4-Hydroxy-2-butanone

Details

• Internal ID: 0632e1e1-79a8-4276-9159-93bd99b4cbd0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Ketones > Beta-hydroxy ketones
• IUPAC Name: 4-hydroxybutan-2-one
• SMILES (Canonical): CC(=O)CCO
• SMILES (Isomeric): CC(=O)CCO
• InChI: InChI=1S/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3
• InChI Key: LVSQXDHWDCMMRJ-UHFFFAOYSA-N
• Popularity: 619 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11 g/mol
• Exact Mass: 88.052429494 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.04
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 4-Hydroxybutan-2-one
• 590-90-9
• 2-Butanone, 4-hydroxy-
• Methylolacetone
• 3-Oxo-1-butanol
• 3-Oxobutanol
• Monomethylolacetone
• 3-Ketobutan-1-ol
• 4-Butanol-2-one
• 2-Hydroxyethyl methyl ketone
• 4-hydroxy-butan-2-one
• UNII-TCM0BJ44MF
• NSC 41219
• TCM0BJ44MF
• CH3C(O)CH2CH2OH
• EINECS 209-693-6
• MFCD00059005
• NSC-41219
• AI3-11747
• EC 209-693-6
• 68648-26-0
• 3-ketobutanol
• 4H2B compound
• 4-hydroxy butanone
• 1-hydroxy-3-butanone
• 4-oxidanylbutan-2-one
• 1d7j
• 1 -hydroxy-3-butanone
• D04NBE
• ghl.PD_Mitscher_leg0.412
• methyl beta-hydroxyethyl ketone
• 4-Hydroxy-2-butanone, 95%
• DTXSID4060442
• CHEBI:41268
• AMY31061
• NSC41219
• BBL028076
• STL372661
• AKOS009156643
• DB04094
• SB83766
• BUQ
• PD006484
• SY002849
• CS-0044370
• FT-0618625
• H0584
• EN300-84982
• A832151
• A929265
• Q27094939
• Z906206900
• InChI=1/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.8181	81.81%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5970	59.70%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.9502	95.02%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9199	91.99%
P-glycoprotein inhibitior	-	0.9815	98.15%
P-glycoprotein substrate	-	0.9844	98.44%
CYP3A4 substrate	-	0.7668	76.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7863	78.63%
CYP3A4 inhibition	-	0.9621	96.21%
CYP2C9 inhibition	-	0.9565	95.65%
CYP2C19 inhibition	-	0.8862	88.62%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.5785	57.85%
CYP2C8 inhibition	-	0.9950	99.50%
CYP inhibitory promiscuity	-	0.9657	96.57%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5600	56.00%
Carcinogenicity (trinary)	Non-required	0.7624	76.24%
Eye corrosion	+	0.9661	96.61%
Eye irritation	+	0.9942	99.42%
Skin irritation	+	0.8383	83.83%
Skin corrosion	-	0.5719	57.19%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7900	79.00%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	+	0.6130	61.30%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	-	0.9333	93.33%
Reproductive toxicity	-	0.7695	76.95%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.6984	69.84%
Acute Oral Toxicity (c)	III	0.6634	66.34%
Estrogen receptor binding	-	0.9680	96.80%
Androgen receptor binding	-	0.9628	96.28%
Thyroid receptor binding	-	0.9215	92.15%
Glucocorticoid receptor binding	-	0.9443	94.43%
Aromatase binding	-	0.9150	91.50%
PPAR gamma	-	0.9360	93.60%
Honey bee toxicity	-	0.9697	96.97%
Biodegradation	+	0.9250	92.50%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	-	0.9452	94.52%

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	92.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.38%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.51%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	81.28%	83.82%

Plants that contains it

• Glycyrrhiza glabra

Cross-Links

• PubChem: 111509
• NPASS: NPC274925
• LOTUS: LTS0225713
• wikiData: Q27094939