Acetoacetic Acid

Details

• Internal ID: a00c8011-337d-48e5-854e-e2e2691eaa3e
• Taxonomy: Organic acids and derivatives > Keto acids and derivatives > Short-chain keto acids and derivatives
• IUPAC Name: 3-oxobutanoic acid
• InChI: InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
• InChI Key: WDJHALXBUFZDSR-UHFFFAOYSA-N
• Popularity: 3,667 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09 g/mol
• Exact Mass: 102.031694049 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3-oxobutanoic acid
• 541-50-4
• 3-oxobutyric acid
• acetoacetate
• 3-ketobutyrate
• beta-ketobutyric acid
• diacetic acid
• Butanoic acid, 3-oxo-
• oxobutyrate
• 3-Ketobutyric acid
• 3-oxo-butanoic acid
• diacetate
• acetylacetic acid
• 3-OXO-BUTYRIC ACID
• UNII-4ZI204Y1MC
• 3-ketobutanoic acid
• 4ZI204Y1MC
• CHEBI:15344
• 4387-93-3
• DTXSID00202441
• 3-oxobutanate
• 3-oxobutanoicacid
• AAE
• 3-Oxobutyrate
• lithium-acetoacetate
• acetonecarboxylic acid
• SCHEMBL6620
• .ALPHA.-KETOBUTYRATE
• ACETOACETIC ACID [MI]
• CHEMBL1230762
• SCHEMBL13341499
• DTXCID00124932
• WDJHALXBUFZDSR-UHFFFAOYSA-N
• LMFA01060003
• AKOS006241271
• AM85395
• DB01762
• HY-112540
• CS-0046333
• C00164
• EN300-106488
• Q409692
• A6DBA337-E696-4022-A9F9-1757E3CDBFAE
• QuadraPure(R) AK, 50-90 mesh, extent of labeling: 2.0-3.0 mmol/g loading, 1 % cross-linked with divinylbenzene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9687	96.87%
Caco-2	+	0.5161	51.61%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8149	81.49%
OATP2B1 inhibitior	-	0.8648	86.48%
OATP1B1 inhibitior	+	0.9676	96.76%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9571	95.71%
P-glycoprotein inhibitior	-	0.9838	98.38%
P-glycoprotein substrate	-	0.9766	97.66%
CYP3A4 substrate	-	0.7945	79.45%
CYP2C9 substrate	-	0.5733	57.33%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.9731	97.31%
CYP2C9 inhibition	-	0.9777	97.77%
CYP2C19 inhibition	-	0.9582	95.82%
CYP2D6 inhibition	-	0.9614	96.14%
CYP1A2 inhibition	-	0.9394	93.94%
CYP2C8 inhibition	-	0.9970	99.70%
CYP inhibitory promiscuity	-	0.9924	99.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5354	53.54%
Carcinogenicity (trinary)	Non-required	0.7165	71.65%
Eye corrosion	+	0.9899	98.99%
Eye irritation	+	0.9933	99.33%
Skin irritation	+	0.8078	80.78%
Skin corrosion	+	0.9763	97.63%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8264	82.64%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8856	88.56%
Respiratory toxicity	-	0.9444	94.44%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	+	0.4944	49.44%
Acute Oral Toxicity (c)	III	0.8370	83.70%
Estrogen receptor binding	-	0.9740	97.40%
Androgen receptor binding	-	0.9617	96.17%
Thyroid receptor binding	-	0.9037	90.37%
Glucocorticoid receptor binding	-	0.9448	94.48%
Aromatase binding	-	0.9366	93.66%
PPAR gamma	-	0.8763	87.63%
Honey bee toxicity	-	0.9822	98.22%
Biodegradation	+	0.9500	95.00%
Crustacea aquatic toxicity	-	0.9700	97.00%
Fish aquatic toxicity	-	0.6805	68.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.26%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.24%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.48%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	80.45%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.31%	99.17%

Plants that contains it

• Pseudostellaria heterophylla

Cross-Links

• PubChem: 96
• LOTUS: LTS0221314
• wikiData: Q409692