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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-03-17 14:11:07 UTC
Update Date2021-09-14 15:20:32 UTC
HMDB IDHMDB0011754
Secondary Accession Numbers
  • HMDB11754
Metabolite Identification
Common 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 (Wikipedia ).
Structure
Data?1582752947
Synonyms
ValueSource
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acidChEBI
(S)-(-)-alpha-MethyldopaChEBI
3-Hydroxy-alpha-methyl-L-tyrosineChEBI
Alpha MedopaChEBI
alpha-Methyl dopaChEBI
alpha-Methyl-beta-(3,4-dihydroxyphenyl)-L-alanineChEBI
alpha-Methyl-L-3,4-dihydroxyphenylalanineChEBI
alpha-MethyldihydroxyphenylalanineChEBI
alpha-MethyldopaChEBI
AlphamethyldopaChEBI
AMDChEBI
L(-)-beta-(3,4-Dihydroxyphenyl)-alpha-methylalanineChEBI
L-(-)-3-(3,4-Dihydroxyphenyl)-2-methylalanineChEBI
L-(-)-alpha-Methyl-beta-(3,4-dihydroxyphenyl)alanineChEBI
L-(alpha-MD)ChEBI
L-2-Amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acidChEBI
L-3-(3,4-Dihydroxyphenyl)-2-methylalanineChEBI
L-alpha-Methyl-3,4-dihydroxyphenylalanineChEBI
L-alpha-MethyldopaChEBI
L-Methyl dopaChEBI
Levo-3-(3,4-dihydroxyphenyl)-2-methylalanineChEBI
Methyl-L-dopaChEBI
Methyldopa anhydrousChEBI
MethyldopumChEBI
MetildopaChEBI
AldometKegg
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoateGenerator
(S)-(-)-a-MethyldopaGenerator
(S)-(-)-Α-methyldopaGenerator
3-Hydroxy-a-methyl-L-tyrosineGenerator
3-Hydroxy-α-methyl-L-tyrosineGenerator
a MedopaGenerator
Α medopaGenerator
a-Methyl dopaGenerator
Α-methyl dopaGenerator
a-Methyl-b-(3,4-dihydroxyphenyl)-L-alanineGenerator
Α-methyl-β-(3,4-dihydroxyphenyl)-L-alanineGenerator
a-Methyl-L-3,4-dihydroxyphenylalanineGenerator
Α-methyl-L-3,4-dihydroxyphenylalanineGenerator
a-MethyldihydroxyphenylalanineGenerator
Α-methyldihydroxyphenylalanineGenerator
a-MethyldopaGenerator
Α-methyldopaGenerator
L(-)-b-(3,4-Dihydroxyphenyl)-a-methylalanineGenerator
L(-)-Β-(3,4-dihydroxyphenyl)-α-methylalanineGenerator
L-(-)-a-Methyl-b-(3,4-dihydroxyphenyl)alanineGenerator
L-(-)-Α-methyl-β-(3,4-dihydroxyphenyl)alanineGenerator
L-(a-MD)Generator
L-(Α-MD)Generator
L-2-Amino-2-methyl-3-(3,4-dihydroxyphenyl)propionateGenerator
L-a-Methyl-3,4-dihydroxyphenylalanineGenerator
L-Α-methyl-3,4-dihydroxyphenylalanineGenerator
L-a-MethyldopaGenerator
L-Α-methyldopaGenerator
(-)-a-MethyldopaHMDB
(-)-alpha-MethyldopaHMDB
(-)-MethyldopaHMDB
2-Methyl-3-(3,4-dihydroxyphenyl)alanineHMDB
3,4-Dihydroxy-2-methylphenylalanine (acd/name 4.0)HMDB
a-Methyl-L-dopaHMDB, Generator
Aldoclor-150HMDB
Aldoclor-250HMDB
AldometilHMDB
Aldoril 15HMDB
Aldoril 25HMDB
Aldoril D30HMDB
Aldoril D50HMDB
alpha-Methyl-L-dopaHMDB, MeSH
apo Methyldopa tab 125MGHMDB
apo Methyldopa tab 250MGHMDB
apo Methyldopa tab 500MGHMDB
apo-MethyldopaHMDB, MeSH
Bayer 1440 LHMDB
BaypresolHMDB
BecantaHMDB
DopametHMDB, MeSH
DopamethyperpaxHMDB
DopatecHMDB
DopegytHMDB, MeSH
GrospiskHMDB
HyperpaxHMDB
HypolagHMDB
L(-)-a-MethylalanineHMDB
L(-)-alpha-MethylalanineHMDB
L-(-)-3-(3,4-Dihydroxyphenyl)-2-methyl-alanineHMDB
L-(-)-a-Methyl-a-methyl-aldominHMDB
L-(-)-alpha-Methyl-alpha-methyl-aldominHMDB
L-a-Methyl-(3, 4-dihydroxyphenyl)alanineHMDB
L-alpha-Methyl-(3, 4-dihydroxyphenyl)alanineHMDB
MedometHMDB
MedopaHMDB
MedopalHMDB
MedoprenHMDB
MethoplainHMDB
Methyldopa 125 tab 125MGHMDB
Methyldopa 250 tabHMDB
Methyldopa 500 tab 500MGHMDB
MethyldopateHMDB, MeSH
Methyldopate HCLHMDB
novo-Medopa tab 125MGHMDB
novo-Medopa tab 250MGHMDB
novo-Medopa tab 500MGHMDB
NovomedopaHMDB
Nu-medopaHMDB, MeSH
Nu-medopa tab 125MGHMDB
Nu-medopa tab 250MGHMDB
Nu-medopa tab 500MGHMDB
PresinolHMDB
PresolisinHMDB
SedometilHMDB
SembrinaHMDB, MeSH
Alphapharm brand OF methyldopaMeSH, HMDB
Apotex brand OF methyldopaMeSH, HMDB
Merck brand OF methyldopaMeSH, HMDB
Nu pharm brand OF methyldopaMeSH, HMDB
DopergitMeSH, HMDB
HydopaMeSH, HMDB
Merck sharp and dohme brand OF methyldopaMeSH, HMDB
Methyldopa orion brandMeSH, HMDB
Nu-pharm brand OF methyldopaMeSH, HMDB
Orion brand OF methyldopaMeSH, HMDB
Rhône poulenc rorer brand OF methyldopaMeSH, HMDB
Rhône-poulenc rorer brand OF methyldopaMeSH, HMDB
DopegitMeSH, HMDB
Methyldopa apotex brandMeSH, HMDB
Methyldopa biopat brandMeSH, HMDB
Methyldopa clonmel brandMeSH, HMDB
Methyldopa merck brandMeSH, HMDB
Nu medopaMeSH, HMDB
alpha Methyl L dopaMeSH, HMDB
alpha MethyldopaMeSH, HMDB
apo MethyldopaMeSH, HMDB
Biopat brand OF methyldopaMeSH, HMDB
Cahill may roberts brand OF methyldopaMeSH, HMDB
Clonmel brand OF methyldopaMeSH, HMDB
MeldopaMeSH, HMDB
Methyldopa alphapharm brandMeSH, HMDB
Methyldopa nu-pharm brandMeSH, HMDB
MethyldopaChEBI
Α-methyl-L-dopaGenerator, HMDB
Chemical FormulaC10H13NO4
Average Molecular Weight211.2145
Monoisotopic Molecular Weight211.084457909
IUPAC Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
Traditional Namemethyldopa
CAS Registry Number555-30-6
SMILES
C[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 at 25 °CNot Available
LogP-1.79MEYLAN,WM & HOWARD,PH (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.554http://allccs.zhulab.cn/database/detail?ID=AllCCS00001382
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.85831661259
DarkChem[M-H]-146.7931661259
DeepCCS[M+H]+145.9830932474
DeepCCS[M-H]-143.58530932474
DeepCCS[M-2H]-176.7930932474
DeepCCS[M+Na]+151.93730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethyldopaC[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O3388.4Standard polar33892256
MethyldopaC[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O1993.5Standard non polar33892256
MethyldopaC[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O2055.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyldopa,1TMS,isomer #1C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O2081.1Semi standard non polar33892256
Methyldopa,1TMS,isomer #2C[C@](N)(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O2058.6Semi standard non polar33892256
Methyldopa,1TMS,isomer #3C[C@](N)(CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C2109.0Semi standard non polar33892256
Methyldopa,1TMS,isomer #4C[C@@](CC1=CC=C(O)C(O)=C1)(N[Si](C)(C)C)C(=O)O2201.4Semi standard non polar33892256
Methyldopa,2TMS,isomer #1C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O2042.6Semi standard non polar33892256
Methyldopa,2TMS,isomer #2C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C2033.3Semi standard non polar33892256
Methyldopa,2TMS,isomer #3C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(N[Si](C)(C)C)C(=O)O2120.8Semi standard non polar33892256
Methyldopa,2TMS,isomer #4C[C@](N)(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2016.4Semi standard non polar33892256
Methyldopa,2TMS,isomer #5C[C@@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O2084.6Semi standard non polar33892256
Methyldopa,2TMS,isomer #6C[C@@](CC1=CC=C(O)C(O)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2131.5Semi standard non polar33892256
Methyldopa,2TMS,isomer #7C[C@](CC1=CC=C(O)C(O)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2333.0Semi standard non polar33892256
Methyldopa,3TMS,isomer #1C[C@](N)(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2063.2Semi standard non polar33892256
Methyldopa,3TMS,isomer #2C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O2111.8Semi standard non polar33892256
Methyldopa,3TMS,isomer #3C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2082.0Semi standard non polar33892256
Methyldopa,3TMS,isomer #4C[C@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2274.7Semi standard non polar33892256
Methyldopa,3TMS,isomer #5C[C@@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2056.4Semi standard non polar33892256
Methyldopa,3TMS,isomer #6C[C@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2264.2Semi standard non polar33892256
Methyldopa,3TMS,isomer #7C[C@](CC1=CC=C(O)C(O)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2290.5Semi standard non polar33892256
Methyldopa,4TMS,isomer #1C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2114.7Semi standard non polar33892256
Methyldopa,4TMS,isomer #1C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2115.0Standard non polar33892256
Methyldopa,4TMS,isomer #1C[C@@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C2150.7Standard polar33892256
Methyldopa,4TMS,isomer #2C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2300.3Semi standard non polar33892256
Methyldopa,4TMS,isomer #2C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2212.3Standard non polar33892256
Methyldopa,4TMS,isomer #2C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2378.5Standard polar33892256
Methyldopa,4TMS,isomer #3C[C@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2285.1Semi standard non polar33892256
Methyldopa,4TMS,isomer #3C[C@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2267.9Standard non polar33892256
Methyldopa,4TMS,isomer #3C[C@](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2289.7Standard polar33892256
Methyldopa,4TMS,isomer #4C[C@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2276.8Semi standard non polar33892256
Methyldopa,4TMS,isomer #4C[C@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2288.0Standard non polar33892256
Methyldopa,4TMS,isomer #4C[C@](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2328.8Standard polar33892256
Methyldopa,5TMS,isomer #1C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2373.6Semi standard non polar33892256
Methyldopa,5TMS,isomer #1C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2246.2Standard non polar33892256
Methyldopa,5TMS,isomer #1C[C@](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2162.3Standard polar33892256
Methyldopa,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@](C)(N)C(=O)O)C=C1O2343.4Semi standard non polar33892256
Methyldopa,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(C[C@](C)(N)C(=O)O)=CC=C1O2324.1Semi standard non polar33892256
Methyldopa,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O)C(O)=C12368.1Semi standard non polar33892256
Methyldopa,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C(O)=C1)C(=O)O2453.6Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12574.8Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@](C)(N)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2574.7Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O2667.6Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12536.3Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2648.1Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C2676.6Semi standard non polar33892256
Methyldopa,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N([C@@](C)(CC1=CC=C(O)C(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C2772.1Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@](C)(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12752.7Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C2815.0Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2847.6Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O3009.4Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2782.0Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2998.2Semi standard non polar33892256
Methyldopa,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2975.4Semi standard non polar33892256
Methyldopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C3012.3Semi standard non polar33892256
Methyldopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2851.4Standard non polar33892256
Methyldopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2613.2Standard polar33892256
Methyldopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3181.8Semi standard non polar33892256
Methyldopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3007.3Standard non polar33892256
Methyldopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2655.4Standard polar33892256
Methyldopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3220.9Semi standard non polar33892256
Methyldopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2936.4Standard non polar33892256
Methyldopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@](C)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2725.7Standard polar33892256
Methyldopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3161.6Semi standard non polar33892256
Methyldopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3025.6Standard non polar33892256
Methyldopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2687.3Standard polar33892256
Methyldopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3408.0Semi standard non polar33892256
Methyldopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3128.9Standard non polar33892256
Methyldopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@](C)(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2667.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyldopa GC-EI-TOF (Non-derivatized)splash10-001i-0690000000-f54d986a8144f4a79b822017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyldopa GC-EI-TOF (Non-derivatized)splash10-001i-0690000000-f54d986a8144f4a79b822018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyldopa GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-4900000000-739bef9b92ae61fa39972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyldopa GC-MS (3 TMS) - 70eV, Positivesplash10-03l3-6719300000-8507376d6ae27047f4682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyldopa GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa LC-ESI-qTof , Positive-QTOFsplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa , positive-QTOFsplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 15V, Negative-QTOFsplash10-01p2-3940000000-04fec0e15e79c768fdc72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 30V, Negative-QTOFsplash10-0002-2910000000-5ab87bad3301cc12d6712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 90V, Positive-QTOFsplash10-0wmi-5900000000-8d84c2b3f8d9068136682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 75V, Positive-QTOFsplash10-0ik9-2900000000-f0762b6c346fb34404e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 15V, Positive-QTOFsplash10-014s-0910000000-ef3d681f544c504b6f072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 30V, Positive-QTOFsplash10-014r-0900000000-a11a3fc0536274091e7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 60V, Positive-QTOFsplash10-03y0-0900000000-20bad18343ec957bca952021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 45V, Positive-QTOFsplash10-014r-0900000000-2a78e6a20d8599caab2b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 15V, Positive-QTOFsplash10-014s-0910000000-db2e7c58eec2a2e9f25e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 60V, Positive-QTOFsplash10-03y0-0900000000-4ee772845ee32a944db12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 60V, Positive-QTOFsplash10-0002-1900000000-3efdf92a8af6e42965e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 60V, Negative-QTOFsplash10-0002-1900000000-4ba9f4555cda937d38832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 45V, Negative-QTOFsplash10-006t-1900000000-aa6c8ce94351767534b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyldopa 75V, Negative-QTOFsplash10-0002-0900000000-cdcf4d0d2fe21483aac52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 10V, Positive-QTOFsplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 20V, Positive-QTOFsplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 40V, Positive-QTOFsplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 10V, Positive-QTOFsplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 20V, Positive-QTOFsplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 40V, Positive-QTOFsplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 10V, Negative-QTOFsplash10-03di-4290000000-cdd2c737cabf0ee44d1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 20V, Negative-QTOFsplash10-000i-9410000000-d1fa6c265dd8ca539a0e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyldopa 40V, Negative-QTOFsplash10-007d-6900000000-56bdd61262b97efe050b2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDDB00968
Phenol Explorer Compound IDNot Available
FooDB IDFDB028425
KNApSAcK IDC00040542
Chemspider ID35562
KEGG Compound IDC07194
BioCyc IDALPHA-METHYLDOPA
BiGG IDNot Available
Wikipedia LinkMethyldopa
METLIN IDNot Available
PubChem Compound38853
PDB IDNot Available
ChEBI ID61058
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iyer KS, Thampuran RV: Beta blockade and anticonvulsant activity of propranolol. Indian J Physiol Pharmacol. 1978 Jul-Sep;22(3):293-6. [PubMed:721251 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Methyldopa → (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Methyldopa → 6-{5-[(2S)-2-amino-2-carboxy-2-methylethyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Methyldopa → 6-{4-[(2R)-2-amino-2-carboxy-2-methylethyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Methyldopa → (2S)-2-amino-3-[4-hydroxy-3-(sulfooxy)phenyl]-2-methylpropanoic aciddetails