Identification

Generic Name
2,3,-Dihydroxybenzoylserine
DrugBank Accession Number
DB02710
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 241.1974
Monoisotopic: 241.058637089
Chemical Formula
C10H11NO6
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeutrophil gelatinase-associated lipocalinNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hippuric acids
Alternative Parents
N-acyl-alpha amino acids / Serine and derivatives / Salicylamides / Benzoyl derivatives / Catechols / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Beta hydroxy acids and derivatives / Vinylogous acids / Secondary carboxylic acid amides
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Alpha-amino acid or derivatives / Aromatic homomonocyclic compound / Benzoyl / Beta-hydroxy acid / Carbonyl group / Carboxamide group / Carboxylic acid
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
L-serine derivative (CHEBI:17455)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
127658-43-9
InChI Key
VDTYHTVHFIIEIL-LURJTMIESA-N
InChI
InChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1
IUPAC Name
(2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid
SMILES
[H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=O

References

General References
Not Available
KEGG Compound
C04204
PubChem Compound
151483
PubChem Substance
46508900
ChemSpider
133509
ChEBI
17455
PDBe Ligand
DBS
PDB Entries
1l6m / 3by0 / 3cbc / 3k3l / 3t1d / 5adv / 6gi1 / 7sf6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.76 mg/mLALOGPS
logP0.33ALOGPS
logP0.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.12 m3·mol-1ChemAxon
Polarizability22.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7976
Blood Brain Barrier-0.8578
Caco-2 permeable-0.8222
P-glycoprotein substrateNon-substrate0.7003
P-glycoprotein inhibitor INon-inhibitor0.9734
P-glycoprotein inhibitor IINon-inhibitor0.9617
Renal organic cation transporterNon-inhibitor0.9479
CYP450 2C9 substrateNon-substrate0.7959
CYP450 2D6 substrateNon-substrate0.8431
CYP450 3A4 substrateNon-substrate0.6951
CYP450 1A2 substrateNon-inhibitor0.8293
CYP450 2C9 inhibitorNon-inhibitor0.9264
CYP450 2D6 inhibitorNon-inhibitor0.9444
CYP450 2C19 inhibitorNon-inhibitor0.9476
CYP450 3A4 inhibitorNon-inhibitor0.9625
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9863
Ames testNon AMES toxic0.8015
CarcinogenicityNon-carcinogens0.9447
BiodegradationReady biodegradable0.9542
Rat acute toxicity1.8194 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9915
hERG inhibition (predictor II)Non-inhibitor0.9508
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0390000000-1c8bd41059bced330983
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2920000000-bc9d7862d6e634ce299e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00n0-9500000000-dca0ea7939deb8a40bf0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0490000000-5529ba05e060a66aa481
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0nvm-2940000000-7ab5cdf84a6c5cab4263
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbl-9500000000-4a04c984745c207267b5

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Iron-trafficking protein involved in multiple processes such as apoptosis, innate immunity and renal development. Binds iron through association with 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderop...
Gene Name
LCN2
Uniprot ID
P80188
Uniprot Name
Neutrophil gelatinase-associated lipocalin
Molecular Weight
22587.915 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45