Benzoin
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Basic Info
| Common Name | Benzoin(F05601) |
| 2D Structure | |
| Description | (±)-Benzoin is a flavouring ingredient.Benzoin is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin. (Wikipedia) Benzoin belongs to the family of Benzoins. These are organic compounds containing a 1,2-hydroxy ketone attached to two phenyl groups. |
| FRCD ID | F05601 |
| CAS Number | 119-53-9 |
| PubChem CID | 8400 |
| Formula | C14H12O2 |
| IUPAC Name | 2-hydroxy-1,2-diphenylethanone |
| InChI Key | ISAOCJYIOMOJEB-UHFFFAOYSA-N |
| 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 |
| Canonical SMILES | C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O |
| Isomeric SMILES | C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O |
| Wikipedia | Benzoin |
| Synonyms |
119-53-9
Benzoylphenylcarbinol
BENZOIN
2-Hydroxy-1,2-diphenylethanone
2-Hydroxy-2-phenylacetophenone
Benzoin tincture
Ethanone, 2-hydroxy-1,2-diphenyl-
Bitter almond oil camphor
Phenylbenzoyl carbinol
2-hydroxy-1,2-diphenylethan-1-one
|
| Classifies |
Predicted: Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Stilbenes |
| Subclass | Benzoins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoins |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzoin - Alkyl-phenylketone - Phenylketone - Benzoyl - Aryl ketone - Aryl alkyl ketone - Acyloin - Monocyclic benzene moiety - Benzenoid - Alpha-hydroxy ketone - Secondary alcohol - Ketone - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Aromatic alcohol - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoins. These are organic compounds containing a 1,2-hydroxy ketone attached to two phenyl groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 212.248 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 225 |
| Monoisotopic Mass | 212.084 |
| Exact Mass | 212.084 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9548 |
| Human Intestinal Absorption | HIA+ | 0.9974 |
| Caco-2 Permeability | Caco2+ | 0.9062 |
| P-glycoprotein Substrate | Non-substrate | 0.7764 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8756 |
| Non-inhibitor | 0.8830 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8459 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7218 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7870 |
| CYP450 2D6 Substrate | Non-substrate | 0.9528 |
| CYP450 3A4 Substrate | Non-substrate | 0.7652 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6827 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8224 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9445 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6648 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9508 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7295 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9748 |
| Non-inhibitor | 0.9275 | |
| AMES Toxicity | Non AMES toxic | 0.9577 |
| Carcinogens | Non-carcinogens | 0.6308 |
| Fish Toxicity | High FHMT | 0.7249 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9935 |
| Honey Bee Toxicity | High HBT | 0.6666 |
| Biodegradation | Ready biodegradable | 0.6963 |
| Acute Oral Toxicity | IV | 0.6406 |
| Carcinogenicity (Three-class) | Non-required | 0.7080 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7873 | LogS |
| Caco-2 Permeability | 1.8786 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3583 | LD50, mol/kg |
| Fish Toxicity | 1.8165 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8143 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effects of Litchi chinensis fruit isolates on prostaglandin E(2) and nitric oxide production in J774 murine macrophage cells. | BMC Complement Altern Med | 2012 Mar 1 | 22380404 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]