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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
D-dopa is unidirectionally converted to L-dopa by D-amino acid oxidase, followed by dopa transaminase.
2006 Nov

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
PRIMARY
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