Acefylline

Details

• Internal ID: 3e29ba21-e914-4c75-b6eb-795ca2b59f1b
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
• IUPAC Name: 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetic acid
• SMILES (Canonical): CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(=O)O
• SMILES (Isomeric): CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(=O)O
• InChI: InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15)
• InChI Key: HCYFGRCYSCXKNQ-UHFFFAOYSA-N
• Popularity: 62 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀N₄O₄
• Molecular Weight: 238.20 g/mol
• Exact Mass: 238.07020481 g/mol
• Topological Polar Surface Area (TPSA): 95.70 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 652-37-9
• Theophylline-7-acetic acid
• Acephylline
• Theophyllineacetic acid
• Carboxymethyltheophylline
• Theophyllin-7-ylacetic acid
• 7-(Carboxymethyl)theophylline
• 7-Theophyllineacetic acid
• 7-Theophyllinylacetic acid
• 7-Theophyllinessigsaeure
• 7-Theophyllinylessigsaeure
• 1,3-Dimethylxanthine-7-acetic acid
• NSC 52996
• (1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid
• 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetic acid
• Purine-7-acetic acid, 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-
• caffeine carboxylic acid
• 2-(1,3-Dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetic acid
• EINECS 211-490-2
• MFCD00022832
• NSC-52996
• Doxophylline metabolite m2
• UNII-M494UE2YEP
• aethaphyllinum
• BRN 0279221
• M494UE2YEP
• 7H-Purine-7-acetic acid, 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-
• Acide theophylline-ethanoique-7 [French]
• CHEMBL70246
• Acide theophylline-ethanoique-7
• DTXSID6057796
• 1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxopurine-7-acetic acid
• ACEFYLLINE PIPERAZINE
• Acepifylline
• Epicophylline
• 2-(1,3-Dimethyl-2,6-Dioxo-2,3,6,7-Tetrahydro-1H-Purin-7-Yl)Acetic Acid
• 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid
• EC 211-490-2
• 2-(p-Chlorphenoxy)-2-methylpropyl 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxopurine-7-acetate
• 5-26-14-00088 (Beilstein Handbook Reference)
• Acefylline piperazine salt
• Piperazine theophylline ethanoate
• acetyloxytheophylline
• Aminodal (Salt/Mix)
• Theophylline-acetic acid
• ACEFYLLINE [MI]
• Acepifylline (Salt/Mix)
• theophylline 7-acetic acid
• ACEFYLLINE [WHO-DD]
• Oprea1_398884
• MLS001032052
• SCHEMBL308514
• LCZC2430
• DTXCID7031585
• CHEBI:94615
• HMS3714E15
• HMS3885C16
• Acefylline sodium salt (Salt/Mix)
• HY-B1505
• NSC52996
• Tox21_113765
• BBL027883
• BDBM50113248
• STK801809
• AKOS000120359
• CAFFEINE CARBOXYLIC ACID [INCI]
• CCG-106578
• CS-7963
• DB13573
• NCGC00253638-01
• CAS-652-37-9
• SMR000718632
• TS-00694
• LS-126434
• FT-0632754
• S3988
• T2941
• EN300-20362
• Theophylline-7-acetic acid, >=99.0% (T)
• A16822
• D82360
• A835035
• AF-684/00246037
• SR-01000898401
• 2-(1,3-dimethyl-2,6-dioxo-7-purinyl)acetic acid
• Q-201818
• Q4673059
• SR-01000898401-2
• F0849-4607
• Z104477882
• Acefylline;Theophyllineacetic acid; Theophylline-7-acetic acid
• Theophilline-7-acetic acid (1,3-Dimethylxantine-7-acetic acid)
• 7H-Purine-7-acetic acid,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-
• Purine-7-acetic acid,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-
• (1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid #
• (1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetic acid
• 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7h-purine-7-acetic acid
• 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXOPURINE-7-ACETIC A
• 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)aceticacid
• 52-37-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9631	96.31%
Caco-2	-	0.7147	71.47%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6338	63.38%
OATP2B1 inhibitior	-	0.8694	86.94%
OATP1B1 inhibitior	+	0.9373	93.73%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9811	98.11%
P-glycoprotein inhibitior	-	0.9297	92.97%
P-glycoprotein substrate	-	0.9108	91.08%
CYP3A4 substrate	-	0.5847	58.47%
CYP2C9 substrate	-	0.5890	58.90%
CYP2D6 substrate	-	0.9024	90.24%
CYP3A4 inhibition	-	0.9871	98.71%
CYP2C9 inhibition	-	0.9629	96.29%
CYP2C19 inhibition	-	0.9468	94.68%
CYP2D6 inhibition	-	0.9645	96.45%
CYP1A2 inhibition	-	0.9613	96.13%
CYP2C8 inhibition	-	0.9290	92.90%
CYP inhibitory promiscuity	-	0.9757	97.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6293	62.93%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9359	93.59%
Skin irritation	-	0.8288	82.88%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6672	66.72%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5842	58.42%
skin sensitisation	-	0.9158	91.58%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7241	72.41%
Acute Oral Toxicity (c)	III	0.7873	78.73%
Estrogen receptor binding	-	0.9016	90.16%
Androgen receptor binding	-	0.7872	78.72%
Thyroid receptor binding	-	0.7960	79.60%
Glucocorticoid receptor binding	-	0.5979	59.79%
Aromatase binding	-	0.6623	66.23%
PPAR gamma	-	0.6082	60.82%
Honey bee toxicity	-	0.9819	98.19%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6305	63.05%
Fish aquatic toxicity	-	0.6784	67.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL255	P29275	Adenosine A2b receptor	27600 nM	Ki	PMID: 12014951

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.96%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.17%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.79%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.17%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.84%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.40%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.15%	99.17%

Plants that contains it

• Pogostemon cablin

Cross-Links

• PubChem: 69550
• NPASS: NPC180493
• ChEMBL: CHEMBL70246
• LOTUS: LTS0131354
• wikiData: Q4673059