Halofuginone

Details

• Internal ID: 89a8722c-7155-4d30-9ec8-efb8cb25d108
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinazolines
• IUPAC Name: 7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
• InChI: InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m1/s1
• InChI Key: LVASCWIMLIKXLA-CABCVRRESA-N
• Popularity: 361 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇BrClN₃O₃
• Molecular Weight: 414.70 g/mol
• Exact Mass: 413.01418 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 55837-20-2
• Halofuginonum
• Halocur
• Halofunginone
• L31MM1385E
• Halofuginon
• 7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
• Halofuginone HCl
• 7-bromo-6-chloro-3-{3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl}-3,4-dihydroquinazolin-4-one
• DTXSID0048260
• 7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4-one
• 7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxypiperidin-2-yl)-2-oxopropyl)-3,4-dihydroquinazolin-4-one
• RefChem:783365
• halofuginone monohydrobromide
• 7-bromo-6-chlorofebrifugine
• halofuginone monohydrochloride
• 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone
• DTXCID101769056
• RU19110
• (+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone
• trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone
• 7-bromo-6-chloro-3-(3-(3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4-one
• Halofuginona
• (+)-Halofuginone
• 7-Bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidyl]-2-oxopropyl]-4(3H)-Quinazolinone
• Halofuginone, (+)-
• H84E4Y7HC9
• 6-Chloro-7-bromo-(+)-febrifugine
• (+/-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone
• 868851-54-1
• Halofuginone [INN:BAN]
• C16H17BrClN3O3
• rel-7-Bromo-6-chloro-3-(3-((2R,3S)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one
• 7-Bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone
• 7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidyl]-2-oxo-propyl]quinazolin-4-one
• 7-Bromo-6-Chloro-3-{3-[(2r,3s)-3-Hydroxypiperidin-2-Yl]-2-Oxopropyl}quinazolin-4(3h)-One
• 4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-
• HALOFUGINONE [INN]
• Halofuginonum [INN-Latin]
• Halofuginona [INN-Spanish]
• UNII-L31MM1385E
• HalocurTM
• HT-100
• HFG
• MFCD09834143
• HALOFUGINONE [MI]
• UNII-H84E4Y7HC9
• SCHEMBL9541147
• CHEMBL1199540
• SCHEMBL29396843
• AKOS022185424
• CCG-268823
• DB04866
• (+-)-trans-7-Brom-6-chlor-3-(3-(3-hydroxy-2-piperidyl)acetonyl-4(3H)-chinazolinon
• (+-)-trans-7-Bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)acetonyl-4(3H)-quinazolinone
• trans-7-Bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone
• 4(3H4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, trans-(+/-)-
• HALOFUGINONE [EMA EPAR VETERINARY]
• rel-7-Bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone
• NS00017223
• Q4132745
• BRD-K54247840-004-01-3
• (+/-)-trans-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone hydrobromide
• 4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-((2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, rel-
• 4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, trans-
• 4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, trans-(+-)-
• 4(3H)-QUINAZOLINONE, 7-BROMO-6-CHLORO-3-(3-(3-HYDROXY-2-PIPERIDINYL)-2-OXOPROPYL)-, TRANS-(+/-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9404	94.04%
Caco-2	-	0.8069	80.69%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6479	64.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8958	89.58%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5825	58.25%
P-glycoprotein inhibitior	-	0.7682	76.82%
P-glycoprotein substrate	-	0.5711	57.11%
CYP3A4 substrate	+	0.6323	63.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7723	77.23%
CYP3A4 inhibition	+	0.5591	55.91%
CYP2C9 inhibition	+	0.5325	53.25%
CYP2C19 inhibition	+	0.5863	58.63%
CYP2D6 inhibition	-	0.7765	77.65%
CYP1A2 inhibition	+	0.5391	53.91%
CYP2C8 inhibition	-	0.6089	60.89%
CYP inhibitory promiscuity	+	0.7138	71.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7210	72.10%
Carcinogenicity (trinary)	Non-required	0.5866	58.66%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9901	99.01%
Skin irritation	-	0.7844	78.44%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3967	39.67%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.7157	71.57%
skin sensitisation	-	0.8715	87.15%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6627	66.27%
Acute Oral Toxicity (c)	III	0.6255	62.55%
Estrogen receptor binding	+	0.7386	73.86%
Androgen receptor binding	+	0.5322	53.22%
Thyroid receptor binding	-	0.5902	59.02%
Glucocorticoid receptor binding	+	0.6241	62.41%
Aromatase binding	+	0.6741	67.41%
PPAR gamma	+	0.7034	70.34%
Honey bee toxicity	-	0.9088	90.88%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5949	59.49%
Fish aquatic toxicity	-	0.3626	36.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.32%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.96%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.86%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.28%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.90%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.04%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.30%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.74%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.05%	94.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	86.30%	95.34%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.14%	93.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.10%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	85.97%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.53%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.04%	86.33%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.47%	91.76%
CHEMBL228	P31645	Serotonin transporter	83.00%	95.51%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.22%	90.71%
CHEMBL4789	P35218	Carbonic anhydrase VA	82.20%	96.26%
CHEMBL5957	P21589	5'-nucleotidase	82.04%	97.78%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.89%	90.24%
CHEMBL3384	Q16512	Protein kinase N1	80.10%	80.71%

Plants that contains it

• Hydrangea febrifuga

Cross-Links

• PubChem: 456390
• LOTUS: LTS0242919
• wikiData: Q76118383