190
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7188
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7186
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7174
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7161
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7160
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7157
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7155
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7153
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7152
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7150
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7150
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7140
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7135
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7133
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7133
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7113
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7096
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7089
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7089
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7087
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7081
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7069
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7057
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7055
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7048
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7043
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7039
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7034
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7029
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7024
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7012

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