[(2S)-3-hydroxy-2-phenylpropyl] carbamate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for [(2S)-3-hydroxy-2-phenylpropyl] carbamate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the [(2S)-3-hydroxy-2-phenylpropyl] carbamate?

The molecule [(2S)-3-hydroxy-2-phenylpropyl] carbamate presents a molecular formula of C10H13NO3 and its IUPAC name is [(2S)-3-hydroxy-2-phenylpropyl] carbamate.

Carbamate molecules are found in a variety of drugs and pesticides. They are also found in some natural products, such as the amino acids glycine and beta-alanine. Carbamate molecules can be divided into two main groups: those with one carbon atom between the carbonyl group and the amine group (primary carbamates), and those with two carbon atoms between the carbonyl group and the amine group (secondary carbamates). The carbamate [(2S)-3-hydroxy-2-phenylpropyl] is a primary carbamate..

Carbamates are used as pesticides because they are effective at killing a wide variety of pests, including insects, spiders, mites, and nematodes. Carbamates are also used as herbicides, insecticides, and fungicides. Some carbamates are used as drugs to treat conditions such as Alzheimer's disease, Parkinson's disease, and epilepsy..

The mode of action of carbamates is similar to that of organophosphates. Carbamates bind to the active site of an enzyme called acetylcholinesterase. This enzyme is responsible for breaking down acetylcholine, a neurotransmitter. When carbamates bind to the enzyme, they inhibit its activity, leading to an accumulation of acetylcholine. This excess of acetylcholine causes a variety of symptoms, including muscle weakness, paralysis, and death..

The toxicity of carbamates varies depending on the compound. Some carbamates, such as aldicarb and carbaryl, are highly toxic to humans. Others, such as iprovalicarb and propoxur, are less toxic. The LD50, or lethal dose for 50% of the population, of a carbamate is the measure of its toxicity..

Carbamates are absorbed through the skin, lungs, and gastrointestinal tract. They are then metabolized in the liver and excreted in the urine..

Carbamates are considered to be moderately toxic to humans. Symptoms of carbamate poisoning include headache, dizziness, nausea, vomiting, sweating, blurred vision, and muscle weakness. Severe poisoning can lead to seizures, coma, and death..

There is no specific antidote for carbamate poisoning. Treatment focuses on supportive care and removal of the carbamate from the body..

Carbamates are found in a variety of products, including pesticides, herbicides, insecticides, and drugs. Some carbamates are highly toxic to humans, while others are less toxic. Carbamates are absorbed through the skin, lungs, and gastrointestinal tract and are then metabolized in the liver and excreted in the urine. There is no specific antidote for carbamate poisoning, and treatment focuses on supportive care and removal of the carbamate from the body..

3D structure

Cartesian coordinates

Geometry of [(2S)-3-hydroxy-2-phenylpropyl] carbamate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

[(2S)-3-hydroxy-2-phenylpropyl] carbamate JQVQIZWJBLGVRW-VIFPVBQESA-N chemical compound 2D structure molecule svg
[(2S)-3-hydroxy-2-phenylpropyl] carbamate

 

Molecule descriptors

 
IUPAC name[(2S)-3-hydroxy-2-phenylpropyl] carbamate
InChI codeInChI=1S/C10H13NO3/c11-10(13)14-7-9(6-12)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H2,11,13)/t9-/m0/s1
InChI KeyJQVQIZWJBLGVRW-VIFPVBQESA-N
SMILESN=C(O)OC[C@H](CO)c1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • [(2S)-3-hydroxy-2-phenylpropyl] carbamate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3612845
  • SCHEMBL8089944

Physico-Chemical properties

IUPAC name[(2S)-3-hydroxy-2-phenylpropyl] carbamate
Molecular formulaC10H13NO3
Molecular weight195.215
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity53.24
LogP1.4
Topological polar surface area73.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.