Oxolinic Acid

Details

• Internal ID: 24a7ae3b-efec-4f1c-9cc8-8a6d1da2f93c
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinoline carboxylic acids
• IUPAC Name: 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• InChI: InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
• InChI Key: KYGZCKSPAKDVKC-UHFFFAOYSA-N
• Popularity: 1,418 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₁NO₅
• Molecular Weight: 261.23 g/mol
• Exact Mass: 261.06372245 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 14698-29-4
• Nidantin
• Dioxacin
• Emyrenil
• Utibid
• Prodoxal
• Prodoxol
• Oxolinic
• Oksaren
• Ossian
• Uroxol
• Gramurin
• Starner
• Ultibid
• Oxoboi
• Pietil
• Acido oxolinico
• Acide oxolinique
• Uro-alvar
• Acidum oxolinicum
• Cistopax
• Orthurine
• Tiurasin
• Uritrate
• Urotrate
• Acido ossolico
• NSC-110364
• Aqualinic
• Urinox
• 5-Ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• W 4565
• NSC 110364
• 5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• 1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid
• CCRIS 6301
• HSDB 3243
• 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• EINECS 238-750-8
• UNII-L0A22B22FT
• MFCD00056775
• 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid
• 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid
• BRN 0620635
• Acide oxolinique [INN-French]
• Acido oxolinico [INN-Spanish]
• Acidum oxolinicum [INN-Latin]
• L0A22B22FT
• DTXSID1021089
• CHEBI:138856
• 1,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-
• Oxolinic acid impurity B
• NSC110364
• S-0208
• DTXCID101089
• W-4565
• 1,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-
• NCGC00015762-06
• CAS-14698-29-4
• 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
• 16172-03-5
• OXOLINIC ACID (MART.)
• OXOLINIC ACID [MART.]
• Acide oxolinique (INN-French)
• Acido oxolinico (INN-Spanish)
• Acidum oxolinicum (INN-Latin)
• Acido ossolico [DCIT]
• OXOLINIC ACID (EP MONOGRAPH)
• OXOLINIC ACID [EP MONOGRAPH]
• Acid, Oxolinic
• 5-ETHYL-5,8-DIHYDRO-8-OXO(1,3)DIOXOLO(4,5-G)QUINOLINE-7-CARBOXYLIC ACID
• SR-01000076042
• Inoxyl
• oxolinic-acid
• 5-ethyl-8-oxo-5,8-dihydro(1,3)dioxolo(4,5-g)quinoline-7-carboxylic acid
• Oxolinic acid [USAN:INN:BAN]
• Aqualinic (TN)
• quinolone antibiotic
• Prestwick_629
• Spectrum_001397
• Prestwick0_000193
• Prestwick1_000193
• Prestwick2_000193
• Prestwick3_000193
• Spectrum2_000933
• Spectrum3_001490
• Spectrum4_000073
• Spectrum5_001176
• Lopac-O-0877
• 5,8-Dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
• OXOLINIC ACID [MI]
• Oxolinic acid (USAN/INN)
• OXOLINIC ACID [INN]
• Lopac0_000952
• Oprea1_169598
• SCHEMBL24445
• BSPBio_000145
• BSPBio_003079
• KBioGR_000625
• KBioSS_001877
• OXOLINIC ACID [HSDB]
• OXOLINIC ACID [USAN]
• MLS000028501
• DivK1c_000659
• SPECTRUM1502030
• SPBio_000866
• SPBio_002066
• BPBio1_000161
• CHEMBL416755
• OXOLINIC ACID [WHO-DD]
• HMS502A21
• KBio1_000659
• KBio2_001877
• KBio2_004445
• KBio2_007013
• KBio3_002579
• J01MB05
• NINDS_000659
• HMS1568H07
• HMS1921F12
• HMS2092P09
• HMS2095H07
• HMS3262P06
• HMS3712H07
• Oxolinic acid, analytical standard
• Pharmakon1600-01502030
• Oxolinic acid, quinolone antibiotic
• HY-B1002
• Tox21_110216
• Tox21_202787
• Tox21_500952
• AC8065
• CCG-39666
• NSC758177
• s4537
• 5-ethyl-8-oxo-5-hydro-2H-1,3-dioxoleno[4,5-g]quinoline-7-carboxylic acid
• AKOS000282622
• Tox21_110216_1
• CS-4499
• DB13627
• LP00952
• NSC-758177
• SDCCGSBI-0050926.P004
• IDI1_000659
• NCGC00015762-01
• NCGC00015762-02
• NCGC00015762-03
• NCGC00015762-04
• NCGC00015762-05
• NCGC00015762-07
• NCGC00015762-08
• NCGC00015762-09
• NCGC00015762-10
• NCGC00015762-11
• NCGC00015762-13
• NCGC00015762-17
• NCGC00093361-02
• NCGC00093361-03
• NCGC00093361-04
• NCGC00093361-05
• NCGC00260333-01
• NCGC00261637-01
• AS-12087
• SMR000058314
• SY066716
• SBI-0050926.P003
• EU-0100952
• FT-0637128
• VU0243182-3
• D02301
• O 0877
• WLN: T C566 DO FO JN MV EHJ J2 LVQ
• A808577
• Q287840
• SR-01000076042-1
• SR-01000076042-4
• SR-01000076042-6
• W-108119
• BRD-K73394555-001-08-6
• 5-Ethyl-5,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
• F3351-0487
• 1-Ethyl-1,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid
• Oxolinic acid, European Pharmacopoeia (EP) Reference Standard
• 1,5-g]quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-
• 1.4-Dihydro-1-ethyl-6,7-methylenedioxy-4-oxoquinoline-3-carboxylic acid
• 5-Ethy1-5,8-dihydro-8-oxo-1,3-dioxolo[4,5]quinoline-7-carboxylic acid
• 5-ETHYL-8-OXO-2H,5H,8H-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACID
• 5-Ethyl-8-oxo-5,8-dihydro (1,3) dioxolo (4,5-g) quinoline-7-carboxylic acid
• 5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid #
• W-4565; 5,8-Dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid
• InChI=1/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8924	89.24%
Caco-2	+	0.7124	71.24%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5043	50.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9521	95.21%
OATP1B3 inhibitior	+	0.9466	94.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9567	95.67%
BSEP inhibitior	-	0.8318	83.18%
P-glycoprotein inhibitior	-	0.9327	93.27%
P-glycoprotein substrate	-	0.8247	82.47%
CYP3A4 substrate	-	0.7655	76.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9223	92.23%
CYP3A4 inhibition	-	0.6298	62.98%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9007	90.07%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.8787	87.87%
CYP inhibitory promiscuity	-	0.5784	57.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Warning	0.5191	51.91%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.7348	73.48%
Skin irritation	-	0.8181	81.81%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	+	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9246	92.46%
Micronuclear	+	0.8574	85.74%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5393	53.93%
Acute Oral Toxicity (c)	III	0.7746	77.46%
Estrogen receptor binding	+	0.8242	82.42%
Androgen receptor binding	-	0.7272	72.72%
Thyroid receptor binding	-	0.5940	59.40%
Glucocorticoid receptor binding	-	0.5108	51.08%
Aromatase binding	-	0.6035	60.35%
PPAR gamma	+	0.6358	63.58%
Honey bee toxicity	-	0.9533	95.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.8100	81.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.96%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.71%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.19%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.18%	93.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	91.52%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.17%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.46%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	89.10%	94.42%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.27%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.38%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.27%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.75%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.72%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 4628
• LOTUS: LTS0240921
• wikiData: Q287840