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Beilschmieflavonoid B

Family: Plantae - Lauraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	COc1c(OC)cc2c(c1O)[C@@H](C[C@H](O2)c1ccccc1)O[C@@H]1C[C@H](Oc2c1c(OC)c(c(c2)OC)OC)c1ccccc1
InChI	InChI=1S/C35H36O9/c1-37-28-18-25-30(32(36)33(28)39-3)24(16-22(42-25)20-12-8-6-9-13-20)44-26-17-23(21-14-10-7-11-15-21)43-27-19-29(38-2)34(40-4)35(41-5)31(26)27/h6-15,18-19,22-24,26,36H,16-17H2,1-5H3/t22-,23-,24+,26+/m0/s1
InChIKey	DIBGCTMRCXOBNM-HPUZDQILSA-N
Formula	C₃₅H₃₆O₉
HBA	9
HBD	1
MW	600.66
Rotatable Bonds	9
TPSA	94.07
LogP	7.28
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	600.24
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: 44614522

Cas: 1197826-49-5

Zinc: ZINC000049799652

Nmrshiftdb2: 60054286

Chembl: CHEMBL1075889

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 600.66 g/mol

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

Level: 2

Mol. Weight: 600.66 g/mol

SMILES: c1cccc(c12)OCCC2OC3CCOc(c34)cccc4

Level: 1

Mol. Weight: 600.66 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 600.66 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 600.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 600.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.07
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.390
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 34.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.430
Plasma Protein Binding: 84.81
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.060
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.160
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.440
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.460
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: -64551.330
Rat (Acute): 3.100
Rat (Chronic Oral): 2.090
Fathead Minnow: 97.090
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: 2878.870
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.720
Log(P): 5.93
Log S: -5.49
Log(Vapor Pressure): -118.41
Melting Point: 134.89
pKa Acid: 9.6
pKa Basic: 0.32

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9695
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9686
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9540
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9208
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9139
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.9119
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9117
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9090
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9029
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8953
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8946
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8795
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8787
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8768
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8663
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8636
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8629
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8599
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8547
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8389
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8349
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8329
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8247
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8226
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.8167
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8152
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8146
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8141
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8090
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.8065
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8052
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7949
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7944
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7929
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7927
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7912
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7864
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7860
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7845
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7835
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7833
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7815
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7782
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7777
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7755
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7705
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7696
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7674
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7650
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7601
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7600
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7600
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7580
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7573
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7555
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7541
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7503
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7492
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7487
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7483
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7459
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7432
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7421
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7419
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7414
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7389
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7385
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7382
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7356
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7343
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7337
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7324
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7307
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7294
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7293
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7291
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7289
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7286
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7286
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7282
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7275
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7270
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7264
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7254
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	3	0.7253
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7239
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7228
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7225
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7224
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7217
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7216
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7204
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7193
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7182
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7179
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7172
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7169
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	2	0.7158
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7156
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7150
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7148
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7139
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7138
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7133
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7130
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7121
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7111
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7109
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7103
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7095
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7087
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7086
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7081
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7075
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7062
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7058
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7057
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7053
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7052
Inorganic pyrophosphatase	Q3JUV5	Q3JUV5_BURP1	Burkholderia pseudomallei	3	0.7034
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7028
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	3	0.7024
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7007
Metallo-beta-lactamase type 2	P25910	BLAB_BACFG	Bacteroides fragilis	3	0.7004

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