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(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

PubChem CID
721860
Structure
(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid_small.png
(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 2799-15-7
  • D-alpha-Methyl DOPA
  • D-Methyldopa
  • (2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
  • Methyldopa, D-
Molecular Weight
211.21 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-08
  • Modify:
    2025-01-11

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-D-aMeTyr(3-OH)-OH
Sequence
X
HELM
PEPTIDE1{[C[C@@](Cc1ccc(c(c1)O)O)(C(=O)O)N]}$$$$
IUPAC
alpha-methyl-3-hydroxy-D-tyrosine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2R)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

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-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

CJCSPKMFHVPWAR-SNVBAGLBSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C[C@@](CC1=CC(=C(C=C1)O)O)(C(=O)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C10H13NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 UNII

3.3.3 ChEMBL ID

3.3.4 Nikkaji Number

3.3.5 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
211.21 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-1.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
211.08445790 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
211.08445790 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
104 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
246
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Chemical Classes

4.2.1 Drugs

4.2.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic alpha-2 Receptor Agonists

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic alpha-2 Receptor Agonists

8 Toxicity

8.1 Toxicological Information

8.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because of the low levels of methyldopa in breastmilk, amounts ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants. No special precautions are required.

◉ Effects in Breastfed Infants

No acute or long-term adverse effects were reported in any 15 infants ranging in age from less than 1 week to 8 weeks of age whose mothers were taking oral methyldopa 0.25 to 1.5 grams daily.

◉ Effects on Lactation and Breastmilk

Methyldopa can increase serum prolactin and has caused galactorrhea. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed.

9 Associated Disorders and Diseases

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 ChemIDplus

13.2 NORMAN Suspect List Exchange Classification

13.3 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  5. Drugs and Lactation Database (LactMed)
  6. Japan Chemical Substance Dictionary (Nikkaji)
  7. Springer Nature
  8. Therapeutic Target Database (TTD)
  9. Wikidata
  10. PubChem
  11. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
  14. NCBI
CONTENTS