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Lemairone B

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](CC2=O)c1ccc(c(c1)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](CC2=O)c1ccc(c(c1)O)O
InChI	InChI=1S/C60H42O21/c61-27-7-1-23(2-8-27)57-53(51-38(71)19-37(70)47-39(72)20-42(78-59(47)51)25-5-11-31(64)33(66)13-25)55(75)50-36(69)17-30(18-45(50)81-57)77-46-22-41(74)48-40(73)21-43(26-6-12-32(65)34(67)14-26)79-60(48)52(46)54-56(76)49-35(68)15-29(63)16-44(49)80-58(54)24-3-9-28(62)10-4-24/h1-19,22,42-43,53-54,57-58,61-71,74H,20-21H2/t42-,43+,53-,54+,57+,58-/m1/s1
InChIKey	RXCYSILOGDSFAY-KAMZHJCZSA-N
Formula	C₆₀H₄₂O₂₁
HBA	21
HBD	12
MW	1098.98
Rotatable Bonds	8
TPSA	357.19
LogP	9.56
Number Rings	12
Number Aromatic Rings	8
Heavy Atom Count	81
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	1098.22
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: 132556532

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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 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: 1098.98 g/mol

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

Level: 3

Mol. Weight: 1098.98 g/mol

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

Level: 3

Mol. Weight: 1098.98 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: 1098.98 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: 1098.98 g/mol

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

Level: 2

Mol. Weight: 1098.98 g/mol

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

Level: 2

Mol. Weight: 1098.98 g/mol

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

Level: 2

Mol. Weight: 1098.98 g/mol

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

Level: 1

Mol. Weight: 1098.98 g/mol

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

Level: 1

Mol. Weight: 1098.98 g/mol

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

Level: 1

Mol. Weight: 1098.98 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 1098.98 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1098.98 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -5.89
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 34539130.560
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 4513860670.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.210
Plasma Protein Binding: 94.77
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: Non-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: 9.660
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -104982177.690
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -44.780
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: -8192439355308.390
Rat (Acute): 2.200
Rat (Chronic Oral): 17571.070
Fathead Minnow: 10341216741.360
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: 921422381572.260
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -512203.800
Log(P): -51.33
Log S: -10.68
Log(Vapor Pressure): -30341970908.21
Melting Point: -5684.51
pKa Acid: -221089004.28
pKa Basic: -1778608.71

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	0.9473
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8928
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8808
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8697
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8521
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8339
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8323
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8188
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8184
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8106
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8090
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	4	0.7935
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7904
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7797
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7769
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7726
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7722
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7721
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7720
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7664
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7642
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7608
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	5	0.7604
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7604
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7563
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	4	0.7550
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7549
Primosomal protein N'	A6TGC5	A6TGC5_KLEP7	Klebsiella pneumoniae subsp. pneumoniae	4	0.7544
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7541
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7540
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7494
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7468
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7445
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7418
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7404
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7400
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7383
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7335
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7308
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7295
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7250
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7245
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7230
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7227
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7206
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7201
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7185
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7175
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7170
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.7169
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7143
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7103
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7100
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7077
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7070
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7056
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7048
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7029
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7024

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