Identification

Name
Oxamic Acid
Accession Number
DB03940  (EXPT02460)
Type
Small Molecule
Groups
Experimental
Description

Amino-substituted glyoxylic acid derivative. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-47001 / NSC-49416 / NSC-53102
Categories
UNII
QU60N5OPLG
CAS number
471-47-6
Weight
Average: 89.0501
Monoisotopic: 89.011292967
Chemical Formula
C2H3NO3
InChI Key
SOWBFZRMHSNYGE-UHFFFAOYSA-N
InChI
InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)
IUPAC Name
carbamoylformic acid
SMILES
NC(=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UL-lactate dehydrogenaseNot AvailablePlasmodium falciparum (isolate CDC / Honduras)
UL-lactate dehydrogenaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UL-lactate dehydrogenase A chainNot AvailableHuman
UL-lactate dehydrogenase B chainNot AvailableHuman
UFormate acetyltransferase 1Not AvailableEscherichia coli (strain K12)
UD-lactate dehydrogenaseNot AvailableLactobacillus helveticus
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Shinsuke Shirakawa, Kazunori Kanda, Mitsuo Yamada, Kei Aoki, Satoshi Urano, Nobuaki Tomita, "Compound containing an oxamic acid group, a process for producing the compound, and a resin composition containing the compound." U.S. Patent US5663262, issued August, 1987.

US5663262
General References
Not Available
External Links
KEGG Compound
C01444
PubChem Compound
974
PubChem Substance
46507735
ChemSpider
949
BindingDB
23222
ChEBI
18058
ChEMBL
CHEMBL15976
HET
OXM
PDB Entries
1a5z / 1h17 / 1i0z / 1i10 / 1ldg / 1ldm / 1ldn / 1lth / 1oc4 / 1t2e
show 24 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)210 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility108.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.26 m3·mol-1ChemAxon
Polarizability6.65 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8047
Blood Brain Barrier+0.9244
Caco-2 permeable-0.8392
P-glycoprotein substrateNon-substrate0.8645
P-glycoprotein inhibitor INon-inhibitor0.9828
P-glycoprotein inhibitor IINon-inhibitor0.99
Renal organic cation transporterNon-inhibitor0.9803
CYP450 2C9 substrateNon-substrate0.8713
CYP450 2D6 substrateNon-substrate0.8657
CYP450 3A4 substrateNon-substrate0.7818
CYP450 1A2 substrateNon-inhibitor0.9675
CYP450 2C9 inhibitorNon-inhibitor0.9667
CYP450 2D6 inhibitorNon-inhibitor0.9565
CYP450 2C19 inhibitorNon-inhibitor0.9694
CYP450 3A4 inhibitorNon-inhibitor0.9764
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9972
Ames testNon AMES toxic0.8384
CarcinogenicityNon-carcinogens0.781
BiodegradationReady biodegradable0.8507
Rat acute toxicity1.0426 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.999
hERG inhibition (predictor II)Non-inhibitor0.9862
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
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-01b9-4900000000-a5c7d6900f929f7102bf
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-b801e8d1b363f91332ad
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-45810f38453748a2d26f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-68b3969cef554dca4e23
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-785f3a8aab8f2ac5f598
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-4f5256271ccf6a7d0e19
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-1348db048c59f511f37f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-7ed633dbb477c19204b2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-f3903e56dedef1549964
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-e87e076e2ffe6d08a16b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000f-9000000000-b870b26a5ebffe4dffa5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-371fe3b6dd3cc4f2cd1a

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Primary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alpha-amino acid or derivatives / Primary carboxylic acid amide / Carboxamide group / Monocarboxylic acid or derivatives / Carboxylic acid / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
dicarboxylic acid monoamide (CHEBI:18058)

Targets

Kind
Protein
Organism
Plasmodium falciparum (isolate CDC / Honduras)
Pharmacological action
Unknown
General Function
L-lactate dehydrogenase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q27743
Uniprot Name
L-lactate dehydrogenase
Molecular Weight
34107.505 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
L-malate dehydrogenase activity
Specific Function
Not Available
Gene Name
ldh
Uniprot ID
P16115
Uniprot Name
L-lactate dehydrogenase
Molecular Weight
34994.11 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Not Available
Gene Name
LDHA
Uniprot ID
P00338
Uniprot Name
L-lactate dehydrogenase A chain
Molecular Weight
36688.465 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Not Available
Gene Name
LDHB
Uniprot ID
P07195
Uniprot Name
L-lactate dehydrogenase B chain
Molecular Weight
36638.225 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Formate c-acetyltransferase activity
Specific Function
Not Available
Gene Name
pflB
Uniprot ID
P09373
Uniprot Name
Formate acetyltransferase 1
Molecular Weight
85356.555 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Lactobacillus helveticus
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P30901
Uniprot Name
D-lactate dehydrogenase
Molecular Weight
37778.94 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. [PubMed:17139284]
  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. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine...
Gene Name
SLC16A3
Uniprot ID
O15427
Uniprot Name
Monocarboxylate transporter 4
Molecular Weight
49468.9 Da
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:29