Levodopa
A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Levodopa are summarized together with 3D and 2D structures and relevant physico-chemical properties.
Table of Contents
What is the Levodopa?
The molecule Levodopa presents a molecular formula of C9H11NO4 and its IUPAC name is (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid.
Levodopa, also known as L-dopa, is a molecule that plays a critical role in the treatment of Parkinson's disease. Parkinson's disease is a neurological disorder that affects the central nervous system and is characterized by tremors, stiffness, and difficulty with movement. It is caused by a deficiency of the neurotransmitter dopamine in the brain..
Levodopa is a precursor to dopamine, which means that it is converted into dopamine in the body. It is taken orally and is able to cross the blood-brain barrier, allowing it to reach the brain and be converted into dopamine. This replenishment of dopamine can help to improve the symptoms of Parkinson's disease, including tremors, stiffness, and difficulty with movement..
Levodopa is often used in combination with other medications, such as carbidopa, which helps to increase its effectiveness and reduce the side effects. Common side effects of levodopa include nausea, vomiting, and dizziness..
Levodopa has been used to treat Parkinson's disease for over 50 years and is considered the most effective medication for the treatment of this condition. It is also used to treat other neurological disorders, including restless leg syndrome and attention deficit hyperactivity disorder (ADHD)..
Summary
From all the above, levodopa is a critical molecule in the treatment of Parkinson's disease and other neurological disorders. While it is effective at improving symptoms, it is important to carefully monitor its use and be aware of potential side effects..
3D structure
Cartesian coordinates
Geometry of Levodopa in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.
2D drawing
Molecule descriptors
| IUPAC name | (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid |
| InChI code | InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1 |
| InChI Key | WTDRDQBEARUVNC-LURJTMIESA-N |
| SMILES | N[C@@H](Cc1ccc(O)c(O)c1)C(=O)O |
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.
- (-)-(3,4-Dihydroxyphenyl)alanine
- (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
- (-)-Dopa
- (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
- (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
- (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidL-dopa
- (S)-2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid
- (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
- .beta.-(3, 4-Dihydroxyphenyl)alanine
- .beta.-(3,4-Dihydroxyphenyl)-L-alanine
- .beta.-(3,4-Dihydroxyphenyl)alanine
- 122769-74-8
- 1E83F927-C221-46AA-B90A-81B33C5F3868
- 3, 4-Dihydroxy-L-phenylalanine
- 3, 4-Dihydroxyphenylalanine
- 3,4-Dihydroxyphenyl-L-alanine
- 3,4-Dihydroxyphenylalanine
- 3,4-dihydroxy-L-phenylalanine
- 3-(3,4-Dihydroxyphenyl)-L-alanine
- 3-Hydroxy-L-tyrosine
- 4-dihydroxyphenylalanine
- 46627O600J
- 59-92-7
- 59L927
- 65170-01-6
- A832543
- AB00052418-06
- AB00052418-07
- AB00052418_08
- AB00052418_09
- AC-8432
- AM82124
- AS-13287
- Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-
- Alanine, 3-(3,4-dihydroxyphenyl)-
- Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-
- Alanine,4-dihydroxyphenyl)-
- Alanine,4-dihydroxyphenyl)-, (-)-
- Alanine,4-dihydroxyphenyl)-, L-
- Atamet
- BDBM50130192
- BDBM60928
- BIDD:GT0158
- BP-12850
- BPBio1_000059
- BSPBio_000053
- BSPBio_002354
- Bendopa
- Biodopa
- Brocadopa
- C00355
- C9H11NO4
- CARBILEV COMPONENT LEVODOPA
- CCG-39571
- CCRIS 3766
- CORBILTA COMPONENT LEVODOPA
- CS-1945
- CVT-301
- Carbidopa EP Impurity A
- Cerepap
- Cidandopa
- D 9628
- D00059
- D0600
- D70595
- D9628
- DB01235
- DHIVY COMPONENT LEVODOPA
- DOPA, L-
- DOPASNAP COMPONENT LEVODOPA
- DSSTox_CID_3209
- DSSTox_GSID_23209
- DSSTox_RID_76926
- DUOPA COMPONENT LEVODOPA
- Deadopa
- Dihydroxy-L-phenylalanine
- DivK1c_000452
- Dopa
- Dopaflex
- Dopaidan
- Dopal-fher
- Dopalina
- Dopar
- Doparkine
- Doparl
- Dopasol
- Dopaston
- Dopaston SE
- Dopastone
- Dopastral
- Dopicar
- Doprin
- EU-0100454
- Eldopal
- Eldopar
- Eldopatec
- Epitope ID:150927
- Eurodopa
- F0347-4695
- GTPL3639
- H-Phe{3,4-(OH)2}-OH
- HMS1568C15
- HMS1922J14
- HMS2090O08
- HMS2093N04
- HMS2095C15
- HMS2230B04
- HMS3261K10
- HMS3712C15
- HMS501G14
- HSDB 3348
- HY-N0304
- Helfo DOPA
- Helfo-Dopa
- IDI1_000452
- IPX-203 COMPONENT LEVODOPA
- IPX203 COMPONENT LEVODOPA
- Inbrija
- Inbrija (levodopa inhalation powder)
- Insulamina
- KBio1_000452
- KBio2_000934
- KBio2_003502
- KBio2_006070
- KBioGR_001177
- KBioSS_000934
- L Dopa
- L(-)-Dopa
- L-(-)-Dopa
- L-(3, 4-Dihydroxyphenyl)-.alpha.-alanine
- L-(3, 4-Dihydroxyphenyl)alanine
- L-(3,4-Dihydroxyphenyl)-.alpha.-alanine
- L-(3,4-Dihydroxyphenyl)alanine
- L-(o-Dihydroxyphenyl)alanine
- L-.beta.-(3,4-Dihydroxyphenyl)alanine
- L-3
- L-3,4-Dihydrophenylalanine
- L-3,4-Dihydroxyphenylalanine
- L-3-(3,4-Dihydroxyphenyl)alanine
- L-3-(3,4-dihydroxy-phenyl)alanine
- L-3-(3,4-dihydroxyphenyl)-Alanine
- L-3-Hydroxytyrosine
- L-4-5-Dihydroxyphenylalanine
- L-DOPA; Levodopa
- L-Dihydroxyphenylalanine
- L-Methyldopa ; (2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid; 3-(3,4-Dihydroxyphenyl)-?-methyl-L-alanine; 3-Hydroxy-a-methyl-L-tyrosine
- L-O-Dihydroxyphenylalanine
- L-Tyrosine, 3-hydroxy-
- L-Tyrosine, 3-hydroxy-, homopolymer
- L-b-(3,4-Dihydroxyphenyl)-a-alanine
- L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
- L-beta-(3,4-Dihydroxyphenyl)alanine
- L-dopa
- L-o-Hydroxytyrosine
- LEVODOPA COMPONENT OF CARBILEV
- LEVODOPA COMPONENT OF CORBILTA
- LEVODOPA COMPONENT OF DHIVY
- LEVODOPA COMPONENT OF DOPASNAP
- LEVODOPA COMPONENT OF DUOPA
- LEVODOPA COMPONENT OF LEVODOPA/CARBIDOPA/ENTACAPONE ORION
- LEVODOPA COMPONENT OF PARCOPA
- LEVODOPA COMPONENT OF RYTARY
- LEVODOPA COMPONENT OF SINEMET
- LEVODOPA COMPONENT OF STALEVO
- LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT LEVODOPA
- LP00454
- Laradopa
- Larodopa
- Ledopa
- Levedopa
- Levodopa
- Levodopa (JP15/USP)
- Levodopa (JP17/USP/INN)
- Levodopa (Sinemet)
- Levodopa;3,4-Dihydroxyphenylalanine
- Levodopum
- Levopa
- Lopac-D-9628
- Lopac0_000454
- MFCD00002598
- MLS000028514
- Maipedopa
- N1648
- NCGC00015384-01
- NCGC00016270-01
- NCGC00016270-04
- NCGC00016270-06
- NCGC00016270-07
- NCGC00016270-09
- NCGC00016270-10
- NCGC00016270-22
- NCGC00093869-04
- NCGC00261139-01
- NINDS_000452
- NSC 118381
- NSC-118381
- NSC-759573
- NSC118381
- NSC759573
- PARCOPA COMPONENT LEVODOPA
- PDSP1_001541
- PDSP2_001525
- Parda
- Pardopa
- Pharmakon1600-02300205
- Prestwick0_000017
- Prestwick1_000017
- Prestwick2_000017
- Prestwick3_000017
- Prestwick_185
- Prodopa
- Prolopa
- Q-201294
- Q300989
- RYTARY COMPONENT LEVODOPA
- Ro 4-6316
- SBI-0050439.P003
- SDCCGMLS-0066924.P001
- SDCCGSBI-0050439.P004
- SMR000058312
- SPECTRUM2300205
- SR-01000075384
- SR-01000075384-1
- SR-01000075384-4
- SR-01000075384-6
- SR-01000075384-7
- STALEVO COMPONENT LEVODOPA
- Sobiodopa
- Syndopa
- V-1512
- Veldopa
- WLN: QVYZ1R CQ DQ
- WLN: QVYZ1R CQ DQ -L
- Weldopa
- Z1762772338
- alanine, 3-(3,4-dihydroxyphenyl)-, L-
- b-(3,4-Dihydroxyphenyl)-L-alanine
- b-(3,4-Dihydroxyphenyl)-a-L-alanine
- b-(3,4-Dihydroxyphenyl)alanine
- beta-(3,4-Dihydroxyphenyl)-L-alanine
- beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
- beta-(3,4-Dihydroxyphenyl)-alpha-alanine
- beta-(3,4-Dihydroxyphenyl)alanine
- bmse000322
- component of Sinemet
- dihydroxyphenylalanine
- levodopa
- s1726
Reference codes for other databases
There exist several different chemical codes commonly used in orded to identify molecules:- CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
- Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
- ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
- PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
- RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
- ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
- CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.
- ZINC895199
- CAS-59-92-7
- UNII-46627O600J
- AKOS010396267
- DTXSID9023209
- CHEMBL1009
- CHEBI:15765
- Tox21_110338
- Tox21_500454
- EINECS 200-445-2
- SPBio_000391
- SPBio_001974
- SCHEMBL22655
- Spectrum_000454
- Spectrum2_000496
- Spectrum4_000539
- Spectrum5_001899
Physico-Chemical properties
| IUPAC name | (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid |
| Molecular formula | C9H11NO4 |
| Molecular weight | 197.188 |
| Melting point (ºC) | |
| Boiling point (ºC) | |
| Density (g/cm3) | |
| Molar refractivity | 49.55 |
| LogP | 0.8 |
| Topological polar surface area | 103.8 |
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.