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Bruceanoside A

Family: Plantae - Simaroubaceae
Kingdom: Plantae
Class: Stilbene
- Subclass: Stilbene Glycoside

Canonical Smiles	COc1cc(/C=C/c2ccc(cc2)O[C@@H]2OC(CO[C@H]3OC(C)[C@H]([C@@H](C3O)O)O)[C@H]([C@@H](C2O)O)O)cc(c1)OC
InChI	InChI=1S/C28H36O12/c1-14-21(29)23(31)25(33)27(38-14)37-13-20-22(30)24(32)26(34)28(40-20)39-17-8-6-15(7-9-17)4-5-16-10-18(35-2)12-19(11-16)36-3/h4-12,14,20-34H,13H2,1-3H3/b5-4+/t14?,20?,21-,22-,23+,24+,25?,26?,27+,28-/m1/s1
InChIKey	NFEVXMANPKSNQD-APZQTCFUSA-N
Formula	C₂₈H₃₆O₁₂
HBA	12
HBD	6
MW	564.58
Rotatable Bonds	9
TPSA	176.76
LogP	-0.1
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	564.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Brucea antidysenterica	Simaroubaceae	Plantae	459111

Showing of synonyms

Makong YS, Mouthé Happi G, et al. (2019). Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules, 2019, 24(23), 4412. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=Cc2ccc(cc2)OC(O3)CCCC3COC4CCCCO4

Level: 3

Mol. Weight: 564.58 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 564.58 g/mol

SMILES: c1ccccc1C=Cc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 564.58 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 564.58 g/mol

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 564.58 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 564.58 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.58 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.26
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.890
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.11

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.100
Plasma Protein Binding: 69.34
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.470
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.280
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.610
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.470
Micronucleos: Toxic
NR-AhR: Safe
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: -3669.200
Rat (Acute): 2.590
Rat (Chronic Oral): 3.970
Fathead Minnow: 10.820
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 505.430
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.600
Log(P): 1.22
Log S: -3.56
Log(Vapor Pressure): -11.4
Melting Point: 174.04
pKa Acid: 5.15
pKa Basic: 2.8

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9869
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9739
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9733
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.9099
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8938
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8819
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8815
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8702
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8700
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8586
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8552
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.8437
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8105
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.8044
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8013
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7952
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7936
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7934
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7916
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7799
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7760
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7712
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7707
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7699
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7698
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7685
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7680
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7621
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7603
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7593
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	2	0.7585
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7576
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	3	0.7565
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7560
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	3	0.7556
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7552
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7535
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7527
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7527
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	2	0.7523
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7520
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7495
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	3	0.7491
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7485
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7484
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	2	0.7472
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7467
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7454
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7451
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7448
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7447
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7444
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7442
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7432
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7421
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7412
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7387
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7380
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7374
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7367
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7356
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7351
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7341
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7337
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7333
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	2	0.7330
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7330
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	2	0.7324
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7322
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7317
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7314
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7309
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7308
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7306
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7305
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7300
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7300
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7295
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7295
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7286
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7280
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7265
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7263
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7257
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7246
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7245
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	2	0.7244
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7241
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	2	0.7234
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7216
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7214
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7212
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7211
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7209
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7204
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7203
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7202
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	3	0.7202
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7192
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7190
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7187
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	2	0.7186
UDP-N-acetylglucosamine 1-carboxyvinyltransferase	P33038	MURA_ENTCC	Enterobacter cloacae subsp. cloacae	2	0.7183
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7181
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7180
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7167
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7164
Neprilysin	P08049	NEP_RABIT	Oryctolagus cuniculus	4	0.7161
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7157
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7157
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7156
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7152
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7143
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7133
Protein mono-ADP-ribosyltransferase PARP15	Q460N3	PAR15_HUMAN	Homo sapiens	3	0.7128
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7122
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7111
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	2	0.7110
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7109
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7109
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7107
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7106
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7101
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	2	0.7089
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7084
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7081
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7077
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.7074
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7074
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7073
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7068
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7061
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7052
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7047
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7046
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7042
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7038
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7037
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7037
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7034
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	3	0.7019
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	2	0.7015
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	2	0.7008
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	2	0.7005
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7000

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