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Compound InformationSONAR Target prediction
Name:

L-3,4-Dihydroxyphenylalanine

Unique Identifier:LOPAC 00283
MolClass: Checkout models in ver1.5 and ver1.0
Molecular Formula:C9H11NO4
Molecular Weight:189.124 g/mol
X log p:5.101  (online calculus)
Lipinksi Failures1
TPSA17.07
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptors Count:5
Rotatable Bond Count:3
Canonical Smiles:NC(Cc1ccc(O)c(O)c1)C(O)=O
Class:Dopamine
Action:Precursor
Generic_name:Levodopa
Chemical_iupac_name:2-amino-3-(3,4-dihydroxyphenyl)-propanoic acid
Drug_type:Approved Drug
Pharmgkb_id:PA450213
Kegg_compound_id:C00355
Drugbank_id:APRD00309
Melting_point:276-278 oC
H2o_solubility:5000 mg/L
Logp:-2.244
Isoelectric_point:2.32
Cas_registry_number:59-92-7
Mass_spectrum:http://webbook.nist.gov/cgi/cbook.cgi?Spec=C59927&Index=0&Type=Mass&Large=on
Drug_category:Dopamine Agents; Antiparkinson Agents; Antidyskinetics; ATC:N04BA01; ATC:N04BA04
Indication:For the treatment of idiopathic Parkinson-s disease (Paralysis Agitans),
postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to
the nervous system by carbon monoxide intoxication, and manganese intoxication.
Pharmacology:Levodopa (L-dopa) is used to replace dopamine lost in Parkinson-s disease because
dopamine itself cannot cross the blood-brain barrier where its precursor can.
However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so
it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as
carbidopa, without which 90% is metabolised in the gut wall, and with a COMT
inhibitor if possible; this prevents about a 5% loss. The form given therapeutically
is therefore a prodrug which avoids decarboxylation in the stomach and periphery,
can cross the blood-brain barrier, and once in the brain is converted to the
neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase.
Mechanism_of_action:Striatal dopamine levels in symptomatic Parkinson-s disease are decreased by 60 to
80%, striatal dopaminergic neurotransmission may be enhanced by exogenous
supplementation of dopamine through administration of dopamine-s precursor,
levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier
and is decarboxylated to dopamine. This newly formed dopamine then is available to
stimulate dopaminergic receptors, thus compensating for the depleted supply of
endogenous dopamine.
Organisms_affected:Humans and other mammals

Found: 24 nonactive as graph: single | with analogs [1] << Back 1 2 3 4 5 6 7 8 9 10  Next >> [24]
Species: 4932
Condition: GIM3
Replicates: 4
Raw OD Value: r im 0.5224±0.0408753
Normalized OD Score: sc h 0.9895±0.0220109
Z-Score: -0.1848±0.503099
p-Value: 0.797706
Z-Factor: -5.55408
Fitness Defect: 0.226
Bioactivity Statement: Nonactive
Experimental Conditions
Library:Lopac
Plate Number and Position:6|F5
Drug Concentration:50.00 nM
OD Absorbance:600 nm
Robot Temperature:27.50 Celcius
Date:2005-04-08 YYYY-MM-DD
Plate CH Control (+):0.0457875±0.00848
Plate DMSO Control (-):0.6833750000000001±0.14634
Plate Z-Factor:-0.0275
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DBLink | Rows returned: 182 3 Next >> 
836 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
4138 2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoic acid
6047 (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
22040 [1-carboxy-2-(3,4-dihydroxyphenyl)ethyl]azanium chloride
38852 (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoic acid trihydrate
38853 (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoic acid

internal high similarity DBLink | Rows returned: 5
RJC 01671 0.9464
LOPAC 00613 1.0000
LOPAC 01063 1.0000
SPE01500403 1.0000
SPE02300205 1.0000

active | Cluster 12980 | Additional Members: 10 | Rows returned: 2
SPE01502206 0.55
LOPAC 01089 0.55

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