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Bruceolline F

Family: Plantae - Simaroubaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)n1cc(c2c1cccc2)C[C@@H](C(O)(C)C)O
InChI	InChI=1S/C19H27NO7/c1-19(2,26)14(22)7-10-8-20(12-6-4-3-5-11(10)12)18-17(25)16(24)15(23)13(9-21)27-18/h3-6,8,13-18,21-26H,7,9H2,1-2H3/t13-,14+,15-,16+,17-,18-/m1/s1
InChIKey	NJNIHOLHKRAEFY-UCIFAOBLSA-N
Formula	C₁₉H₂₇NO₇
HBA	8
HBD	6
MW	381.43
Rotatable Bonds	5
TPSA	135.54
LogP	-0.71
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	381.18
Number of Lipinski Rule Violations	1

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

Showing of synonyms

Makong YS, Fotso GW, et al. (2021). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae).. Natural product research,2021, 35(12), 2037-2043. [View] [PubMed]

Pubchem: 38355088

Zinc: ZINC000031162113

Chebi: 68927

Nmrshiftdb2: 70001210

Metabolights: MTBLC68927

Chembl: CHEMBL1922997

No compound-protein relationship available.

SMILES: c1cccc(c12)n(cc2)C3CCCCO3

Level: 1

Mol. Weight: 381.43 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 381.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 381.43 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -5.56
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.320
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.620
Plasma Protein Binding: 63.36
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.450
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.420
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.830
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.350
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: -9.740
Rat (Acute): 3.140
Rat (Chronic Oral): 3.480
Fathead Minnow: 3.780
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 457.990
Hydration Free Energy: -13.710
Log(D) at pH=7.4: 0.290
Log(P): 0.03
Log S: -2.01
Log(Vapor Pressure): -11.35
Melting Point: 170.66
pKa Acid: 6.56
pKa Basic: 5.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8952
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8866
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8543
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8409
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8359
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8195
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8082
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7956
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7892
Galactoside O-acetyltransferase	P07464	THGA_ECOLI	Escherichia coli	4	0.7835
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7773
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7725
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7700
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7689
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7558
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7532
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7526
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7450
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7435
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7287
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7242
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7179
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7171
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7090
Ribonucleoside-diphosphate reductase large chain 1	P21524	RIR1_YEAST	Saccharomyces cerevisiae	3	0.7085
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7079
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7042
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7023
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7002

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