Etofylline

Details

• Internal ID: 1ee73363-48df-4d81-9196-5b067e90c965
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
• IUPAC Name: 7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione
• SMILES (Canonical): CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCO
• SMILES (Isomeric): CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCO
• InChI: InChI=1S/C9H12N4O3/c1-11-7-6(8(15)12(2)9(11)16)13(3-4-14)5-10-7/h5,14H,3-4H2,1-2H3
• InChI Key: NWPRCRWQMGIBOT-UHFFFAOYSA-N
• Popularity: 201 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂N₄O₃
• Molecular Weight: 224.22 g/mol
• Exact Mass: 224.09094026 g/mol
• Topological Polar Surface Area (TPSA): 78.70 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.57
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 519-37-9
• 7-(2-Hydroxyethyl)theophylline
• Aethophyllinum
• Oxyphylline
• Cordalin
• Frekaphyllin
• Soluphylline
• Phyllocormin N
• Ascorphylline
• Dilaphyllin
• Oxytheonyl
• Oxyethyltheophylline
• Sklerodormal
• Bio-phylline
• Corophyllin-N
• Oxphylline (amido)
• 1,3-Dimethyl-7-(2-hydroxyethyl)xanthine
• 7-Theophyllineethanol
• 7-hydroxyethyltheophylline
• Oxyetophyllinum
• Oxyphyllin
• 7-(Hydroxyethyl)theophylline
• Hydroxyethyl theophylline
• Theophylline, 7-(2-hydroxyethyl)-
• 7-(2-Hydroxyethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
• Oxyaethyltheophyllin
• Etofillina [DCIT]
• etophylline
• Hydroxyethyltheophylline
• Etofillina
• Etofyllinum
• Oxphylline
• Etofilina
• Etofylline [INN:BAN]
• Etofilina [INN-Spanish]
• Etofyllinum [INN-Latin]
• 7-(2-Hydroxyethyl)-1,3-dimethylxanthine
• Oxyaethyltheophyllin [German]
• NSC 113373
• 7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione
• C9H12N4O3
• BETA-HYDROXYETHYL THEOPHYLLINE
• EINECS 208-269-8
• Doxophylline metabolite m4
• 7-(2-Hydroxyethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione
• CHEMBL699
• NSC-113373
• 1H-Purine-2,6-dione, 3,7-dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-
• 3,7-Dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-1H-purine-2,6-dione
• BRN 0251760
• etophyllin
• oxyethophylline
• UNII-L164909TBI
• MLS000115542
• DTXSID5023031
• 7-(2'-Hydroxyethyl)theophylline
• KT-200G
• L164909TBI
• Etofylline (INN)
• 7-(.beta.-Hydroxyethyl)theophylline
• 7-(2-hydroxyethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• NCGC00016479-06
• CAS-519-37-9
• SMR000058179
• ETOFYLLINE [INN]
• 5-26-14-00038 (Beilstein Handbook Reference)
• DTXCID603031
• Oxyphyllin (TN)
• Prestwick_210
• MFCD00055055
• Spectrum_000319
• 7-(beta-HYDROXYETHYL)-THEOPHYLLINE
• ETOFYLLINE [MI]
• Opera_ID_628
• Etofylline [BAN:INN]
• Prestwick0_000172
• Prestwick1_000172
• Prestwick2_000172
• Prestwick3_000172
• Spectrum2_001819
• Spectrum3_001711
• Spectrum4_000179
• Spectrum5_001332
• ChemDiv2_005108
• D0PB2W
• Cambridge id 6649214
• ETOFYLLINE [MART.]
• ETOFYLLINE [WHO-DD]
• BSPBio_000063
• BSPBio_003322
• KBioGR_000697
• KBioSS_000799
• MLS000069731
• BIDD:GT0586
• DivK1c_000052
• SCHEMBL149271
• SPECTRUM2300357
• SPBio_001837
• SPBio_001984
• 7-(b-Hydroxyethyl)theophylline
• BPBio1_000071
• ETOFYLLINE [EP IMPURITY]
• 7-(2-hydroxyethyl)theo-phylline
• BCBcMAP01_000126
• CHEBI:94764
• HMS500C14
• KBio1_000052
• KBio2_000799
• KBio2_003367
• KBio2_005935
• KBio3_002542
• NINDS_000052
• HMS1383I04
• HMS1568D05
• HMS2095D05
• HMS2235K09
• HMS3370P21
• HMS3712D05
• Etofylline 1.0 mg/ml in Methanol
• HY-B1209
• Tox21_110447
• BDBM50025585
• CCG-39731
• NSC113373
• s5029
• STK970528
• 7-( beta -Hydroxyethyl)-theophylline
• AKOS000121416
• Tox21_110447_1
• CS-4837
• CS-O-11645
• GS-6113
• IDI1_000052
• IDI1_003823
• SMP1_000162
• 7-(beta-Hydroxyethyl)theophylline, solid
• NCGC00016479-01
• NCGC00016479-02
• NCGC00016479-03
• NCGC00016479-04
• NCGC00016479-05
• NCGC00016479-07
• NCGC00016479-08
• NCGC00016479-09
• NCGC00016479-11
• NCGC00022341-03
• NCGC00022341-04
• NCGC00178140-01
• NCGC00178140-02
• LS-149582
• AB00052458
• FT-0668429
• THEOPHYLLINE IMPURITY F [EP IMPURITY]
• WLN: T56 BN DN FNVNVJ B2Q F1 H1
• DIPROPHYLLINE IMPURITY C [EP IMPURITY]
• EN300-21180
• D07933
• H10495
• A828855
• SR-01000000166
• 7-(2-hydroxyethyl)-1,3-dimethyl-purine-2,6-dione
• Q3733837
• SR-01000000166-3
• W-109548
• BRD-K83064458-001-05-7
• THEOPHYLLINE MONOHYDRATE IMPURITY F [EP IMPURITY]
• Z104493598
• Etofylline, European Pharmacopoeia (EP) Reference Standard
• 1H-Purine-2, 3,7-dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-
• 7-(2-Hydroxy-ethyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione
• 3,7-dihydro-7-(2-hydroxyethyl)- 1,3-dimethyl-1H-purine-2,6-dione
• 7-(2-Hydroxyethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	-	0.6939	69.39%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7532	75.32%
OATP2B1 inhibitior	-	0.8684	86.84%
OATP1B1 inhibitior	+	0.9256	92.56%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9791	97.91%
P-glycoprotein inhibitior	-	0.8973	89.73%
P-glycoprotein substrate	-	0.8968	89.68%
CYP3A4 substrate	-	0.5700	57.00%
CYP2C9 substrate	-	0.5764	57.64%
CYP2D6 substrate	-	0.8678	86.78%
CYP3A4 inhibition	-	0.9439	94.39%
CYP2C9 inhibition	-	0.9637	96.37%
CYP2C19 inhibition	-	0.9372	93.72%
CYP2D6 inhibition	-	0.9644	96.44%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9621	96.21%
CYP inhibitory promiscuity	-	0.9393	93.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6578	65.78%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9812	98.12%
Skin irritation	-	0.8248	82.48%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3743	37.43%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.9123	91.23%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4758	47.58%
Acute Oral Toxicity (c)	III	0.7757	77.57%
Estrogen receptor binding	-	0.8681	86.81%
Androgen receptor binding	-	0.7360	73.60%
Thyroid receptor binding	-	0.6867	68.67%
Glucocorticoid receptor binding	-	0.6837	68.37%
Aromatase binding	-	0.7542	75.42%
PPAR gamma	-	0.7447	74.47%
Honey bee toxicity	-	0.9710	97.10%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6320	63.20%
Fish aquatic toxicity	-	0.9451	94.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL255	P29275	Adenosine A2b receptor	17300 nM; 17300 nM	Ki; Ki	PMID: 12014951; PMID: 20537438
CHEMBL1293235	P02545	Prelamin-A/C	3162.3 nM; 2238.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.91%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.83%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.93%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.66%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.85%	89.34%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.80%	94.42%

Plants that contains it

• Conioselinum anthriscoides
• Ligusticum officinale

Cross-Links

• PubChem: 1892
• NPASS: NPC109322
• ChEMBL: CHEMBL699