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Lemairone A

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

Canonical Smiles	Oc1ccc(cc1)[C@@H]1Oc2cc(cc(c2C(=O)[C@H]1c1c(O)cc(c2c1O[C@@H](c1ccc(c(c1)O)O)[C@@H](C2=O)O)O)O)Oc1cc(O)c2c(c1[C@@H]1[C@H](Oc3c(C1=O)c(O)cc(c3)O)c1ccc(cc1)O)O[C@@H]([C@H](C2=O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C60H42O23/c61-25-7-1-21(2-8-25)55-47(43-35(70)19-36(71)44-51(75)53(77)57(82-59(43)44)23-5-11-29(64)31(66)13-23)49(73)42-34(69)17-28(18-39(42)81-55)79-40-20-37(72)45-52(76)54(78)58(24-6-12-30(65)32(67)14-24)83-60(45)46(40)48-50(74)41-33(68)15-27(63)16-38(41)80-56(48)22-3-9-26(62)10-4-22/h1-20,47-48,53-58,61-72,77-78H/t47-,48+,53-,54+,55+,56-,57+,58-/m1/s1
InChIKey	ZUQDXJWFTOVBGG-JKSQYWPGSA-N
Formula	C₆₀H₄₂O₂₃
HBA	23
HBD	14
MW	1130.97
Rotatable Bonds	8
TPSA	397.65
LogP	7.5
Number Rings	12
Number Aromatic Rings	8
Heavy Atom Count	83
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	1130.21
Number of Lipinski Rule Violations	4

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zanthoxylum lemairei	Rutaceae	Plantae	2099535

Showing of synonyms

Bitchagno G, Tankeo S, et al. (2015). Lemairones A and B: Two new antibacterial tetraflavonoids from the leaves of Zanthoxylum lemairei (Rutaceae). Phytochemistry Letters, 2015, 14, 1-7. [View]

Pubchem: 132556531

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OC(c9ccccc9)C(C8=O)c(ccc1)c(c12)OC(CC2=O)c1ccccc1

Level: 7

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OC(c8ccccc8)C(C7=O)c(ccc9)c(c19)OC(CC1=O)c1ccccc1

Level: 6

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OCC(C8=O)c(ccc9)c(c19)OC(CC1=O)c1ccccc1

Level: 6

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OC(c9ccccc9)C(C8=O)c(ccc1)c(c12)OCCC2=O

Level: 6

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OC(c8ccccc8)C(C7=O)c(ccc9)c(c19)OC(CC1=O)c1ccccc1

Level: 6

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OCC(C7=O)c(ccc8)c(c89)OC(CC9=O)c1ccccc1

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OC(c8ccccc8)C(C7=O)c(ccc9)c(c19)OCCC1=O

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OCC(C8=O)c(ccc9)c(c19)OCCC1=O

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OC(c7ccccc7)C(C6=O)c(ccc8)c(c89)OC(CC9=O)c1ccccc1

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OCC(C7=O)c(ccc8)c(c89)OC(CC9=O)c1ccccc1

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OC(c8ccccc8)C(C7=O)c(ccc9)c(c19)OCCC1=O

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cc(cc6)Oc(cc7)cc(c78)OC(CC8=O)c9ccccc9

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OC(CC8=O)c9ccccc9

Level: 5

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OCC(C7=O)c(ccc8)c(c89)OCCC9=O

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OCC(C6=O)c(ccc7)c(c78)OC(CC8=O)c9ccccc9

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OC(c7ccccc7)C(C6=O)c(ccc8)c(c89)OCCC9=O

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OCC(C7=O)c(ccc8)c(c89)OCCC9=O

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)COc(c45)cc(cc5)Oc(cc6)cc(c67)OC(CC7=O)c8ccccc8

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cc(cc6)Oc(cc7)cc(c78)OCCC8=O

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OC(CC7=O)c8ccccc8

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)C(c5ccccc5)Oc(c46)cccc6)c(cc3)Oc(cc7)cc(c78)OCCC8=O

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OC(CC7=O)c8ccccc8

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cc(cc5)Oc(cc6)cc(c67)OC(CC7=O)c8ccccc8

Level: 4

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OCC(C6=O)c(ccc7)c(c78)OCCC8=O

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)COc(c45)cc(cc5)Oc(cc6)cc(c67)OCCC7=O

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(C(C4=O)COc(c45)cccc5)c(cc3)Oc(cc6)cc(c67)OCCC7=O

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OC(CC6=O)c7ccccc7

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)c(c(c45)OCCC4=O)c(cc5)Oc(cc6)cc(c67)OCCC7=O

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)COc(c34)cc(cc4)Oc(cc5)cc(c56)OC(CC6=O)c7ccccc7

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cc(cc5)Oc(cc6)cc(c67)OCCC7=O

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)Oc(cc4)cc(c45)OC(CC5=O)c6ccccc6

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCC(C2=O)c(c(c34)OCCC3=O)c(cc4)Oc(cc5)cc(c56)OCCC6=O

Level: 2

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)COc(c34)cc(cc4)Oc(cc5)cc(c56)OCCC6=O

Level: 2

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)Oc(cc4)cc(c45)OCCC5=O

Level: 2

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)cc(cc2)Oc(cc3)cc(c34)OCCC4=O

Level: 1

Mol. Weight: 1130.97 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 1130.97 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 1130.97 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1130.97 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.03
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 124279622.130
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 16241879363.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.060
Plasma Protein Binding: 89.11
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-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: Inhibitor

Excretion

Clearance: 9.550
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -377749333.410
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -155.660
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -29478226202029.531
Rat (Acute): 2.290
Rat (Chronic Oral): 63226.980
Fathead Minnow: 37209981014.960
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 3315483193649.790
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1843064.700
Log(P): -207.67
Log S: -10.08
Log(Vapor Pressure): -109177177254.9
Melting Point: -28739.35
pKa Acid: -795528292.05
pKa Basic: -6399957.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9354
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8661
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8453
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8442
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8347
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8246
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8158
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8148
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8075
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7989
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7610
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7460
Protease	Q5RTL1	Q5RTL1_9HIV1	Human immunodeficiency virus 1	4	0.7397
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7361
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7312
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7309
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7221
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7205
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7041
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7030

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