ContaminantDB: benserazide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 11:02:09 UTC

Update Date

2016-11-09 01:22:56 UTC

Accession Number

CHEM043545

Identification

Common Name

benserazide

Class

Small Molecule

Description

A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benserazida	ChEBI
Benserazidum	ChEBI
DL-Serine 2-(2,3,4-trihydroxybenzyl)hydrazide	ChEBI
DL-Serine 2-[(2,3,4-trihydroxyphenyl)methyl]hydrazide	ChEBI
Ro 4-4602	ChEBI
Ro 44602	ChEBI
Seryltrihydroxy benzylhydrazine	HMDB
Serazide	HMDB
DL-Serine 2-((2,3,4-trihydroxyphenyl)methyl)hydrazide	HMDB
Benzylhydrazine, seryltrihydroxy	HMDB
Seryltrihydroxybenzylhydrazine	HMDB

Chemical Formula

C₁₀H₁₅N₃O₅

Average Molecular Mass

257.246 g/mol

Monoisotopic Mass

257.101 g/mol

CAS Registry Number

322-35-0

IUPAC Name

2-amino-3-hydroxy-N-[(2,3,4-trihydroxyphenyl)methyl]propanehydrazonic acid

Traditional Name

serazide

SMILES

NC(CO)C(O)=NNCC1=C(O)C(O)=C(O)C=C1

InChI Identifier

InChI=1S/C10H15N3O5/c11-6(4-14)10(18)13-12-3-5-1-2-7(15)9(17)8(5)16/h1-2,6,12,14-17H,3-4,11H2,(H,13,18)

InChI Key

BNQDCRGUHNALGH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine 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

Serine and derivatives

Alternative Parents

Substituents

Serine or derivatives
5-unsubstituted pyrrogallol
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid hydrazide
Polyol
Alcohol
Primary amine
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbohydrazide (CHEBI:64187 )
catechols (CHEBI:64187 )
primary alcohol (CHEBI:64187 )
primary amino compound (CHEBI:64187 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	3.6 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-3.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.51	ChemAxon
pKa (Strongest Basic)	8.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	151.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.75 m³·mol⁻¹	ChemAxon
Polarizability	25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9410000000-042a7ca62eb315395c77	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00kr-0900000000-36834aa07db9235c3d01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-1900000000-8d4a2c0c0f171ebdfaf2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-3900000000-43ed8993954a8a907fb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-052r-4900000000-30c8b3fbb72c084ed088	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4r-4900000000-d37ca07746ea74f04793	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-4900000000-9ecd00c168fa7c0fbbd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-147a530b86fcb416278a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-5900000000-37e67e92809b1668705e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-7900000000-ce0ce4287ecbaecc1e1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-9600000000-ab3f3ce953e99425942e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000i-7900000000-ebf2861d4c7b8aae2b9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000i-5900000000-7b957373e3070a778b62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-000i-9600000000-adcfd466b0d296a9b58b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00kr-0900000000-a9d526da65e0fba24627	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4r-4900000000-b03eee12455443701bc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-052r-4900000000-7c72b04c2544f21fae06	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-1900000000-8647a97e2d3494b10083	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000i-3900000000-28dcdb68549f4875aa71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-4900000000-c595311251e99a97ab23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066u-2960000000-c9bb547ca96568a2ce7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-3950000000-1d7dadf0170f0e776594	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08gr-6900000000-ae3f6090b51d2d032515	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ar9-2790000000-9ac39c097e6cb191c55e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05r9-5950000000-8e4e62872363996b5924	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r00-9400000000-00d50e32e481b0adecc6	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB12783

HMDB ID

HMDB0248960

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

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12703659

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22236652

3. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.

benserazide (CHEM043545)

Structure for CHEM043545: benserazide