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Showing Compound Methyldopa (FDB028425)

Record Information
Version1.0
Creation date2011-09-21 01:39:36 UTC
Update date2015-07-21 06:59:25 UTC
Primary IDFDB028425
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyldopa
DescriptionMethyldopa or alpha-methyldopa (brand names Aldomet, Apo-Methyldopa, Dopamet, Novomedopa) is a centrally-acting adrenergic antihypertensive medication. Its use is now deprecated following introduction of alternative safer classes of agents. However it continues to have a role in otherwise difficult to treat hypertension and gestational hypertension (formerly known as pregnancy-induced hypertension).; Methyldopa is an aromatic-amino-acid decarboxylase inhibitor in animals and in man. Only methyldopa, the L-isomer of alpha-methyldopa, has the ability to inhibit dopa decarboxylase and to deplete animal tissues of norepinephrine. In man the antihypertensive activity appears to be due solely to the L-isomer. About twice the dose of the racemate (DL-alpha-methyldopa) is required for equal antihypertensive effect. Methyldopa has no direct effect on cardiac function and usually does not reduce glomerular filtration rate, renal blood flow, or filtration fraction. Cardiac output usually is maintained without cardiac acceleration. In some patients the heart rate is slowed. Normal or elevated plasma renin activity may decrease in the course of methyldopa therapy. Methyldopa reduces both supine and standing blood pressure. Methyldopa usually produces highly effective lowering of the supine pressure with infrequent symptomatic postural hypotension. Exercise hypotension and diurnal blood pressure variations rarely occur.; Methyldopa, in its active metabolite form, is a central alpha-2 receptor agonist. Using methyldopa leads to alpha-2 receptor-negative feedback to sympathetic nervous system (SNS) (centrally and peripherally), allowing peripheral sympathetic nervous system tone to decrease. Such activity leads to a decrease in total peripheral resistance (TPR) and cardiac output.; When introduced it was a mainstay of antihypertensive therapy, but its use has declined, with increased use of other safer classes of agents. One of its important present-day uses is in the management of pregnancy-induced hypertension, as it is relatively safe in pregnancy compared to other antihypertensive drugs. from wiki [HMDB]
CAS Number555-30-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP-2ALOGPS
logP-1.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.79 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13NO4
IUPAC name(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
InChI IdentifierInChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
InChI KeyCJCSPKMFHVPWAR-JTQLQIEISA-N
Isomeric SMILESC[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O
Average Molecular Weight211.2145
Monoisotopic Molecular Weight211.084457909
Classification
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Phenylpropane
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethyldopa, non-derivatized, GC-MS Spectrumsplash10-001i-0690000000-f54d986a8144f4a79b82Spectrum
GC-MSMethyldopa, non-derivatized, GC-MS Spectrumsplash10-001i-0690000000-f54d986a8144f4a79b82Spectrum
Predicted GC-MSMethyldopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-4900000000-739bef9b92ae61fa3997Spectrum
Predicted GC-MSMethyldopa, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03l3-6719300000-8507376d6ae27047f468Spectrum
Predicted GC-MSMethyldopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-01p2-3940000000-04fec0e15e79c768fdc72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-2910000000-5ab87bad3301cc12d6712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0wmi-5900000000-8d84c2b3f8d9068136682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0ik9-2900000000-f0762b6c346fb34404e52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014s-0910000000-ef3d681f544c504b6f072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014r-0900000000-a11a3fc0536274091e7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03y0-0900000000-20bad18343ec957bca952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-014r-0900000000-2a78e6a20d8599caab2b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014s-0910000000-db2e7c58eec2a2e9f25e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03y0-0900000000-4ee772845ee32a944db12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0002-1900000000-3efdf92a8af6e42965e22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0002-1900000000-4ba9f4555cda937d38832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-006t-1900000000-aa6c8ce94351767534b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0002-0900000000-cdcf4d0d2fe21483aac52021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4290000000-cdd2c737cabf0ee44d1f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9410000000-d1fa6c265dd8ca539a0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007d-6900000000-56bdd61262b97efe050b2016-08-03View Spectrum
NMRNot Available
ChemSpider ID35562
ChEMBL IDCHEMBL459
KEGG Compound IDC07194
Pubchem Compound ID38853
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11754
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMethyldopa
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference