Orungal

Details

• Internal ID: 46347c4c-da6c-4a95-a6c1-c8874736ffe9
• Taxonomy: Organoheterocyclic compounds > Diazinanes > Piperazines > Phenylpiperazines
• IUPAC Name: 2-butan-2-yl-4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
• SMILES (Canonical): CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
• SMILES (Isomeric): CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@@H]5CO[C@@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
• InChI: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m1/s1
• InChI Key: VHVPQPYKVGDNFY-AVQIMAJZSA-N
• Popularity: 6,757 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
• Molecular Weight: 705.60 g/mol
• Exact Mass: 704.2393071 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.58
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 11

Synonyms

• Itrizole
• Orungal
• Sempera
• Itraconazolum
• Sporonox
• Itraconazol [Spanish]
• Itraconazolum [Latin]
• Triasporin
• Candistat
• Canditral
• Itralek
• Sporamelt
• Traconal
• Itrac
• cis-Itraconazole
• Spherazole CR
• Spherazole IR
• Sporal
• Onmel
• Prokanazol
• Spherazole
• Canadiol
• R 51211
• 84625-61-6
• SUBA Itraconazole
• R-51211
• UNII-304NUG5GF4
• Itrakonazol
• HSDB 7839
• BRN 6042047
• Itraconazole [USAN:USP:INN:BAN:JAN]
• R 51,211
• CHEMBL882
• (+-)-1-sec-Butyl-4-(p-(4-(p-(((2R*,4S*)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-delta(sup 2)-1,2,4-triazolin-5-one
• SCHEMBL301223
• SCHEMBL20464865
• 3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-
• EINECS 283-347-2
• JK-1211
• NSC 759239
• (1)-cis-4-(4-(4-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2,4-dihydro-2-sec-butyl-3H-1,2,4-triazol-3-one
• 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	-	0.8075	80.75%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Mitochondria	0.4776	47.76%
OATP2B1 inhibitior	+	0.6938	69.38%
OATP1B1 inhibitior	+	0.8741	87.41%
OATP1B3 inhibitior	+	0.9196	91.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9883	98.83%
P-glycoprotein inhibitior	+	0.8284	82.84%
P-glycoprotein substrate	+	0.7189	71.89%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	0.7194	71.94%
CYP2D6 substrate	-	0.8080	80.80%
CYP3A4 inhibition	+	0.5279	52.79%
CYP2C9 inhibition	+	0.6180	61.80%
CYP2C19 inhibition	+	0.5703	57.03%
CYP2D6 inhibition	-	0.8622	86.22%
CYP1A2 inhibition	-	0.7666	76.66%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	+	0.8219	82.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7538	75.38%
Carcinogenicity (trinary)	Non-required	0.5194	51.94%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9307	93.07%
Skin irritation	-	0.8147	81.47%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8619	86.19%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	+	0.9321	93.21%
skin sensitisation	-	0.8627	86.27%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7870	78.70%
Acute Oral Toxicity (c)	II	0.7373	73.73%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8446	84.46%
Thyroid receptor binding	+	0.6499	64.99%
Glucocorticoid receptor binding	+	0.7227	72.27%
Aromatase binding	-	0.5855	58.55%
PPAR gamma	-	0.8544	85.44%
Honey bee toxicity	-	0.8605	86.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6482	64.82%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4029	P25024	Interleukin-8 receptor A	100 nM	IC50	via Super-PRED
CHEMBL1790	P30518	Vasopressin V2 receptor	794.33 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2243	O00519	Anandamide amidohydrolase	98.03%	97.53%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.88%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.43%	86.33%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	97.28%	95.34%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.71%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.94%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.47%	98.95%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	94.94%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.72%	94.80%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	94.71%	92.68%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.18%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.67%	96.00%
CHEMBL4208	P20618	Proteasome component C5	91.40%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	90.97%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.92%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.48%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	90.39%	93.65%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	89.82%	92.50%
CHEMBL255	P29275	Adenosine A2b receptor	89.56%	98.59%
CHEMBL5957	P21589	5'-nucleotidase	89.13%	97.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.84%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.90%	92.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.45%	90.24%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.50%	96.67%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	83.16%	92.38%
CHEMBL3691	Q13822	Autotaxin	83.07%	96.39%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.86%	95.78%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.72%	98.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.68%	95.17%
CHEMBL5203	P33316	dUTP pyrophosphatase	82.01%	99.18%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.85%	99.15%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.29%	96.77%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.25%	92.86%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.19%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.13%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.90%	97.14%

Plants that contains it

• Sideritis canariensis
• Sideritis perfoliata subsp. athoa
• Sideritis soluta

Cross-Links

• PubChem: 6917738
• LOTUS: LTS0251506
• wikiData: Q104400456