Phenylboronic acid

Details

• Internal ID: 4772c5d1-2033-4024-9018-a705af0a76b5
• Taxonomy: Benzenoids > Benzene and substituted derivatives
• IUPAC Name: phenylboronic acid
• SMILES (Canonical): B(C1=CC=CC=C1)(O)O
• SMILES (Isomeric): B(C1=CC=CC=C1)(O)O
• InChI: InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
• InChI Key: HXITXNWTGFUOAU-UHFFFAOYSA-N
• Popularity: 4,683 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₇BO₂
• Molecular Weight: 121.93 g/mol
• Exact Mass: 122.0539096 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.63
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 98-80-6
• Benzeneboronic acid
• Boronic acid, phenyl-
• Phenylboric acid
• Phenylboronicacid
• Dihydroxyphenylborane
• PHENYL BORONIC ACID
• Phenyldihydroxyborane
• Borophenylic acid
• Dihydroxy(phenyl)borane
• USAF BO-2
• Boric acid, phenyl-
• Acide phenylborique
• Kyselina fenylborita
• phenylboranediol
• MFCD00002103
• phenyl-boronic acid
• Phenylboron dihydroxide
• PhB(OH)2
• CHEMBL21485
• CHEBI:44923
• L12H7B02G5
• NSC-66487
• MFCD02093711
• Acide phenylborique [French]
• Kyselina fenylborita [Czech]
• C6H7BO2
• EINECS 202-701-9
• NSC 66487
• BRN 0970972
• UNII-L12H7B02G5
• AI3-18036
• penylboronic acid
• phenyboronic acid
• T-500
• benzenboronic acid
• phenyl boronicacid
• Phenylboronic acid;
• benzene boronic acid
• benzene-boronic acid
• phenyl boronoic acid
• dihydroxy-phenylborane
• dihydroxyphenyl borane
• B-phenyl-boronic acid
• Phenylboronic acid, 22
• WLN: QBQR
• Boronic acid, B-phenyl-
• Phenylboronic acid, 95%
• Ph-B(OH)2
• SCHEMBL4453
• 4-16-00-01654 (Beilstein Handbook Reference)
• C6H5B(OH)2
• BENZENEBORONIC ACID [MI]
• DTXSID9059179
• BDBM26996
• HMS3604B07
• HMS3745G03
• BCP22775
• BCP30011
• NSC66487
• GEO-02109
• AKOS000264727
• AC-1888
• AS-2259
• CS-W001090
• DB01795
• HY-W001090
• OL10071
• NCGC00249450-01
• SY001599
• SY257095
• B-(Phenyl-2,3,4,5,6-d5)boronic acid
• AM20060348
• B0857
• FT-0631515
• 2,3,4,5,6-pentadeuteriumbenzeneboronic acid
• EN300-35190
• Phenyl-d5-boronic acid;Phenylboronic acid-d5
• Phenylboronic acid, purum, >=97.0% (HPLC)
• A845913
• Q408739
• J-802271
• W-100062
• F3146-0086
• Z111782400
• InChI=1/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8370	83.70%
Caco-2	+	0.9284	92.84%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9481	94.81%
OATP1B3 inhibitior	+	0.9474	94.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9206	92.06%
P-glycoprotein inhibitior	-	0.9865	98.65%
P-glycoprotein substrate	-	0.9940	99.40%
CYP3A4 substrate	-	0.8215	82.15%
CYP2C9 substrate	-	0.8238	82.38%
CYP2D6 substrate	-	0.6692	66.92%
CYP3A4 inhibition	-	0.9533	95.33%
CYP2C9 inhibition	-	0.8640	86.40%
CYP2C19 inhibition	-	0.8983	89.83%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	-	0.7978	79.78%
CYP2C8 inhibition	-	0.9272	92.72%
CYP inhibitory promiscuity	-	0.9110	91.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5146	51.46%
Carcinogenicity (trinary)	Non-required	0.5389	53.89%
Eye corrosion	+	0.9231	92.31%
Eye irritation	+	0.9876	98.76%
Skin irritation	+	0.5957	59.57%
Skin corrosion	+	0.6925	69.25%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9162	91.62%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.7177	71.77%
skin sensitisation	+	0.5552	55.52%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5095	50.95%
Acute Oral Toxicity (c)	III	0.6537	65.37%
Estrogen receptor binding	-	0.7453	74.53%
Androgen receptor binding	-	0.8652	86.52%
Thyroid receptor binding	-	0.7497	74.97%
Glucocorticoid receptor binding	-	0.7391	73.91%
Aromatase binding	-	0.8654	86.54%
PPAR gamma	-	0.7515	75.15%
Honey bee toxicity	-	0.9864	98.64%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.6640	66.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.73%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.22%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.17%	94.08%
CHEMBL3902	P09211	Glutathione S-transferase Pi	80.03%	93.81%

Plants that contains it

• Vaccinium macrocarpon

Cross-Links

• PubChem: 66827
• LOTUS: LTS0063398
• wikiData: Q408739