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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO4
Molecular Weight 197.1879
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOPA, D-

SMILES

N[C@H](CC1=CC(O)=C(O)C=C1)C(O)=O

InChI

InChIKey=WTDRDQBEARUVNC-ZCFIWIBFSA-N
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-/m1/s1

HIDE SMILES / InChI
The D-form of dihydroxyphenylalanine (D-dopa) is a less physiologic activity than the L-form. D-dopa can be converted to the active L form during unidirectional chiral inversion, at first, oxidatively deaminated by D-amino acid oxidase to its alpha-keto acid and then transaminated by dopa transaminase to L-dopa. D-dopa is commonly used experimentally to determine whether the pharmacological effects of levodopa are stereospecific.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: d-dopa undergoes unidirectional chiral inversion and further suggest that D-dopa is first oxidatively deaminated by D-amino acid oxidas to its alpha-keto acid and then transaminated by dopa transaminase to L-dopa.
Unknown
Name Type Language
DOPA, D-
Systematic Name English
NSC-118368
Code English
DOPA D-FORM [MI]
Common Name English
LEVODOPA IMPURITY D [EP IMPURITY]
Common Name English
(2R)-2-AMINO-3-(3,4-DIHYDROXYPHENYL)PROPANOIC ACID
Systematic Name English
Code System Code Type Description
CHEBI
49169
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
PUBCHEM
92222
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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MERCK INDEX
m4739
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
227-343-0
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
NSC
118368
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
CHEBI
149689
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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WIKIPEDIA
D-DOPA
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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EPA CompTox
DTXSID70206673
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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CAS
5796-17-8
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
FDA UNII
8T862R29FY
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY