Chelidonic acid

Details

• Internal ID: 77c9b7c7-6a08-4650-9935-32ef82ee6591
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: 4-oxopyran-2,6-dicarboxylic acid
• SMILES (Canonical): C1=C(OC(=CC1=O)C(=O)O)C(=O)O
• SMILES (Isomeric): C1=C(OC(=CC1=O)C(=O)O)C(=O)O
• InChI: InChI=1S/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)
• InChI Key: PBAYDYUZOSNJGU-UHFFFAOYSA-N
• Popularity: 190 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₄O₆
• Molecular Weight: 184.10 g/mol
• Exact Mass: 184.00078784 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 99-32-1
• 4-OXO-4H-PYRAN-2,6-DICARBOXYLIC ACID
• Jervaic acid
• Jerva acid
• Jervasic acid
• Compound XI*
• 4-oxopyran-2,6-dicarboxylic acid
• 2,6-Dicarboxyl-4-pyrone
• 4H-Pyran-2,6-dicarboxylic acid, 4-oxo-
• NSC 3979
• Compound XI* (Cherry and Hageman)
• 4-Oxo-1,4-pyran-2,6-dicarboxylic acid
• gamma-Pyrone-2,6-dicarboxylic acid
• EINECS 202-749-0
• UNII-T33U4W5K6O
• BRN 0163607
• C7H4O6
• T33U4W5K6O
• AI3-19253
• NSC-3979
• .gamma.-Pyrone-2,6-dicarboxylic acid
• DTXSID30243928
• NSC3979
• 5-18-08-00646 (Beilstein Handbook Reference)
• chelidonsaure
• MFCD00006577
• 4-Oxo-4H-pyran-2,6-dicarboxylicacid
• Chelidonic acid, 98%
• 2,6-dicarboxy-4-pyrone
• 4H-Pyran-2, 4-oxo-
• TimTec1_001281
• SCHEMBL70569
• CHELIDONIC ACID [MI]
• 4-Oxo-1,6-dicarboxylic acid
• WLN: T6O DVJ BVQ FVQ
• CHEBI:3586
• Chelidonic acid (not validated)
• y-Pyrone-2,6-dicarboxylic acid
• PBAYDYUZOSNJGU-UHFFFAOYSA-
• DTXCID60166419
• HMS1537K05
• HMS3886K12
• 4-oxo-pyran-2,6-dicarboxylic acid
• AMY36600
• C7-H4-O6
• Chelidonic acid, analytical standard
• 4-oxo-4H-pyran-2,6-dicarboxylsyre
• BBL037230
• c0955
• s5579
• STK735535
• AKOS003368630
• CCG-266462
• CS-W022229
• DS-1596
• HY-W041489
• NCGC00174597-01
• BP-12076
• LS-127299
• BB 0221249
• FT-0623586
• EN300-82795
• A19372
• C08476
• AR-360/40172582
• Q908483
• Chelidonic acid, purum, anhydrous, >=98.0% (T)
• Z1238543360
• HLD
• InChI=1/C7H4O6/c8-3-1-4(6(9)10)13-5(2-3)7(11)12/h1-2H,(H,9,10)(H,11,12)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8331	83.31%
Caco-2	-	0.7942	79.42%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8002	80.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9558	95.58%
OATP1B3 inhibitior	+	0.9661	96.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9834	98.34%
P-glycoprotein inhibitior	-	0.9689	96.89%
P-glycoprotein substrate	-	0.9945	99.45%
CYP3A4 substrate	-	0.8103	81.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9045	90.45%
CYP3A4 inhibition	-	0.9068	90.68%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9620	96.20%
CYP2D6 inhibition	-	0.9696	96.96%
CYP1A2 inhibition	-	0.9706	97.06%
CYP2C8 inhibition	-	0.9761	97.61%
CYP inhibitory promiscuity	-	0.9723	97.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8434	84.34%
Carcinogenicity (trinary)	Non-required	0.6635	66.35%
Eye corrosion	-	0.7900	79.00%
Eye irritation	+	0.9961	99.61%
Skin irritation	+	0.7344	73.44%
Skin corrosion	-	0.8354	83.54%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9142	91.42%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8416	84.16%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.6083	60.83%
Acute Oral Toxicity (c)	III	0.5236	52.36%
Estrogen receptor binding	-	0.9032	90.32%
Androgen receptor binding	-	0.6935	69.35%
Thyroid receptor binding	-	0.8809	88.09%
Glucocorticoid receptor binding	+	0.6059	60.59%
Aromatase binding	-	0.8223	82.23%
PPAR gamma	-	0.6389	63.89%
Honey bee toxicity	-	0.9359	93.59%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.3880	38.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.76%	87.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.77%	91.11%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.46%	81.11%
CHEMBL4040	P28482	MAP kinase ERK2	86.16%	83.82%
CHEMBL2581	P07339	Cathepsin D	84.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.76%	94.42%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.59%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.17%	99.17%

Plants that contains it

• Asparagus officinalis
• Chelidonium majus
• Convallaria keiskei
• Leucojum aestivum
• Stylophorum diphyllum
• Zea mays

Cross-Links

• PubChem: 7431
• NPASS: NPC154592
• LOTUS: LTS0084071
• wikiData: Q908483