Benzoin

Details

• Internal ID: f3321307-46fe-4fc6-9fb1-fc2bbf4159ac
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Benzoins
• IUPAC Name: 2-hydroxy-1,2-diphenylethanone
• SMILES (Canonical): C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O
• InChI: InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
• InChI Key: ISAOCJYIOMOJEB-UHFFFAOYSA-N
• Popularity: 2,767 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24 g/mol
• Exact Mass: 212.083729621 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 119-53-9
• 2-Hydroxy-1,2-diphenylethanone
• 2-Hydroxy-2-phenylacetophenone
• Benzoylphenylcarbinol
• DL-BENZOIN
• 579-44-2
• Ethanone, 2-hydroxy-1,2-diphenyl-
• alpha-Hydroxybenzyl phenyl ketone
• Phenylbenzoyl carbinol
• (+-)-Benzoin
• 2-hydroxy-1,2-diphenylethan-1-one
• alpha-Hydroxy-alpha-phenylacetophenone
• Aerozoin
• Phenyl-alpha-hydroxybenzyl ketone
• desyl alcohol
• FEMA No. 2132
• NCI-C50011
• Acetophenone, 2-hydroxy-2-phenyl-
• NSC 8082
• CCRIS 75
• Wy 42956
• (RS)-Benzoin
• Hydroxy-2-phenyl acetophenone
• Benzoin (VAN)
• CCRIS 6696
• HSDB 384
• 2-hydroxy-1,2-diphenyl-ethanone
• Ketone, alpha-hydroxybenzyl phenyl
• 2-hydroxy-1,2-di(phenyl)ethanone
• NSC-8082
• EINECS 204-331-3
• EINECS 209-441-5
• Fenyl-alpha-hydroxybenzylketon [Czech]
• BRN 0391839
• UNII-L7J6A1NE81
• a-Hydroxybenzyl phenyl ketone
• Fenyl-alpha-hydroxybenzylketon
• WY-42956
• AI3-00851
• CCRIS 9123
• CHEMBL190677
• L7J6A1NE81
• 9000-72-0
• DTXSID1020144
• CHEBI:17682
• 2-hydroxy-1,2-diphenyl ethanone
• Alpha-hydroxy-a-phenylacetophenone
• Phenyl-.alpha.-hydroxybenzyl ketone
• Ketone, .alpha.-hydroxybenzyl phenyl
• NCGC00091396-02
• (1)-2-Hydroxy-1,2-diphenylethan-1-one
• .alpha.-Hydroxy-.alpha.-phenylacetophenone
• EC 204-331-3
• Ethanone, 2-hydroxy-1,2-diphenyl-, (A+/-)-
• 4-08-00-01279 (Beilstein Handbook Reference)
• DTXCID10144
• CAS-119-53-9
• 56830-64-9
• MFCD00004496
• benzoine
• Benzoin absolute
• DL-Benzoin; Desyl alcohol;(+/-)-2-Hydroxy-2-phenylacetophenone
• PhCH(OH)COPh
• PhCOCH(OH)Ph
• Benzoin, 98%
• (+/-)-benzoin
• Benzoin, >=98%
• BENZOIN [MI]
• (.+/-.)-Benzoin
• WLN: QYR&VR
• SCHEMBL145
• D0Z5KQ
• Hyperabsolute benzoin, Siam
• Benzoin, analytical standard
• Oprea1_687165
• MLS002152893
• a-Hydroxy-a-phenylacetophenone
• FEMA No. 2133
• hydroxy-2-pheny l acetophenone
• BENZOIN, (+/-)
• 2-hydroxy-2-phenyl-acetophenone
• BENZOIN, (+/-)-
• Fenyl-.alpha.-hydroxybenzylketon
• BDBM22728
• FEMA 2132
• HSDB 1929
• NSC8082
• alpha -Hydroxybenzyl phenyl ketone
• HMS3039I03
• Phenyl-alpha -hydroxybenzyl ketone
• Etanona, 2-hidroxi-1,2-difenil-
• .alpha.-Hydroxybenzyl phenyl ketone
• HY-B1550
• Tox21_111126
• Tox21_201888
• Tox21_302790
• STK358785
• AKOS000118894
• AKOS016038141
• Tox21_111126_1
• 2-Hydroxy-1,2-diphenylethanone, 9CI
• Benzoin 100 microg/mL in Acetonitrile
• CS-W020562
• DB14020
• alpha -Hydroxy-alpha -phenylacetophenone
• NCGC00091396-01
• NCGC00091396-03
• NCGC00091396-05
• NCGC00256433-01
• NCGC00259437-01
• AC-11139
• Benzoin, Vetec(TM) reagent grade, 98%
• BS-14748
• SMR001224505
• (+-)-2-hydroxy-1,2-diphenylethan-1-one
• LS-163970
• B0079
• B0222
• Benzoin Zone Refined (number of passes:40)
• Benzoin, purified by sublimation, >=99.5%
• FT-0612530
• FT-0626841
• FT-0635908
• FT-0635909
• EN300-18095
• C01408
• D77908
• (+/-)-2-HYDROXY-1,2-DIPHENYLETHANONE
• A804309
• AE-848/06163047
• Ethanone, 2-hydroxy-1,2-diphenyl-, (.+/-.)-
• Q426819
• SR-01000854680
• J-004149
• J-509605
• SR-01000854680-2
• Z57160197
• F0001-0307
• DL-Benzoin; Desyl alcohol;()-2-Hydroxy-2-phenylacetophenone
• Ethanone, 2-hydroxy-1,2-diphenyl-, mixt. with aloe, storax and Tolu Balsam, tincture

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.9012	90.12%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7218	72.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9695	96.95%
OATP1B3 inhibitior	+	0.9234	92.34%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6993	69.93%
P-glycoprotein inhibitior	-	0.9602	96.02%
P-glycoprotein substrate	-	0.9859	98.59%
CYP3A4 substrate	-	0.7900	79.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7418	74.18%
CYP3A4 inhibition	-	0.9508	95.08%
CYP2C9 inhibition	-	0.8224	82.24%
CYP2C19 inhibition	-	0.6648	66.48%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	+	0.6827	68.27%
CYP2C8 inhibition	-	0.9756	97.56%
CYP inhibitory promiscuity	-	0.7295	72.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.5400	54.00%
Carcinogenicity (trinary)	Non-required	0.7080	70.80%
Eye corrosion	-	0.8487	84.87%
Eye irritation	+	0.9668	96.68%
Skin irritation	+	0.7895	78.95%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8452	84.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	+	0.9013	90.13%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.8111	81.11%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.7595	75.95%
Acute Oral Toxicity (c)	IV	0.6406	64.06%
Estrogen receptor binding	-	0.7010	70.10%
Androgen receptor binding	-	0.6333	63.33%
Thyroid receptor binding	-	0.5303	53.03%
Glucocorticoid receptor binding	-	0.5700	57.00%
Aromatase binding	+	0.7270	72.70%
PPAR gamma	+	0.7795	77.95%
Honey bee toxicity	-	0.9483	94.83%
Biodegradation	+	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8297	82.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	7250 nM; 7250 nM	Ki; Ki	PMID: 15828829; PMID: 16107154
CHEMBL3180	O00748	Carboxylesterase 2	2220 nM; 2220 nM	Ki; Ki	PMID: 15828829; PMID: 16107154
CHEMBL1293235	P02545	Prelamin-A/C	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	92.76%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.78%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.06%	94.62%
CHEMBL2581	P07339	Cathepsin D	87.90%	98.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.58%	100.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.53%	93.81%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.48%	94.08%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	86.45%	98.33%
CHEMBL2535	P11166	Glucose transporter	86.35%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.50%	86.33%
CHEMBL4267	P37173	TGF-beta receptor type II	81.44%	88.18%

Plants that contains it

• Sorghum bicolor

Cross-Links

• PubChem: 8400
• NPASS: NPC249067
• ChEMBL: CHEMBL190677