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Beilschmieflavonoid A

Family: Plantae - Lauraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	COc1c2[C@H](O[C@@H]3C[C@H](Oc4c3c(OC)c(c(c4)OC)OC)c3ccccc3)C[C@H](Oc2cc(c1OC)OC)c1ccccc1
InChI	InChI=1S/C36H38O9/c1-37-29-19-27-31(35(41-5)33(29)39-3)25(17-23(43-27)21-13-9-7-10-14-21)45-26-18-24(22-15-11-8-12-16-22)44-28-20-30(38-2)34(40-4)36(42-6)32(26)28/h7-16,19-20,23-26H,17-18H2,1-6H3/t23-,24-,25+,26+/m0/s1
InChIKey	ATLLKSBDVDILGN-QEGGNFSNSA-N
Formula	C₃₆H₃₈O₉
HBA	9
HBD	0
MW	614.69
Rotatable Bonds	10
TPSA	83.07
LogP	7.58
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	614.25
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Beilschmiedia zenkeri	Lauraceae	Plantae	88849

Showing of synonyms

Lenta BN, Tantangmo F, et al. (2009). Bioactive constituents of the stem bark of Beilschmiedia zenkeri.. Journal of natural products,2009, 72(12), 2130-2134. [View] [PubMed]

Pubchem: 44614521

Cas: 1197826-48-4

Zinc: ZINC000049777645

Nmrshiftdb2: 60054285

Chembl: CHEMBL1075888

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)CC2OC4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 614.69 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)CC2OC4CCOc(c45)cccc5

Level: 2

Mol. Weight: 614.69 g/mol

SMILES: c1cccc(c12)OCCC2OC3CCOc(c34)cccc4

Level: 1

Mol. Weight: 614.69 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 614.69 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 614.69 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 614.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.04
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.19
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 58.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.48
Plasma Protein Binding: 79.38
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 11.45
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.26
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.23
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.42
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -109392.11
Rat (Acute): 3.26
Rat (Chronic Oral): 2.0
Fathead Minnow: 152.33
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 8041.56
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.46
Log(P): 6.06
Log S: -5.64
Log(Vapor Pressure): -277.21
Melting Point: 118.53
pKa Acid: 11.14
pKa Basic: 0.18

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9512
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9165
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.9035
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9012
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8928
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8859
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8480
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8438
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8386
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8321
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8309
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8205
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.8076
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8070
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8025
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7996
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7855
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7842
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7794
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7788
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7753
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7746
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7742
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7710
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7705
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7693
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7645
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7635
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7539
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7526
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7523
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7522
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7508
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7489
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7467
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7438
Protein kinase C iota type	P41743	KPCI_HUMAN	Homo sapiens	4	0.7434
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7400
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7393
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7371
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7371
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7364
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7363
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7358
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7318
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7309
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7306
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7289
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7287
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7286
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7278
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7274
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7259
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7254
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7240
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7232
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7224
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7196
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.7189
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7167
Cell division protein FtsZ	P0A031	FTSZ_STAAU	Staphylococcus aureus	3	0.7164
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7144
Cyclic GMP-AMP synthase	Q8C6L5	CGAS_MOUSE	Mus musculus	3	0.7138
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7132
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7122
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7109
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7108
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7103
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7056
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7056
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7050
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7027
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7023
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7017
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7014
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7011

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