Droxidopa (CED0008820)

Record Information

Version

1.0

Creation Date

2016-05-22 05:43:55 UTC

Update Date

2026-05-14 18:19:09 UTC

Accession Number

CHEM018979

Identification

Common Name

Droxidopa

Class

Small Molecule

Description

Droxidopa is an organic compound with the chemical formula C9H11NO5 and an average molecular weight of 213.19 g/mol. Droxidopa belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified in six recorded sources, including healthcare, pharmaceuticals and veterinary products specifically as cardiac stimulants excluding cardiac glycosides, as well as electrical and electronic equipment such as antennas, and building and construction materials including ceilings, fencing, ladders, stairs and ramps. The recorded route of exposure for this substance is oral. In terms of biological activity, there are 10 recorded protein targets for droxidopa. It acts as an agonist or inhibitor of phenylalanine-4-hydroxylase (PAH) as well as the alpha-1A adrenergic receptor (ADRA1A), alpha-1B adrenergic receptor (ADRA1B), and alpha-1D adrenergic receptor (ADRA1D), among 6 other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₉H₁₁NO₅

Average Molecular Mass

213.189 g/mol

Monoisotopic Mass

213.064 g/mol

CAS Registry Number

23651-95-8

IUPAC Name

(2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Traditional Name

(2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

SMILES

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

InChI Identifier

InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8-/m0/s1

InChI Key

QXWYKJLNLSIPIN-YUMQZZPRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
L-alpha-amino acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Aralkylamine
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Carboxylic acid salt
Amino acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Alcohol
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic alcohol
Primary aliphatic amine
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	15.3 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.7	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	8.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	124.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.29 m³·mol⁻¹	ChemAxon
Polarizability	19.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03xs-1940000000-49d3ab08facb36017b34	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gbi-0900000000-312868d7bf126893fc30	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pir-8900000000-f834c172576e3edf3a02	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1890000000-c4c4af9f3c2041485e7b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0609-3910000000-55ca6672a13cc77a9e4d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9200000000-d2a8d81d0eb1ccb859c7	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8883.0	Log mg/kg	[5000:16000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
286	Cardiac stimulants excl. cardiac glycosides	Healthcare, pharmaceuticals & veterinary products	Not Available
495	Ceilings	Building & Construction	Not Available
496	Fencing	Building & Construction	Not Available
498	Ladders	Building & Construction	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Alpha-2A adrenergic receptor	Q01338	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Alpha-2C adrenergic receptor	Q01337	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	10.4318
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	16.504
Click to view 3D structure	Beta-1 adrenergic receptor	B0FL73	Cavia porcellus	Predicted (SEA)	5.99439
Click to view 3D structure	Beta-2 adrenergic receptor	Q8K4Z4	Cavia porcellus	Predicted (SEA)	8.25202
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	43.907
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	62.5908
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	1.32344
Click to view 3D structure	Taste receptor type 2 member 50	P59544	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 45	P59539	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 42	Q7RTR8	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 41	P59536	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 7	Q9NYW3	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 30	P59541	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 60	P59551	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 19	P59542	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 20	P59543	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 1	Q9NYW7	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 40	P59535	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 3	Q9NYW6	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 13	Q9NYV9	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 39	P59534	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 5	Q9NYW4	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Taste receptor type 2 member 9	Q9NYW1	Humans	Predicted (SEA)	1.08989

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

6999029

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Droxidopa (CED0008820)

Structure for CHEM018979: Droxidopa

No pathways found

Structure